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Destinations by Maptech 2026

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Discover Luxury in the Florida Keys

Dock with Confidence. Stay in Comfort.

• Accommodating vessels up to 115’ wet & 50’ dry – Largest forklift in the Lower Keys

• 24-Hour Security – Your vessel’s safety is our priority

• Hurricane Storage Rated to 150 mph

• Diesel & REC-90 Fuel – Convenient fueling on-site

• Free In-slip Pump Out Services – Keeping our waters pristine

• Best Views in the Lower Keys – Unmatched beauty and serenity

• Seconds from the Atlantic Ocean – Easy access to world-class boating & fishing

Amenities That Set Us Apart

• Resort Style Pool & Private Beach

• Relax and unwind at the Crescent Tiki with new grills, lounge chairs and dining tables

• Ship’s Store – Essentials, snacks and gear available

• Laundry & Shower Facilities – Freshen up after a day on the water

• WiFi Access – Stay connected at the dock

PRESIDENT

Lee Estes

EDITOR

Christopher B. Garrity

GRAPHIC DESIGN

Kristine Rothaupt, Inclined to Design

GRAPHICS MANAGER

Roxanne Castaldy

ADVERTISING SALES

Dibbon Joy

Joy McPeters

CONTRIBUTING EDITORS

Angela Rachmaciej

Ted Shanstrom

Destinations by

OFFICE MANAGER

Penny Raimondo

destinations

ADVERTISING COORDINATOR

Nancy Pereira Nieves

WAREHOUSE COORDINATOR

Steven Gauthier

AERIAL PHOTOGRAPHY

We’d like to welcome you to our 50th anniversary party with this milestone magazine!

What started as the passion project of a boater-turnedchartmaker has evolved into a business with more than a hundred products being published by Maptech. This magazine celebrates our milestone with 50 of the most popular yachting destinations along the East Coast — plus some bonus ports of call in the Bahamas and Caribbean.

Destinations

Tom Walsh, Shoreline Aerial Photography

INFORMATION TECHNOLOGY

Eric Nelson

Tony Zilla

©Maptech. All rights reserved. No part of this publication may be reproduced in full or in part, or used in any form or by any means — graphic, electronic, or mechanical including photocopying, recording, taping, or information storage-and-retrieval systems — without the written permission of the publisher.

Maptech has made every effort to ensure the accuracy of the information in this magazine. However, Maptech makes no warranty or guarantee for any use of the information contained herein. Similarly, inclusion in this magazine of such things as marine facilities and services, restaurants, places of interest, attractions or activities is for informational purposes only, and no guarantee is provided as to their accuracy or current status, nor are they all recommended. Neither Maptech, nor any of its officers, employees, or agents shall in any way be responsible for any consequential, incidental, or exemplary loss or damage resulting from the use or misuse of any material in this magazine.

© 2026 EDGEWATER MARINE INDUSTRIES, LLC dba: MAPTECH 90 Hatch Street, 1st Floor New Bedford, MA 02745 508-990-9020 production@maptech.com maptech.com

It all started in the 1970s when commercial printer Frank Nappa came up with a way to reproduce cumbersome government charts into an easy-touse, spiral-bound ChartKit® — at a cost that was far below what someone would have to spend on individual charts. Well over a million ChartKit® books have sold in five decades.

ChartKit® was purchased in the late 1990s by Maptech, which also owned Embassy Cruising Guides, Maptech Waterproof Charts, and Maptech navigation software. Years later, as a former ChartKit® employee and then the owner of Richardsons’ Chartbook & Cruising Guides for the Great Lakes, I purchased all of them; thus, we became one big family again.

This special Destinations magazine commemorating our 50th anniversary highlights the top places and events along the East Coast. Use it as a cruising companion for boating from Maine to western Florida as well as the Bahamas, Puerto Rico and the Virgin Islands

We express our deep gratitude to our business partners, our advertisers, our staff and, most important, our customers. This extraordinary milestone was made possible by all of you. Your trust and support have been the driving force behind our continued success, and there simply would be no Maptech without you.

Our organization’s goals have not changed much since its founding. We continue to offer a blend of time-tested, traditional publications like printed nautical charts and cruising guides along with contemporary resources like digital navigation software and coastal drone videos.

I’m honored to continue the legacy that started with ChartKit,® ensuring that Maptech remains the essential resource for boaters. We look forward to seeing what the next decades bring us.

6

NEW ENGLAND

From Bar Harbor to Block Island, highlights of 15 places where one should go on an adventure.

6 74 62 34 50 94 98

34

LONG ISLAND SOUND

Nine harbors to experience from New York City to Greenport, including the best of Connecticut.

50

CHESAPEAKE

From Baltimore to Norfolk, seven exciting escapades to explore in the Chesapeake Bay.

62

SOUTHEAST

Five premier ports of call in North Carolina, South Carolina and Georgia to discover.

74

FLORIDA

From Fernandina Beach to Key West and the Gulf Coast, 14 Sunshine State spots.

94

BAHAMAS

Highlights five bonus Destinations within a watery Eden of nearly 100,000 square miles.

98

VIRGIN ISLANDS & PUERTO RICO

Spotlights a few extra Destinations within the treasure-trove of the northeastern Caribbean.

On the cover: Provincetown Marina Photo courtesy of Ocean Havens/Jonah Gouin

George Washington ordered construction of America’s first lighthouse at Portland Head in 1787 when Maine was part of Massachusetts.

New England

Rugged coasts, historic harbors and classic charm

The waters and harbors of New England are a virtual paradise for boaters. Temperate summer winds, stimulating currents and superb harbors of infinite variety dot the coast from Block Island to Maine. A cruiser would have to spend dozens of summers to visit all of New England’s boating destinations.

Narragansett Bay and Buzzards Bay feature destinations both lively and quiet, with Newport and offshore Block Island being two of the most popular ports of call on the Atlantic seaboard. To the east, Martha’s Vineyard, Nantucket and Hyannis are noteworthy as well.

Farther north, Cape Cod Bay is where you’ll find Provincetown and Plymouth, two ports where the Pilgrims came ashore. Boston, the largest city in New England, is a day sail away. Marblehead, Gloucester and the Merrimack River are less than 50 miles from the Massachusetts capital.

New Hampshire has the shortest coastline of any U.S. state on the ocean. Fishing vessels dominate its small ports of Seabrook, Hampton and Rye, while Portsmouth buzzes with nightlife and excellent restaurants just across the Piscataqua River from Kittery, Maine, where retail outlets lure many.

Portland and southern Maine ease you into the distinctive Maine lifestyle. You could spend decades exploring the Pine Tree State’s crannied coast. It is a nautical dream come true. There are areas where only a few lobstermen live; other spots bustle with activities, from weekly regattas to world-famous shopping. This coastal cornucopia mixes sandy beaches and rocky shores, frigid waters and tepid swimming holes, ranges of mountains and plains of salt marsh. Most of the Maine coast is so empty, so elemental and filled with nature’s glory, that you easily fall under its spell and forget you ever had any cares.

ABOVE: Lobster shacks are as ubiquitous in New England as crab shacks are in the Chesapeake.
/ John M. Chase
Portland Head Light.

Bar Harbor and Mount Desert Island

All sorts of superlatives have been applied to Bar Harbor, the most logical jumping-off point for exploring Acadia National Park. Art galleries, quaint shops and pubs are all over this gracious, entertaining town. Not too far away on the island’s quiet side, Southwest Harbor is home to Maine’s best-known boatbuilders — Ellis Boat Company, Wilbur Yachts and Hinckley Yacht Services, which celebrates its 100th birthday in 2028.

EATING: Step off at Harborside Hotel, Spa & Marina and into Sunrise Cafe or Stewman’s Lobster Pound.

For international flavors try La Bella Vita Ristorante or Paddy’s Irish Pub & Restaurant. Local favorites include Geddy’s Pub, Lompoc Café & Books, the Side Street Café and family-friendly West Street Café. On Main Street are McKay’s Public House, Havana and The Stadium Coffee Shop & Bakery. Find fab food and casual vibes at Bar Harbor Beer Works.

DOCKING: Family-friendly Harborside Hotel, Spa & Marina claims some of the best slips in Bar Harbor. This exquisite resort delivers luxurious accommodations with onsite dining, pool, hot tub and spa. In Southwest Harbor, close to all of its attractions, Dysart’s Great Harbor Marina has dockage for superyachts with a list of amenities that includes a crew lounge, a restaurant and a chandlery. Call on Ellis Boat Company for a mooring.

Stupendous scenery is standard at the summit of Cadillac Mountain within Acadia National Park on Mount Desert Island. © istock.com / James Griffiths Photography

Camden

Snug anchorages, diverse ports, offshore islands and upriver inland attractions combine to make Penobscot Bay one of the world’s best boating areas. If you want to be seen amid Maine’s famous windjammers, Camden is a must-stop. It is upscale, cozy and steeped in tradition.

With an outer harbor that is handsome enough, it is Camden’s inner harbor that shows off the town’s rich nautical and terrestrial architecture. Here, the summer concludes with Labor Day weekend’s Windjammer Festival, which pretty much takes over the port.

EATING: The popular eateries right at Lyman-Morse are Barren’s Distillery & Restaurant, Salt Wharf and the Whistling Whale. In town, begin the day at Bagel Café or Zoot Coffee and stop for lunch at Camden Deli. On Bay View Street is Fresh & Co., the Waterfront Restaurant and Peter Ott’s on the Water. For fine dining visit the Hartstone Inn. Enjoy Long Grain for Asian dishes and 40 Paper for Italian food.

DOCKING: Just across the inner harbor and away from crowds is the new-fashioned and distinguished LymanMorse complex, a top-notch facility with restaurants, onshore crew quarters, fuel, pumpout and laundry.

Boothbay Harbor

Maine’s Midcoast is renowned for its shipbuilding — from the pinnace Virginia in 1607 to the 19th century’s Downeaster and Muscongus Bay and Friendships sloops. You’ll see some replicas alongside bountiful lobster boats in and around Boothbay Harbor, the region’s go-to port. From seaward, Boothbay’s visual appeal is readily apparent, complete with white church steeples and timeless cottages. While it is busy midsummer, the hoopla is toned down a bit in late spring or in autumn.

EATING: Longtime lobster favorites are Boothbay Lobster Wharf and Shannon’s Unshelled. Seafood abounds at Tugboat Inn & Marina and The Whale’s Tale. Locals enjoy Brady’s, Coastal Prime 1901 and family-friendly Kaler’s Restaurant. Also appealing to families is McSeagull’s Restaurant adjacent to Boothbay Harbor Marina.

For pizza cravings visit Pier 1 Pizza and finish the day at Downeast Ice Cream Factory. For breakfast and lunch check out Blue Moon Cafe or Mama D’s Café.

DOCKING: Convenient to downtown and all of its allurements, Boothbay Harbor Marina can handle vessels up to 150 feet LOA and drafts to 16 feet — suitable for the superyachts cruising the region.

Shoreside attractions are well within an easy walk from the waterfront in Camden, the “grande dame” of Penobscot Bay.
© Photo Courtesty of Lyman Morse

Portland

Picturesque skylines grace both sides of Portland Harbor, the commercial hub of the Casco Bay region. Nowhere else on the Maine coast will you find more shoreside entertainment. Be sure to peruse the Old Port neighborhood, the city’s oldest district, an easy walk from just about any of the marinas. Take in some handsome, historic architecture, a multitude of restaurants, various shops and attractions, or just generally enjoy a diverse urban scene.

EATING: The venerable DiMillo’s floating restaurant highlights Maine’s best. Nearby is popular J’s Oyster. Along Commercial Street is Gilbert’s Chowder House, Scales Restaurant, Ri Ra Irish Pub and Flatbread Company.

Fore Street runs parallel to Commercial Street and boasts Fore Street Restaurant, Gritty’s Brew Pub, Central Provisions and Fore Play Sports Pub. Visit Union Restaurant in the Press Hotel for upscale dining. International favorites include Sapporo, Benkay Japanese Restaurant & Sushi Bar, Zen Chinese Bistro, Tandoor, Taco Escobarr and Chaval.

For a great cup o’ joe we recommend Coffee by Design and Bard Coffee. Sweet tooth fixes include Gelato Fiasco, Old Port Candy Company and Beal’s Ice Cream.

In recent years, Portland has become known nationally as a city for food aficionados with its seemingly endless assortment of eateries and bars.

Close to Fore Points Marina are the famous french fries at Duckfat. Near South Port Marine is Taco Trio and Q Street Diner. Next to Sunset Marina is local favorite Saltwater Grille, while patrons of Spring Point Marina will enjoy North 43 Bistro.

DOCKING: Options around the harbor include Fore Points Marina and DiMillo’s Marina alongside downtown and nearby Portland Yacht Services as well as South Port Marine and Spring Point Marina in South Portland.

Steps from the waterfront, Portland’s charming Old Port district brims with funky boutiques and independent restaurants. © istock.com / peeterv

Salem and Beverly

Neighboring Salem and Beverly share a sweeping harbor and lots of history. At one time, they were one, but religious differences in the 17th century caused the two to separate. Known for its Witch Trials in 1692 and overflowing with museums and shops dedicated to the craft, Salem is a hipster haven full of edgy cafés, a rockin’ indie music scene, and much cultural homage to its past.

More laid-back than Salem and less

reliant on tourism, Beverly is where the first Continental navy vessels were based during the Revolutionary War. While the British controlled nearby Boston, the Patriots relied on Salem and Beverly for protection and supply lines. A small blue sign near the foot of the Salem/Beverly Bridge declares Beverly the “Birthplace of Washington’s Navy.”

EATING: Steps from Pickering Wharf Marina is the highly-rated, open-concept Finz. Try Jaho Coffee Roaster, A&J King Artisan Bakers or Gulu-Gulu Café for a quick pick-meup. Near the House of Seven Gables, immortalized in the book of the same

name by Nathaniel Hawthorne, is Mercy Tavern.

On Washington Street are The Derby, Rockafellas, Flying Saucer Pizza Company and Dire Wolf Tavern. Front Street offers the delightful Lobster Shanty. Hawthorne Hotel presents elegant Nathaniel’s and The Tavern, a family-friendly establishment. Cross the bridge to head to Beverly Depot near Beverly Port Marina.

DOCKING: Safe Harbor Hawthorne Cove is the go-to for a slip or mooring. For repairs, call on Fred J. Dion Yacht Yard and Winter Island Yacht Yard, two revered establishments.

Delve into the darker side of Salem’s history at its Witch Museum, a repository dedicated to the city’s infamous past. © istock.com / Kirkikis

Boston Harbor

What began as a simple colonial village set on a grand bay, Boston has grown into a major cosmopolitan center recognized throughout the world. It oozes culture from colleges and universities, restaurants, museums, architecture and theater. There’s convenient public transportation adjacent to the waterfront as well as more than 40 miles of pedestrian- and bikefriendly walkways to explore. The list of things to see and do in “City of Firsts” — consider Boston is the home of America’s first public park, public school and subway system — is endless.

EATING: Head to the Seaport District where the varied options include Cisco Brewers, The Nautilus, Legal Sea Foods, Morton’s The Steakhouse and the casual Tatte Bakery & Café. Waterside dining includes the Barking Crab and James Hook & Co.

For upscale ambiance try Strega Waterfront, Ocean Prime and Del Frisco’s Double Eagle Steakhouse. Find terrific tacos at Bartaco Seaport and tasty treats at Flour Bakery and Café. Visit retro Lucky’s Lounge for late-night fun.

Boston Yacht Haven boaters have the Italian delights of the North End to explore. Anything on the neighborhood’s Hanover Street will be amazing, including Carmelina’s. Boston Waterboat Marina guests can dine at the Chart House. All should explore the many offerings of Faneuil Hall and Quincy Market, which include quick eats, late-night drinks and several favorite, longtime Boston establishments.

Across the Charles River, in walking distance of Charlestown Marina and Constitution Marina, is Pier 6 and the Warren Tavern. Over in East Boston, boaters at Boston Harbor Shipyard & Marina will enjoy local favorite Downeast Cider House.

Boston is one of the most boater-friendly urban destinations in all of America.

DOCKING: Choices are aplenty, as Boston Waterboat Marina sits alongside downtown and the Financial District, nearby Constitution Marina is at the mouth of the Charles River in Charlestown, and Ocean Havens has four facilities encircling all of the inner harbor, including Fan Pier in South Boston, Boston Harbor Shipyard & Marina in East Boston, Charlestown Marina, and Indian Wharf and Boston Yacht Haven downtown. Mystic Marine Fuel is the place to fuel up fast — up to 120 gallons per minute at their high-speed pumps.

Water taxis are a great way for captains and crew to explore the harbor while someone else is at the helm. © Jim Raycroft courtesy of Ocean Havens
Superyachts at Boston Yacht Haven are just a few feet away from the North End neighborhood’s famed Italian restaurants.
© Jim Raycroft courtesy of Ocean Havens

Plymouth

The protected harbor of Plymouth, the oldest continually inhabited English settlement in America, thrives as a fishing community and recreational hotspot. Tourists flock here to learn of the Mayflower’s arrival to the New World in 1620 at the Plimoth Patuxet Museums, a multi-faceted exhibition that should not be missed. It tells

the story of Plymouth Colony and of two cultures, the English and the indigenous Wampanoags, that met in the process, setting the stage for a national Thanksgiving Day.

EATING: Safe Harbor Plymouth offers up Surfside Smokehouse. A short walk away is Italian fine-dining at Cafe Strega. For ultracasual dining at the Town Wharf, try Wood’s Seafood Market & Restaurant and the Lobster

Hut. Just feet from the State Pier is East Bay Grille. Across the street you’ll find The Blue-Eyed Crab Caribbean Grill & Rum Bar and breakfast and lunch options at Portly Pilgrim.

DOCKING: Safe Harbor Plymouth has gas and diesel fuel, pumpout services, a marine store, restaurant and a service yard for all manners of repairs.

Plymouth is where you’ll learn much about the oldest continually inhabited English settlement in America.
© Spiroview Inc / Adobe Stock

events New England

APR PATRIOTS DAY

Boston, Massachusetts

The 130th Boston Marathon takes place on Patriots Day, the third Monday in April, a state holiday that commemorates the battles of Lexington and Concord at the start of the American Revolutionary War.

MAY STRAWBERY BANKE SPRINGFEST

Portsmouth, New Hampshire

Celebrate spring at the Strawbery Banke Museum, where visitors can explore historic landscapes, engage with heritage-breed animals, and learn from expert artisans, gardeners, and farmers from across the region.

ACADIA BIRDING FESTIVAL

Mount Desert, Maine

Atlantic puffins, peregrine falcons, razorbills, arctic terns and other sea and terrestrial birds can be seen on Island walks and boat tours.

JUNE BLOCK ISLAND RACE WEEK

New Shoreham, Rhode Island

Friendly rivalries exist on the water and ashore, and the camaraderie among participants is reminiscent of a reunion of long-lost relatives.

JULY BLESSING OF THE FLEET

Galilee, Rhode Island

Commercial and recreational boats dress up for a parade and there is a ceremonial blessing by local clergy. The event also includes lots of food and live music plus a 10-mile run, which could be comical for those with sea legs.

SAIL250 ®

Boston, Massachusetts

The last destination for the Sail250® international fleet of the world’s most magnificent tall ships and military vessels makes its way into Boston in mid-July.

AUG FEAST OF THE BLESSED SACRAMENT

New Bedford, Massachusetts

Founded in 1915 and predicated on the religious festivals common in Europe, this four-day event is one of the world’s largest Portuguese celebrations, and includes parades, a carnival, road race, live music and lots of delicious food and drink.

SEPT OPEN LIGHTHOUSE DAY

Maine

The general public gets the rare opportunity to visit more than a dozen Maine lights. Sponsored by the American Lighthouse Foundation, the United States Coast Guard and the Maine Office of Tourism, it’s a perfect family activity that combines history, coastal exploration, and hands-on learning.

OCT HAUNTED HAPPENINGS

Salem, Massachusetts

For the entire month of October, the Mecca of Halloween is the site of a grand parade, costume balls, ghost tours, haunted houses, live music, chilling theatrical presentations and other family-friendly events.

NOV WATERFIRE SALUTE TO VETERANS

Providence, Rhode Island

Veterans and active duty military hold torches as they march into the Waterplace Park Basin to create a Ring of Fire during the lighting of the braziers. Speeches and tributes make it a moving experience for all.

Provincetown

With its harbor cradled in a rolling, sandy fist of land, Provincetown has always protected its arrivals. Whalers, Portuguese fishermen and pirates came by sea. Artists, writers, entertainers, politicians, family vacationers and the LGBTQ community continue to come by land. All were and are welcomed by Provincetown. The result is a modern medley of people and places that make the historic district a fascinating and fun central hub.

EATING: Fanizzi’s and Ciro & Sal’s each serve up delicious Italian entrées. Dine elegantly at the Pointe Tavern in the Crowne Point Hotel & Spa. Commercial Street hosts Bubala’s by the Bay, Café Heaven and the Provincetown Portuguese Bakery. Don’t miss the neon lights of The Lobster Pot.

The Red Inn diners enjoy views of the Long Point Light Station. Find beachfront dining at The Mews Restaurant & Café. For a morning

wake-up, stroll Commercial Street, as there are numerous coffee shops within easy walking distance of the town’s MacMillan Pier.

DOCKING: Provincetown Marina is especially suited to accommodate superyachts up to 250 feet LOA. Their captain’s lounge area and fire pits are great for socializing with new friends.

Hyannis

Thanks to the notoriety the village has gotten from its most famous residents — the Kennedys — Hyannis is now of one of New England’s biggest tourist and boating destinations. It is absolutely jam-packed with restaurants, nightclubs, shops and people. Cape Cod’s largest year-round population resides in Hyannis, and many others travel to this hub for commercial and professional services not found elsewhere. Most everything is an easy jaunt from the marinas.

EATING: Hyannis Marina has two choices, Trader Ed’s Cabana Bar and family-friendly Tugboats with great outdoor dining. West of the ferries is Baxter’s Boathouse — use VHF 71 for boat parking. Opposite Bismore Park Marina is the Black Cat Tavern.

On Main Street you’ll find Alberto’s Ristorante, emBargo for tapas, Colombo’s Café & Pastries, Tumi Ceviche Bar & Ristorante and the Brazilian Grill.

DOCKING: You’ll find two restaurants, a pool, cabana bar, gift shop, discount store and extensive parts department at Hyannis Marina, which boasts deep water for vessels up to 200 feet.

A ferry heads to its berth within Hyannis’ Inner Harbor. Transient-welcoming Hyannis Marina is the large facility on the opposite side of the port.
© Shoreline Aerial Photography
Practitioners in prayer pose during yoga alongside Provincetown Harbor.
© Photo Courtesy of Ocean Havens

Nantucket

The very definition of a New England seaport, Nantucket is one of the crown jewels of the boating community, drawing a coterie of sophisticated and cerebral sailors. Its cobblestone streets are lined with cedar-shingled buildings and brim with history. The island’s flat terrain makes it easy to pedal and walk around, and there are more than 35 miles of paved paths for bikes and pedestrians. You could while away a full day browsing the myriad boutiques, art galleries and museums here.

EATING: Everything is near or at the harbor, and reservations are recommended. At Nantucket Boat Basin, try Slip 14 or head to Straight Wharf Restaurant. The family-friendly Nantucket Lobster Trap is nearby on Washington Street. Also check out The Nautilus for tapas and The Club Car to dine in an actual train car. The Brotherhood of Thieves is where locals hang out.

Whether or not you think 26 miles offshore is far, Nantucket indisputably takes you away from it all.

DOCKING: Nantucket Boat Basin is ideally situated right in the heart of town. This premiere facility’s full-range of services includes a concierge, who will help you with just about anything you need.

Dinghies diddle comfortably within the Easy Street basin between Nantucket’s Old North Wharf, right, and Steamboat Wharf.
© Photo courtesy of Nantucket Boat Basin

Martha’s Vineyard

Boaters have four distinct harbors to choose from on Martha’s Vineyard, an idyllic island just 7 miles off the coast of Massachusetts. Boats from small classics to superyachts ply the waters here. Choose your desired ambience from the fishing village vibe of Menemsha, the yachting aura of Edgartown, the gingerbread houselined streets of Oak Bluffs or the bustling Vineyard Haven entryway with its “Black Dog” legacy. No matter your taste, you’ll find a way to appease it here.

EATING: You can munch with a harbor view in Oak Bluffs. Nancy’s Restaurant serves casual seafood. Next door, Lobsterville Bar & Grille

shows off great sunsets on its open-air deck. Also at the harbor, the Coop de Ville Restaurant is a fun ride, while Lookout Tavern is known for its lobster roll.

In Edgartown, you’ll find dining options not far from the waterfront. L’Etoile on North Water Street is located in a whaling captain’s house. For Italian, try the popular Chesca’s, and for family fun visit The Seafood Shanty. In Vineyard Haven, La Soffitta and Salvatore’s are highly-rated Italian delights, while Garde East has an often-changing, inviting menu.

DOCKING: Vineyard Haven Marina and Safe Harbor Vineyard Haven have slips and moorings within the island’s preeminent port. Oak Bluffs Marina has slips and moorings. An alternative to the east in Edgartown Harbor is Mad Max Marina.

To a great many cruisers along the East Coast, Martha’s Vineyard is the primary destination for a summer’s sail.
Oak Bluff’s side-by-side gingerbread cottages with their ornamental facades grab one’s attention on Martha’s Vineyard. © istock.com / Bonnie Donovan

Pocasset and Red Brook Harbors

Located about 50 miles from Block Island and 20 miles from Martha’s Vineyard, Pocasset and Red Brook harbors offer some of the best natural protection in Buzzards Bay. Some boaters duck in here while waiting to transit the nearby Cape Cod Canal; others are looking for respite from the prevailing summer southwesterlies. Most, though, come to enjoy the area and visit the small but charming villages that are part of the town of Bourne.

EATING: The seasonal Chart Room at Kingman Yacht Center is a great dockside choice. This the top place to swap stories with fellow cruisers.

Inland you’ll enjoy the lively atmosphere of the Courtyard Restaurant & Bar and the family- and pet-friendly Local Grounds Coffee House & Café for breakfast and lunch. From Barlow’s Landing in Pocasset Harbor, you’ll have access to Graziella’s Pizzeria.

DOCKING: Both Kingman Yacht Center and Parker’s Boat Yard have slips and moorings, dinghy docks, launch services, haulouts, repairs, and gas and diesel fuel.

Grab a slip or mooring from Kingman’s or Parker’s in Pocasset and Red Brook, then grab a cocktail and watch the sunset.
© Photo courtesy of Kingman Yacht Center

New Bedford and Fairhaven

Its reputation not as glamorous as Newport, Nantucket and the like, New Bedford is often overlooked. The harbor, which includes the neighboring town of Fairhaven, was once the world’s whaling capital; today, it’s the highest earning of America’s fishing ports.

Ashore, there’s a lot for a visitor to do, with plenty of historic sites, amusing attractions, a vibrant arts scene and

fabulous dining. Walking is easy, as most of the attractions are within a few blocks of the waterfront.

EATING: In New Bedford, dock and dine at Cisco Brewers Kitchen & Bar. The downtown waterfront has the seafood shack, The Whale’s Tail, and its upscale sister, The Black Whale. Grab a pick-me-up at neighboring Mirasol’s Café. Just south is Merrill’s on the Waterfront and its view of the country’s most active fishing port. It’s just a few strides inland to the National Club, a Mexican cantina, and the Candela Cucina, an upscale Italian restaurant.

On Pope’s Island, Fathoms Bar & Grille has dockage for diners. At Seaport Resort & Marina in Fairhaven, start the day at Saffron Café & Pastry and end it with the authentic Indian flavors of Saffron by the Sea.

DOCKING: Managed by the New Bedford Port Authority and always garnering praise from its guests, Pope’s Island Marina has free pumpout, a picnic area, a playground, and plenty of space to walk the pooch. A scene to be seen, Cisco Brewers Kitchen & Bar at the harbor’s entrance has a dock and moorings for patrons.

A casual venue on New Bedford’s working waterfront, The Whale’s Tail is an old school, top-notch seafood shack. © Photo courtesy of Servedwell Hospitality
The atmosphere, the booze, the food and the music draw many to the waterfront Cisco Brewers Kitchen & Bar in New Bedford.
© Photo courtesy of Servedwell Hospitality

Newport

You could spend an entire summer trying to see the sites in Newport — the town is a smorgasbord of delights. There’s plenty for everyone, no matter your interest or your budget.

Downtown is small and packed with shops and restaurants. A little farther afield there are the mansions of a bygone era on Bellevue Avenue and Ocean Drive. Other favorite points of interest include the Cliff Walk, the International Tennis Hall of Fame, the National Sailing Hall of Fame, Fort Adams State Park, the Touro Synagogue, the Newport Naval Station and much, much more. For the inside scoop, visit the Discover Newport Visitor Information Center, just a few blocks north of Bowen’s Wharf.

EATING: Upscale dining is on the table at The White Horse Tavern, the oldest continuously run tavern in the New World. Be sure to explore Thames Street’s bountiful bars and restaurants, including the Newport Blues Café and One Pelham East.

At Safe Harbor Newport Shipyard, grab breakfast or lunch at Belle’s Café. At Oldport Marine, try the barbecue goodness of Smoke House or the seafood at The Mooring. Nearby is Bannister’s Wharf where you can dine in style at The Clarke Cooke House or The Black Pearl.

Bowen’s Wharf is a smorgasbord with Luke’s Lobster, 22 Bowen’s Wine Bar & Grille, Diego’s, Wharf Southern Kitchen & Whiskey Bar, The Landing and the Wharf Fish House & Tiki Bar. Enjoy great views and eats from

Saltwater at The Newport Harbor Hotel & Marina.

Forty 1 Degrees North offers several dining venues, and Waite’s Wharf has At The Deck and O’Brien’s Pub. Across the bridge, Goat Island Marina presents lunch, dinner and drinks at Marina Café & Pub.

DOCKING: There’s a wide variety of options to the visiting boater with the convenience of being in or near downtown. These include Goat Island Marina, Safe Harbor Newport Shipyard, The Newport Harbor Hotel & Marina, the Newport Maritime Center, Brown & Howard Marina and the Newport Marina at Lee’s Wharf.

Classic and classy yachts share the harbor here, especially during the annual Newport International Boat Show in September.
© Photo courtesy of Newport International Boat Show

New England

Attractions

WOODENBOAT SCHOOL

Brooklin, Maine

WINDJAMMER FESTIVALS

Boothbay and Camden, Maine

YANKEE HOMECOMING

Newburyport, Massachusetts

HAMMOND CASTLE MUSEUM

Gloucester, Massachusetts

ADAMS NATIONAL PARK

Quincy, Massachusetts

MONOMOY ISLAND NATIONAL WILDLIFE REFUGE

Chatham, Massachusetts

SHINING SEA BIKEWAY

Falmouth, Massachusetts

AQUINNAH CLIFFS

Menemsha, Massachusetts

BATTLESHIP COVE MUSEUM

Fall River, Massachusetts

GREEN ANIMALS TOPIARY GARDEN

Portsmouth, Rhode Island

BLITHEWOLD MANSION, GARDENS & ARBORETUM

Bristol, Rhode Island

Hyannis Harbor Lighthouse on Cape Cod.

Block Island

All types of yacht racers, fishermen, bicyclists, bird watchers, beach lovers, environmentalists and partygoers from around the globe converge on Block Island, a premier port of refuge for anyone on an Atlantic Ocean voyage. Despite its popularity, Block Island has managed to retain a faraway feeling.

The windswept landscape reminds one of Scotland or Wales with its rolling hills and rugged ravines. Mansard and gambrel roofs cover lovely gingerbread and Victorian homes. Miles of Colonial-era stone walls, hundreds of freshwater ponds and amusements mostly of the oldfashioned variety evoke an earlier era. If it weren’t for the buzz, beep, bing, ding and ring of the electronic devices in everyone’s hands, you’d swear you were in a time warp here.

EATING: Great Salt Pond offers many dining options. Champlin’s Marina & Resort serves up New England favorites at The Landing, cocktails

at Trader’s Dock Bar and at Tiki at the Top, Mexican dishes at Blockamole, and grab-and-go options at Café Boutique.

At New Harbor Boat Basin, The Oar serves lunch and dinner. Payne’s Dock offers dining at LobsterCraft and nearby is the always-buzzing Dead Eye Dick’s.

You’ll find great dining with a great view at Ballard’s Beach Resort in Old Harbor, right next to the ferry dock. Restaurants that are within crawling distance of the waterfront include Poor People’s Pub, Winfield’s and the familyfriendly McAloons. A favorite among boaters is the Italian staple, Aldo’s, and its sibling, Aldo’s Bakery & Homemade Ice Cream. For a late-night buzz check out Yellow Kittens. In the morning, grab breakfast at Persephone’s Kitchen.

DOCKING: Champlin’s Marina & Resort and Payne’s Dock have groceries, bike and moped rentals, and restaurants on-site or close by. They’re also the only places to get gas and diesel fuel on the island.

Block Island is a hilly terrain of impressive cliffs, giant ravines, spectacular beaches, country farms, 200 miles of Colonialera stone walls, and 300 freshwater ponds. Nature is the major attraction here.
With all of its amenities and space for superyachts, Champlin’s Resort is its own major attraction in Great Salt Pond.
© Aram Boghosian, courtesty of TPG Marinas

New York Harbor frames the Statue of Liberty, a timeless symbol of freedom, welcoming ships, immigrants, and dreamers with open arms against a glittering skyline.

Long Island Sound

A sea of city shoresides and calm coves

Roughly 100 miles long from New York’s Throgs Neck to Watch Hill, Rhode Island, with an average width of 15 miles, the Sound is almost entirely enclosed by Long Island to the south and the Connecticut mainland to the north. Add New York City, which identifies as being part of the region, and neighboring New Jersey, and you’re talking around 30 million people residing near the Sound. Even with all of these people, the Sound offers boaters a fascinating variety of courses and destinations that let you escape the hurly-burly of daily living.

There are more than 60 ports for a boater to call on within this region. Start with the Big Apple, the City That Never Sleeps — New York. Firsttimers find the harbor’s navigation nerve-wracking but endless rewards wait ashore.

Beyond the city proper are the varied harbors of Westchester County and Western Connecticut on the Sound’s north side. From these relatively affluent ports, you have a wealth

of shoreside attractions alongside high-end marinas with top-notch maintenance crews and easy access to supplies.

As you move up the Central and Eastern Connecticut coasts the influence of New York City starts to fade as the rural feel of New England begins to take form. Tranquil yet vibrant communities dot the shoreline from New Haven to Stonington. It’s even more easy going in Western Rhode Island.

Across the Sound, the dual forks of Eastern Long Island have inviting bays, deep harbors and plenty of protected water to roam. Ashore, New Yorkers may brag that it’s the world’s best wine country.

Western Long Island, aka the North Shore, puts you back into Manhattan’s orbit with lively harbors packed full of vessels ranging from sunfish to superyachts. The same can be said for New Jersey, which — along with Connecticut — completes the phrase “Tri-State Area” that you’ll hear a lot.

Two Nordic Tugs enter New York Harbor past the Statue of Liberty.
© Photo courtesy of Paul Tortora, Wilde Yacht Sales LLC

Greenport and Southold

The charming maritime village of Greenport certainly deserves its excellent reputation as one of the friendliest ports of call along the Eastern Seaboard. Jam-packed with intriguing and entertaining seaside shops and restaurants, this former whaling and shipbuilding port features plenty of conveniences, most just a short five-minute walk from your marina.

Founded in 1640 by Puritans from the New Haven Colony, Southold is more spread out and suburban than its neighbor to the east. Its downtown may lack the overwhelming nautical flavor of Greenport, but Southold, too, is a pleasant place to visit.

EATING: There are around two dozen places to dine within a half-mile or so from the marinas. Any restaurant you try within the village area is a solid choice. The mainstay here

is Claudio’s, which originally opened in 1870. Fortino’s Tavern has dining over the water, Alpina features Swiss and Italian fare, Anker is modeled after a sailboat with fare way better than most galleys, and Porto Bello Restaurant at Safe Harbor Stirling is the go-to for Northern Italian fare.

Don’t forget the wine! More than 40 vineyards are in this region known as the North Fork. Live bands, art exhibitions and some great food are often paired with the tastings here. For a guided adventure, try North Fork Wine Tours, which is based in Greenport, right at Townsend Manor Marina.

DOCKING: Townsend Manor Marina, the village-run Mitchell Park Marina and the two Safe Harbor marinas are top-notch choices in Greenport. The institution here is Preston’s Chandlery, which has been in the same building since 1880 when it was founded by Boston sea captain Samuel Truman Preston. They often have a few slips here for visiting boaters.

An established, renowned wine region, the North Fork has a cool, ocean climate that is similar to Bordeaux, France. © istock.com / xavierarnau

Sag Harbor

Astute boaters will notice the opulence of Sag Harbor long before making fast their dock lines. It is the summer hometown for a marquee list of authors, artists and musicians who live quietly among the many small-business owners and longtime residents. Visit on a summer weekend and you’ll find this place alive and rocking. Stay over during midweek or slightly off-season and it is more likely to strike you as charming and relaxing.

EATING: Sophisticated spots for a date night are The American Hotel and LuLu Kitchen & Bar. Head to Sen for Japanese, Il Capuccino Ristorante for Northern Italian and K Pasa for California cuisine. The Corner Bar is the local watering hole with moderately priced fare.

DOCKING: Sag Harbor Yacht Yard is within easy walking distance to the village’s best shops and restaurants. Ship Ashore Marina also has transient slips and can handle all manner of repairs.

Port Jefferson

With plenty of deep-water access, an easy approach and high bluffs to buffer the wind, Port Jefferson is a great place to spend with fellow boaters. And, you’ll never run out of things to do here. The village absolutely pulses with life, and its restaurants, boutiques, galleries, night life and interesting places to visit are mostly found within an easy walk of the marinas. This popular destination, which was named after President Thomas Jefferson in 1836, has plenty of activities to suit all ages.

EATING: At Danfords Hotel, Marina & Spa, you’ll find Ferryman’s Grille. Get seafood across the street at the Steam Room. Prohibition Port Jefferson, Salsa Salsa and Pasta Pasta are neat places with clever names and menus. So, too is Torte Jeff Pie Co., a must for donuts. Grab coffee at Local’s Café.

DOCKING: Top-shelf Danfords Hotel, Marina & Spa and the Port Jefferson Town Marina.

A stroll down Sag Harbor’s inviting Main Street provides a persistent sense of elegance and worldliness. © istock.com / Pgiam

Mystic

One of the Nutmeg State’s most beloved destinations, Mystic is history — living history. The world-famous Mystic Seaport Museum and the Mystic Aquarium bring the wonders of sailing and the sea to millions of people every year. The homes in and around town breathe history along streets lined with interesting boutiques, antique shops, galleries and restaurants. It is a lot of fun to just walk around, window shop, and look at the old ship captains’ houses.

EATING: The 18th century New England ambiance of The Captain Daniel Packer Inne has long made it a local favorite. Bank & Bridge Brewing, The Mariner and The Oyster Club are also popular. Mystic Pizza has been around for more than 50 years, having inspired a movie of the same name in 1988. Pop Over Eatery is tops for breakfast and lunch. Get a scoop or three at the Mystic Drawbridge Ice Cream Café.

DOCKING: First upriver is Noank Village Boatyard, then there’s Mystic River Marina, Mystic Shipyard, Fort Rachel Marina and the Mystic Seaport Museum Marina, an ideal place to stay while visiting the Seaport.

Settled by the English in 1645 and named after a Pequot word for tidal river, Mystic breathes history. The timeless lure of the sea clocks to a stop here.
The whaling ship Charles W. Morgan spotlights Mystic Seaport Museum, a re-creation of a 19th century seafaring village.
© Kristine Rothaupt

events Long Island Sound

APR CHERRY BLOSSOM FESTIVAL

New Haven, Connecticut

Wooster Square Park has more than 70 Yoshino cherry trees, which were first planted more than 50 years ago. It’s a stunning display and probably the state’s largest collection.

MAY MUBADALA SAIL GRAND PRIX

New York Harbor

Identical hydrofoiling, F50 catamarans race at 60 mph speeds around the Upper Harbor between the base camp at Liberty Landing and the operations center at Governors Island on the month’s last weekend.

EXIT ZERO JAZZ FESTIVAL

Cape May, New Jersey

Performances by headlining legends and up-and-comers alike take place at several venues over a three-day weekend mid-month.

JUNE CONEY ISLAND MERMAID PARADE

Brooklyn, New York

Participants in handmade costumes based on the year’s theme — no ethnic, religious or commercial aims — saunter sunnily in the nation’s largest art parade. Takes place on the third Saturday.

HARBORFEST

Port Washington, New York

This Chamber of Commerce spectacle in early June at the North Hempstead Town Dock features nautical exhibits, a model boat regatta, music, crafts and plenty of family fun.

JULY AROUND LONG ISLAND REGATTA

Sea Cliff Yacht Club, Hempstead Harbor, New York

Open to all sailboats 24 feet and up, this 207-mile, late-July race begins at the Statue of Liberty then circumnavigates the largest and longest island in the contiguous United States.

LARCHMONT RACE WEEK

Larchmont, New York

Just about every summer since 1885 the prestigious Larchmont Yacht Club has hosted Race Week. It’s highquality racing with a lot of camaraderie and partying over eight days.

AUG POTATO AND CORN FESTIVAL

North Branford, Connecticut

Family fun at its finest: Potato sack races, corn husking contest, carnival rides, pie-eating contest, petting zoo, car show and hula hoop contest among the merriment.

SEPT OYSTER FESTIVAL

Norwalk, Connecticut

Everything from dogs doing acrobatics to a Bunyan-esque lumberjack competition have occurred at this September celebration promoting coastal cuisine, accompanied by concerts and carnival rides.

FERRAGOSTO FESTIVAL

Little Italy, Bronx, New York

An early September commemoration of the neighborhood’s rich culture with traditional Italian food and abundant entertainment.

Old Saybrook

At the Connecticut River’s mouth, Old Saybrook is teeming with marine facilities alongside beautiful coves. Ashore you’ll find small shopping malls as well as some unique Main Street shops, neighborhoods lined with large and architecturally high-quality houses, and a cultural arts center named after the town’s legendary resident Katharine Hepburn. Her former home in the Borough of Fenwick sits amongst some of Connecticut’s most beautiful properties overlooking Long Island Sound.

EATING: Upscale Fresh Salt at Saybrook Point Marina, Liv’s Shack at Harbor One Marina and La Marea at Safe Harbor are great places to meet fellow boaters. Johnny Ad’s, Jack Rabbits and the Penny Lane Pub are casual spots. The Tea Kettle is a must for breakfast and Sweet Luna’s is the go-to for dessert.

DOCKING: Get a slip and be spoiled at Saybrook Point Resort & Marina, where its wide-ranging amenities could keep you around for a good, long stretch.

A post-card perfect, classic town with idyllic shorelines, Old Saybrook is packed with thriving small shops, diverse dining and first-rate marinas deserving discovery.
Saybrook Point Resort & Marina is one of the favorite stopovers for boaters cruising the Sound between Newport and New York.
© Photo courtesy of Saybrook Point Resort & Marina

Essex

The praises and superlatives applied to Essex entice tourists, transplant residents and boaters — primarily because they are more than warranted. The mix of attributes is dreamy: a field of classic sailboats moored in the harbor like a living photograph; a 1776 inn where sea chanteys sway the tap room; two parks alive with activity (one, the waterfront grounds of a river museum housed in an 1878 steamboat warehouse), restored captains’ homes, and elegant shops lining Main Street toward the harbor.

EATING: Follow the locals to the Black Seal, The Griswold Inn and Privateers Pizza & Provisions. On the water, there’s Dockside Seafood & Grill, the Siren Kitchen & Bar and Noah’s at 63 Main. Grab a sandwich at Olive Oyl’s and get stuff for your larder at Cooked Marketplace. Caffeine and desserts are at Essex Coffee & Tea Company and the adjacent Sweet P’s.

DOCKING: Essex Boat Works is the landmark here and Safe Harbor has three facilities encompassing the harbor.

Maintaining a great deal of its maritime heritage, Essex is known today as a yachting capital, comparable in all respects, except size, to Newport and Annapolis.
A yachtsman’s refuge known by regulars as “The Gris,” the Griswold Inn has been in operation since 1776. © Joe Mabel

Norwalk

Norwalk Harbor has a comprehensive marine facility at its mouth near beaches, a world-class aquarium on the western shore, and a fair share of dock and dines. Be sure to peruse the rejuvenated neighborhood of SoNo, where the streets are lined by diverse restaurants, brewpubs, art galleries, antique shops, bookstores and boutiques. The Maritime Aquarium at Norwalk here is housed in a pair of restored iron foundries and is home to 75 live exhibits featuring more than 7,000 animals and many focusing on Long Island Sound.

EATING: At Norwalk Cove Marina, hit the Galley Waterfront Café for delightful breakfast and lunch sandwiches and the seafood-centric Sunset Grille for dinner. Satisfy your Italian craving at Valentino’s Cucina Italiano, while Tablao Wine Bar & Restaurant is a cozy spot for a taste of Spain. Dock-and-dines include SoNo Seaport Seafood and Harbor Lights.

DOCKING: Norwalk Cove Marina and Rex Marine Center.

New York City

Come ashore on Manhattan, and you’re treated to a 24-hour smorgasbord. You’ll find no other place like this in the world. For you to hit every item on your must-do list, you would have to forgo sleep, which is perfect in “The City That Never Sleeps!” Our advice is to ingest it in small bites.

Naturally, you’ll want to visit some of the best-known landmarks. Statue Cruises runs to the Statue of Liberty and Ellis Island from Manhattan’s Battery Park and New Jersey’s Liberty State Park, which is adjacent to Liberty Landing Marina. Very close to North Cove Marina are Wall Street and the National September 11

Memorial & Museum. Uptown in Midtown you have the Empire State Building, Rockefeller Center, the Theater District and Times Square. The USS Intrepid Sea, Air and Space Museum Complex is to the west on the Hudson River.

A little farther north is Central Park, Lincoln Center, the Metropolitan Museum of Art and the American Museum of Natural History. On the Upper West Side is Riverside Park, which stretches for 4 miles and is home to 79th Street Boat Basin. Dyckman Marina, at the northwestern tip of Manhattan, abuts Fort Tryon Park, home to The Cloisters, which is governed by the Metropolitan Museum of Art.

EATING: Choosing a place to wine and dine may give you optionparalysis. There are entire books and websites devoted to the everchanging dining scene here. Half the fun of a New York City visit is the discovery — no matter how many times you’ve been here, you’ll always

If you can steer a boat, you can easily navigate New York City, either on your own or on a tour.

find something new, especially at mealtime. Go with your gut, and be sure to ask your dockmaster and marina mates for their favorites.

DOCKING: Liberty Landing on the New Jersey side of the Hudson River has great views of Lower Manhattan and a ferry to it. On the Manhattan side, Chelsea Piers Marina abuts a 4-mile, 550-acre greenway with bike and walking paths, playgrounds and dog runs.

Urban planners around the world envy the aerial greenway known as The High Line, a redeveloped freight line along Manhattan’s West Side where you can stroll above the streets below. © istock.com / ferrantraite

Cape May

The southernmost reach of the Jersey shore truly pleases everyone: it’s a fisherman’s heaven, a romantic getaway for couples, and the ideal place for a family vacation. The town’s relaxed atmosphere is perfect for anyone looking for a bit of R-and-R. Play some mini-golf, catch a movie on the beach, poke around at the shops, sun yourself, or just take a stroll and admire the architecture, especially the big, Victorian porches that bring yesteryear into crisp focus. There’s also a trolley tour of this historic, seaside resort.

EATING: The Lobster House, adjacent to Utsch’s Marina, is a mainstay and South Jersey Marina has a restaurant on site. Upscale, fine dining may be had beachside at Union Park Dining Room or Peter Shields Inn. In town, the Washington Inn and the Blue Fish Inn have solid reputations. Visit Uncle Bill’s Pancake House or the Mad Batter for breakfast.

DOCKING: Utsch’s Marina and South Jersey Marina have slips, fuel, marine supplies, laundry facilities and much, much more.

Handsome architecture adorns Cape May’s streets, which are easy to bike or stroll. © istock.com / benedek
Beat a path to Cape May, a convenient, safe stopover to await weather or tides — and a fascinating place to visit on its own. © istock.com / Kirkikis

Attractions Long Island Sound

ANCIENT MUSTER

Deep River, Connecticut

BARNUM FESTIVAL

Bridgeport, Connecticut

CRUISE NIGHT

Oyster Bay, New York

FLYING HORSE CAROUSEL

Watch Hill, Rhode Island

HAMPTON CLASSIC HORSE SHOW

Bridgehampton, New York

MARK TWAIN HOUSE & MUSEUM

Hartford, Connecticut

MONTAUK POINT

LIGHTHOUSE MUSEUM

Montauk, New York

SHINNECOCK POWWOW

Southampton, New York

SHORE LINE TROLLEY MUSEUM

Branford, Connecticut

WALT WHITMAN BIRTHPLACE

Huntington Station, New York

Long Island Sound

Paul Tortora, Wilde Yacht Sales LLC

The Chesapeake Bay is the nation’s largest estuary, with a combination of fresh and salt water that has provided centuries of copious cruising and bountiful harvests of shellfish for many groups and cultures.

Chesapeake

The Bay is an explorer’s promised land

You could spend a lifetime on the Chesapeake and its tributaries and still not see every worthwhile gunkhole. The largest inlet in the Atlantic Coastal Plain of the eastern United States, the Chesapeake Bay is nearly 200 miles long and 3 to 25 miles wide. The northern part is bordered by Maryland and its southern part by Virginia.

The Upper Chesapeake Bay’s eastern shore is a lush oasis with small towns and farmland defining much of its character. Drink in the loveliness of the green banks with miles of rolling hills and tall trees decorating the waterside bluffs until you reach the Chester River, where the topography flattens out to become a sandy, alluvial plain. Much of the Eastern Shore is blessed with relative peace — pastoral is a good word for it.

The birthplace of America’s national anthem, Baltimore is the hub of the Upper Chesapeake Bay’s western shore and has much to offer. It is a major city with appealing sights, sounds, restaurants and activities.

Other premier ports of call in the region include Annapolis, Maryland’s capital and the home of the U.S. Naval Academy, and Solomons Island, the site of America’s first naval amphibious training base. To the south, the Potomac River offers beautiful scenery and, of course, it’s the only way by water to Washington, D.C., the capitol of the nation that turns 250 in 2026.

Virginia is where Capt. John Smith sailed into Chesapeake Bay and decided that this would be a good place to establish the first colonial settlement in 1607. He was also the first English explorer to map the Chesapeake Bay area.

Nowhere is the power of the nation and Virginia’s seafaring tradition more evident that at the Newport News shipyards and the Norfolk Naval Station, home to the world’s largest collection of warships. Conversely, Virginia’s Eastern Shore waters and towns are steadfastly oriented to the Bay’s natural riches, a place where you can still get away from it all.

ABOVE: Fishing near the Bay Bridge.
© Photo courtesy of Jay Fleming
LEFT: Forty screw-pile lighthouses were built on the Bay between 1850 and 1900.
Only Thomas Point Shoal Light near Annapolis remains at its original site.
© Photo courtesy of Jay Fleming

Baltimore

For urban bustle, shopping and entertainment, make a trip up the Patapsco River to Baltimore, Maryland’s most historic and biggest attraction. Its harbor is the very birthplace of the U.S. national anthem — a buoy marks the spot where Francis Scott Key penned the words to “The Star-Spangled Banner.”

You’ll find a wealth of museums, restaurants, jazz clubs, galleries and much more are all within walking distance of the many marinas in the harbor. Indeed, there is so much to do here, whether with a family or on your own, that even with a week to kill you’ll barely make a dent.

EATING: All of the large marinas here have dining opportunities just steps from your slip. In Fells Point,

Slainte Irish Pub is where soccer fans religiously congregate. Neighboring favorites include Kooper’s Tavern for American dishes and the Rec Pier Chop House for classic Italian. Thames Street Oyster House tops many “best of” lists and Duda’s Tavern is legendary.

To the west toward the Inner Harbor the Italian standbys are Amicci’s, Café Gia and Sabatino’s. To the south in Federal Hill, just wander or ask your marina for their gotos. The Cross Street Market is a must for provisioning.

DOCKING: Lighthouse Point Marina and Henderson’s Wharf in Northwest Harbor, Harbor East and the Inner Harbor Marina near downtown’s attractions, and Port Covington Marina on the port’s southwest side.

Those who like to keep a busy schedule will absolutely love Baltimore and its abundant opportunities for the inquisitive. © istock.com / Pgiam

Attractions Chesapeake

FORT DELAWARE

Delaware City, Delaware

RAILWAY MUSEUM

Chesapeake Beach, Maryland

CALVERT MARINE MUSEUM

Solomons Island, Maryland

PATUXENT RIVER NAVAL AIR MUSEUM

Lexington Park, Maryland

FISHERMEN’S MUSEUM

Reedville, Virginia

DELTAVILLE MARITIME MUSEUM

Deltaville, Virginia

STEAMBOAT ERA MUSEUM

Irvington, Virginia

GREAT BRIDGE BATTLEFIELD & WATERWAYS MUSEUM

Chesapeake, Virginia

BLACK HISTORY TOUR

Hampton, Virginia

BOARDWALK

Virginia Beach, Virginia

© Joy McPeters

St. Michaels

An intimate little harbor with a surprising number of amenities gracefully contained within, St. Michaels is one of the Chesapeake Bay’s great boating hubs. It also has lots to offer the nonboating public, to judge by the weekend crowds. Yet despite its popularity, St. Michaels manages to retain its smalltown feel. It features a comfortable mix of city-sophisticated and countryfriendly atmospheres, reflected in the bend of upscale shops, worldclass restaurants and local watering holes that welcome you as though you’ve been here for

a lifetime. (Be sure to spend time at the Chesapeake Bay Maritime Museum, an 18-acre waterfront complex.)

EATING: The long-running Blu Miles Seafood & Grill Restaurant, housed in an 1830s oyster-shucking shed, and the island-inspired Foxy’s Harbor Grille attract many to St. Michaels Marina. Carpenter Street Saloon and Eastern Shore Brewing are the places to swap sailing stories among likeminded folks. Wine and dine favorites enjoyed by locals and visitors alike include the Bistro, Theo’s, Ava’s and the St. Michaels winery.

DOCKING: In the center of the waterfront, the St. Michaels Marina overflows with excellent services and amenities for visiting boaters.

The 1879 Hooper’s Straight screwpile lighthouse bedecks the already-enriching Chesapeake Bay Maritime Museum in St. Michaels.
© Photo courtesy of Jay Fleming

Annapolis

Sophisticated-yet-casual Annapolis is about as boatercentric a place as you will find, sitting amongst the prestige of the United States Naval Academy. It is a fun-loving, walkable town with easy shoreside access, a fascinating history, intimate shops, numerous fairs and events, plus some really terrific eateries.

Settled in the mid-1600s and incorporated in 1796, Annapolis breathes history and charm with cobblestoned main streets and tree-lined brick sidewalks. Perhaps the most famous of the city’s landmarks is the Maryland State House, completed in 1779, the oldest capital building in continuous service in the nation.

The one attraction that is a must-see is the U.S. Naval Academy. If you need help finding it, just ask one of the many uniformed cadets walking about town. An obvious landmark from the water is the 2,500-seat Academy

Chapel. Nearby Bancroft Hall, overlooking the Severn River, is the largest dormitory in the country.

EATING: Around almost every corner of downtown Annapolis lies a dining and drinking establishment. Pub crawls are popular, as you could easily stumble from one bar to the next. We suggest eating first at the Iron Rooster, the Middleton Tavern or McGarvey’s, all near the City Dock. Galway Bay Irish Restaurant & Pub is a quartermile inland. Head up Main Street for Chick & Ruth’s Delly, Osteria 177, the Preserve and Café Normandie.

On the opposite side of the harbor in Eastport, grab a seat among fellow sailors at the Boatyard Bar & Grill or Lewnes’ Steakhouse. Spoil your date at Ruth’s Chris and Chart House Prime. The ultimate comfort food is found at Bread & Butter Kitchen, which is open for breakfast and lunch.

DOCKING: Among the myriad options are Port Annapolis Marina, Bert Jabin Yacht Yard, Annapolis Landing Marina and the municipal docks.

The Blue Angels fly over Annapolis during Commissioning Week, aka the U.S. Naval Academy’s graduation ceremonies. © Photo courtesy of Jay Fleming

Solomons Island

An ideal jumping-off point for cruising the Patuxent River, Solomons Island is a popular stop along the Bay since it has great dining, plenty of attractions ashore, well-equipped marinas and friendly townspeople. This easily walkable destination caters beautifully to its waves of cruising visitors who are looking for a slower pace and gentler sense of calm in today’s world. Be sure to visit the Calvert Marine Museum, an absolute jewel that will keep kids — and kids at heart — happy for the better part of a day.

EATING: For high-quality food in a scenic setting, go to La Vela Italian at Safe Harbor Zahnisers. Hidden Harbour at Calvert Marina is a casual alternative in season. At Harbor Island Marina, Charles Street Brasserie has a novel menu and atmosphere. Dock-and-dines include Island Hideaway and The Pier.

DOCKING: Safe Harbor Zahnisers, Spring Cove Marina, Harbor Island Marina, Calvert Marina and Solomons Yachting Center.

From one generation to the next, watermen and women have been pulling crab pots from these waters for centuries. © istock.com / Mark Coulbourne Photography

Washington, D.C. and the Potomac River

Flowing for 400 miles from West Virginia’s Allegheny Mountains into Chesapeake Bay, the Potomac River forms the boundary between Maryland and Virginia. These scenic waters offer the only route to the nation’s capital by boat. Along the way upriver you’ll be able to catch sight of George Washington’s Mount Vernon plantation. You can also visit Maryland’s original capital, St. Mary’s City, where two ships landed in 1634 and established the British colony of Maryland in North America.

Washington, D.C., of course, is the Potomac River’s big draw, famous for historic sites and monuments, most of which are free to visit. Walk the National Mall and its surroundings to see the Lincoln Memorial, Washington Monument, the Vietnam Veterans Memorial and the U.S. Capitol. The White House is also within walking distance of the Mall as are many of the national museums, galleries and zoo of the Smithsonian Institution.

EATING: As a microcosm of the nation it represents, the District of Columbia is a diverse haven for all tastes and budgets. You’ll find every variety of ethnic food that you can imagine. Our editors like Rasa for fast-casual Indian, Angora for Mediterranean, Mari Vanna for East European specialties, Mandu for Korean and Alta Strada for Italian.

Few places on Earth can match the remarkable number of landmarks and museums in the nation’s capital.

There are some 30 restaurants, including an open-air fish market, alongside The Wharf, the revitalized Southwest waterfront near the Capital Yacht Club, Washington Marina and the namesake Wharf Marina. Downriver at National Harbor, more than 40 restaurants await. Ask the dockmasters and deckhands at your marina for advice and tips on where they like to go.

DOCKING: The aforementioned Wharf Marina, Capital Yacht Club and Washington Marina, plus Columbia Island Marina, which is across the river in Arlington, Virginia, right next to the Pentagon and close to Ronald Reagan Washington National Airport. The Alexandria City Marina and Washington Sailing Marina are in nearby Alexandria, where there are buses, trains and water taxis to D.C.

Stretching for a mile along the Potomac River, The Wharf has astoundingly enhanced southwest D.C.’s waterfront. © istock.com / Nature, food, landscape, travel

events

MAY DECOY AND WILDLIFE ART FESTIVAL

Have de Grace, Maryland

Chesapeake

Carvers bring their masterpieces of wooden waterfowl forms to this late spring event that benefits the Havre de Grace Decoy Museum, a Chesapeake Bay must-see.

COMMISSIONING WEEK

Annapolis, Maryland

Witness graduation at the U.S. Naval Academy with a week of activities that includes parades, dances and a performance by the Blue Angels.

JUNE ANTIQUE & CLASSIC BOAT FESTIVAL

St. Michaels, Maryland

A Father’s Day weekend extravaganza at the Chesapeake Bay Maritime Museum, an 18-acre, educational and entertaining complex. The outlaw gunners’ exhibit here amuses children of all ages.

JULY CHINCOTEAGUE PONY SWIM

Chincoteague, Virginia

On the last consecutive Wednesday and Thursday in July, wild ponies are moved from Assateague Island to Chincoteague so that the foals can be auctioned. This century-old tradition keeps the herd from growing too large and it is also a fundraiser for the volunteer fire department. The best way to view the swim is by kayak.

AUG HERITAGE REGATTA

Oxford, Maryland

A collection of wonderful, old one-design sailboats — Comets, Chesapeake 20s, Penguins and the spectacular log canoes — all Chesapeake born, put on a yesteryear spectacle at the end of August.

HOMECOMING FESTIVAL

Tangier Island, Virginia

Features local food, arts and crafts, games and helicopter tours of the island, with proceeds going to island projects. While you’re here, drop in the Tangier History Museum & Interpretive Cultural Center.

SEPT CHOPTANK HERITAGE DAYS

Cambridge, Maryland

The most surviving skipjacks (oyster-dredging sailboats) are on full display the third weekend of September with boat parades, races, a seafood festival and other events.

OCT DOWNRIGGING WEEKEND

Chestertown, Maryland

Over Halloween weekend, this Eastern Shore town honors its maritime history with a parade of historic and replica tall ships, considered America’s largest annual public sailing event. Onshore, enjoy bluegrass in the Downrigging Music Village.

NOV OYSTER FESTIVAL

Urbanna, Virginia

Expect a lot of oysters among the food, a carnival and plenty of activities for the children, wine and beer for the adults, a couple of parades and a little bit of goofiness at this annual event that is held the first consecutive Friday and Saturday of November.

JEEP FEST

Virginia Beach

The only time of the year the public is allowed to drive of the sands of Virginia Beach, this weekend event is for those who enjoy all things Jeep.

Cape Charles

Out of the mainstream and far from major cities by both land and sea, otherworldly Cape Charles is a great place to get supplies or just to rest up before or after crossing the Chesapeake. This man-made town of a thousand people boasts of two distinct and deep harbors, plus a generous white sandy beach and a walkable downtown. Its low-key presence and more-than-ample boating facilities make Cape Charles an attractive destination for anyone tired of too-busy, over-loved harbors.

EATING: For such a small town, there are many eating options. Closest to the docks are the upscale Hook @ Harvey at Cape Charles Yacht Center, The Shanty at Cape Charles Harbor and the Seafood Eatery at the Oyster Farm Marina at Kings Creek.

Sporting the look of an old-style soda fountain counter, Rayfield’s Pharmacy will make you feel as if time has stood still. It’s open for breakfast and lunch. Another looker is the Cape Charles Coffee House, which is located in a nicely decorated old bank.

DOCKING: Transient slips may be acquired at Cape Charles Yacht Center and Cape Charles Harbor.

Splashy sunsets — and sunrises — are ubiquitous in Cape Charles at the southern end of the Delmarva peninsula.
© istock.com / Jimmy Olivero

Hampton Roads

Encompassing the Elizabeth, Nansemond, James and York rivers, the Hampton Roads region is home to nearly two million residents across 15 distinct localities. Ships from the other side of the world began arriving at the sheltered harbors, or roadsteads, here more than 400 years ago, naming the place after the Earl of Hampton, an English financier who was part of the colonization of Virginia.

Historically significant Yorktown is where George Washington’s army defeated the British in 1781, effectively ending the American Revolution. Nearby Jamestown is where Captain John Smith came ashore in 1607 to establish the first English-speaking colony in the New World. Along with Williamsburg, they are part of the “Heritage Triangle,” a wideranging living museum that makes learning about the country’s history a captivating experience.

The entrance to the Elizabeth River is in the thick of commercial shipping activity at the Chesapeake Bay’s entrance. The river marks the

northern end of the Intracoastal Waterway (ICW) and the amount (and size) of traffic here can be intimidating. Norfolk and Portsmouth are the focus of row on row of barges, naval vessels, ferries, tugs and freighters. You name it — it’s here. Fortunately, pleasure craft are also welcomed, with plenty of marine facilities, services, provisions and entertainment.

Strategically located as the gatekeeper to the vast Hampton Roads ship anchorage and its larger cities, Hampton takes advantage of its smaller size and offers a number of attractions and services for the visiting mariner. To the east, outside the waters of Hampton Roads but still mostly accessible via Rudee Inlet on the Atlantic Ocean, Virginia Beach is the state’s most-populous city with nearly a half-million residents. Its 35 miles of sandy shore is accessible from the ports to the west via the affordable Hampton Roads Transit buses.

EATING: Norfolk’s Waterside District is home to a dozen or more restaurants within easy walking distance of downtown’s attractions. A couple of blocks inland, Grace O’Malley’s has

an authentic Irish pub atmosphere while the Monastery serves up Hungarian, Polish, German and Czech dishes. Also heavenly is the nearby Freemason Abbey, which is located in an old church.

Across the Elizabeth River in Portsmouth, Tidewater Yacht Marina’s Fish & Slips Raw Bar & Grille puts some new spins on casual comfort foods. (The ICW begins just off the docks here.) Joints to try nearby are Still, the Olde Towne Public House, Baron’s Pub and The Bier Garden. For breakfast, it’s Yoolk’s On Us.

Ocean views on Virginia Beach are seen at the Watermen’s Surfside Grille, Catch 31 and Mahi’s. Rudee’s and Rockafeller’s are dockside options within Rudee Inlet. In Yorktown, you’ll be just a short stroll to a legion of restaurants with a slip at Riverwalk Landing Piers.

DOCKING: Tidewater Yacht Marina and Ocean Yacht Marina alongside the ICW in Portsmouth, the Waterside Marina across the river in Norfolk, Kingsmill Resort in Jamestown, and York River Yacht Haven and Riverwalk Landing Piers in Yorktown.

A Hampton Yacht Club instructor keeps an eye on the junior sailors learning the ropes within the city’s waters. © Photo courtesy of visithampton.com

These varied environs hold eerie swamps, stirring saltmarshes, wide sounds and long barrier beaches.

Southeast

North Carolina, South Carolina and Georgia

Picking and choosing amid the possibilities in North Carolina, South Carolina and Georgia is a full-time occupation, ranging from a wide variety of cruising styles to considering numerous temptations to stray off the beaten path. Of course, you could make a bee line past these states, but that 400-plus-mile run is arduous, to say the least.

Should you go offshore, you’ll have few options should the weather turn nasty. Very few inlets offer easy passage, even during daylight conditions and with detailed local knowledge. If you choose the inland route, or Intracoastal Waterway, the slow evolution from northern vegetation and critters to a distinctly more southern look will more than make up for extra time spent.

For those wanting off the beaten ICW path, consider the Great Dismal Swamp, a wild and untamed, soggy depression in southern Virginia and northern North Carolina. Another

alternative route passes through North Carolina’s wide-ranging interior sounds, just behind the much-loved Outer Banks’ barrier islands. Fast power boats can cover about 140 statute miles in a summer’s day here.

The inland ICW passage through South Carolina starts with serene canals that feel completely removed from any saltwater environment. They’re followed by narrow rivers that transition into sprawling estuaries, followed by broad bays, punctuated with vast salt marshes and low islands that barely rise more than a few feet above sea level.

In Georgia, the twists and turns of navigating up and down tide-scoured estuarial rivers, across sometimessurly sounds and along brief canals will keep you alert. It is mostly backcountry, slow-lane cruising where Mother Nature shines and mosquitoes fly amid quiet anchorages too plentiful to count. It’s a hard-core cruiser’s dream come true.

ABOVE: Charleston’s waterfront Pineapple Fountain symbolizes the city’s hospitality. © istock.com / Sean Pavone LEFT: Piers jutting out through salt marshes are standard in this region. © istock.com / makasana

Oriental

Framed by the rivers and streams of the lower Pamlico Sound, Oriental has a soul linked to the traditions of coastal exploration. Most locals like to claim that laidback Oriental is where the boating season never ends. Whether under sail, cranking RPMs or just paddling along, permanent residents (around 1,000) and visitors alike come here for the extensive, protected Inner Banks waters that offer all sorts of possibilities, from regattas and gunkholing to reveling in festivals. Of course, Oriental’s proximity to the Intracoastal Waterway makes it an eminently logical stop for cruisers.

EATING: Overlooking the harbor and hard to miss, The Toucan Grill & Fresh Bar at Oriental Marina serves as a social center at the town docks. You’ll also find some very friendly folks at The Silos. Yawl’s Café at the River Dunes Harbor Club and M&M’s Café, a block inland of the town docks, are a couple of other options.

Try the mocha shake at The Bean, a beacon for those craving caffeine and a pastry. Inland Waterway Provision Company, a block from the Oriental Dinghy Dock, is the go-to for making something yourself.

DOCKING: River Dunes Harbor Club, Zimmerman Marine and Oriental Marina & Inn.

Kayaking on the Neuse River and its tributaries is among the group activities to enjoy at River Dunes in Oriental.
© Photo courtesy of River Dunes Development

Beaufort and Morehead City

Positioned inside one of the best inlets on the North Carolina coast, Beaufort and Moorhead City share a deep and protected harbor. These once-gritty fishing ports separated by the Newport River and just off the ICW are now popular, accommodating destinations for cruising boats. Both are small, walkable towns that are relaxed ashore, where one could spend the day casually shopping, watching the daily catch arrive at the docks while having lunch, and delighting in nature on the harbor’s islands. The Rachel Carson Reserve is on the Atlantic Migratory Flyway and more than 200 bird species have been spotted here. River otter, raccoon, marsh rabbit and feral horses are among the mammals — and bottlenose dolphins, of course.

EATING: Most convenient to the waterfront is the Dock House Restaurant at Beaufort Docks. Nearby standouts are Clawson’s 1905 Restaurant & Pub, Ribeyes Steakhouse and the Black Sheep. At the Royal James Café, the fare is mostly pub grub, the drinks are cold, and you can play billiards late into the night.

In Morehead City, a longstanding fixture is the Sanitary Fish Market & Restaurant. Also try Southern Salt Seafood Company & Waterfront Restaurant, Floyd’s 1921 Restaurant & Bar and the Red Fish Grill. Ioanni’s Grill & Bar is a good, local watering hole.

DOCKING: Beaufort Docks, Town Creek Marina and Morehead City Yacht Basin. On the ICW to the north, try Bock Marine.

Situated on the national seashore barrier island, Cape Lookout Light is a welcome beacon on the approach to Beaufort Inlet. © istock.com / Eifel Kreutz

Charleston

With protected inland waterways connected by a wide, deep natural inlet to the ocean, Charleston has always been a thriving port. It’s the physical and psychological center of the South Carolina coast, with a sprawling historic district, numerous parks, diverse neighborhoods and many major attractions. Step ashore and you’ll quickly understand why Charleston keeps popping up on various “best of” lists. All the superlatives you’ve heard about the place are true.

Comfortable shoes will stand you in good stead because Charleston is a great walking town. Its streets — some of which are cobblestone — feature picturesque churches, open-air markets, classic homes of grand design and lovely gardens. A trolley, bus or pedicab tour will help you get your bearings, and there are many. The water taxi is another option.

Perhaps the most popular locale for visitors is the Fort Sumter National Monument, the most prominent Civil War site in Charleston, on Sullivan’s Island. For a major-league military history experience, get over to Patriots Point Naval & Maritime Museum in Mount Pleasant.

EATING: The downtown district and the diverse neighborhoods offer hungry travelers nearly as many

The crown jewel of South Carolina’s coast, Charleston is a vibrant city with superb boating facilities.

ethnic cuisines as there are ethnic cultures in Charleston. You will find restaurants and cafés to suit any taste, and they range from on-the-go-casual to buttoned-up formal, inexpensive to exorbitant, historic to brand-new, and everything in between. Some have celebrity chefs; others, hash slingers — but you should never have to go underfed. Foodies have long since marked Charleston as a topdrawer, go-to destination amid major Southern cities, and deservedly so. Ask your dockmaster for their best restaurant recommendations.

DOCKING: Just off the ICW in town are the Charleston City Marina and The Harborage at Ashley Marina. At Patriots Point across the Cooper River from downtown, the Charleston Harbor Resort & Marina.

A tale about Charleston’s Rainbow Row houses is that their bright hues made it easy for drunk sailors to find their way home. © istock.com / Mak Studio

Beaufort

Styling itself as the “Queen of the Carolina Sea Islands,” Beaufort presents the ideal town setting, a picturesque entity where heritage envelops you like all of the Spanish moss clinging to the huge oak trees. When you first come ashore, handsome architecture is the most striking feature of this city of 14,000 people.

More than 300 acres of downtown are on the National Historic Landmarks registry. The high ceiling homes, with their spacious porches, lavish columns supporting endless balconies, and lush gardens with overgrowing trees, are a local signature all over downtown. The entire city is especially attractive in the springtime, when floral displays of every description abound and astound.

Celebrations pop up in Beaufort throughout the year, and perhaps the biggest shindig is Beaufort Water Festival, a week-long affair in mid-July. Likewise, a huge two-week feast is the Beaufort Shrimp Festival, held the last week in September and first week in October.

EATING: Breakwater Restaurant is a half-mile from the downtown Safe Harbor marina, while Saltus River Grille

Beaufort presents the ideal southern town setting, entirely picturesque, and that’s why so many movies have been filmed here.

overlooks the waterfront. Bricks on Boundary and the Wren Bistro & Bar are a little inland. For a special dessert, try the Southern Sweets Ice Cream & Sandwich Shop and watch the river traffic go by. Perk up in the morning at Common Ground Coffee House and take the pooch with you to dog-friendly Blackstone’s Café.

DOCKING: Safe Harbor has three facilities here and Lady’s Island Marina is across the Intracoastal Waterway in Factory Creek. Six miles east of town, Dataw Island Marina is upscale casual.

Fireworks, a fleet blessing and a boat parade are highlights of the 10-day Beaufort Water Festival, which turns 70 in July.
© Photo courtesty of Visit Beaufort, Port Royal & the Sea Islands

Attractions Southeast

NATIONAL FISH HATCHERY

Edenton, North Carolina

NORTH CAROLINA ESTUARIUM

Washington, North Carolina

THE PEPSI STORE

New Bern, North Carolina

ROANOKE ISLAND FESTIVAL PARK

Manteo, North Carolina

ALLIGATOR ADVENTURE

North Myrtle Beach, South Carolina

RICE MUSEUM

Georgetown, South Carolina

KAZOO MUSEUM

Beaufort, South Carolina

SANDBOX

CHILDREN’S MUSEUM

Hilton Head, South Carolina

BANANAS BASEBALL

Savannah, Georgia

INSTITUTE OF OCEANOGRAPHY

Skidaway Island, Georgia

Yorktown Battlefield © Roxanne Castaldy

events Southeast

MAR CHARLESTON FESTIVAL

Charleston, South Carolina

This month-long happening includes tours of more than 80 grand estates and coffee table book-quality gardens. Musical events draw inspiration from the culture and history of the Lowcountry.

ST. PATRICK’S DAY PARADE

Savannah, Georgia

One of America’s largest Irish celebrations that began in 1824, Savannah’s biggest annual event involves about 6,000 participants, 300 units and 50 floats.

APR AZALEA FESTIVAL

Wilmington, North Carolina

This beauty of the season coincides with ICW cruisers heading north in the spring. Held annually since 1948, this early April affair features concerts, a parade, a street fair, fireworks, and home and garden tours.

MAY POTATO FESTIVAL

Elizabeth City, North Carolina

A potato peeling contest, lumberjack show and free french fries — until they’re gone — are among the happenings at this weekend-long spectacle in May at Mariners’ Wharf Park.

JUNE

CORVETTES AT THE BEACH

Myrtle Beach, South Carolina

A fundraiser for local charities, the action takes place at Broadway at the Beach, where hundreds of classic and contemporary Corvettes will be on display.

JULY CROAKER FESTIVAL

Oriental, North Carolina

Named after the ray-finned fish related to the black drum, silver perch and spotted sea trout, this is two days of family fun, community spirit and patriotic celebration around the 4th of July.

AUG JUMOKE’S WATERMELON PARTY

St. Helena Island, South Carolina

Hosted by the Penn Center, an institution that safeguards the traditions of the Gullah Geechee community, descendants of West and Central Africans enslaved on the Southeast’s coastal plantations.

OCT SMOKE ON THE WATER

Washington, North Carolina

This increasingly popular barbecue cook-off has been drawing sizable crowds with the smell of sizzling meats filling the waterfront air. Includes a car show, kids’ amusements and more.

BLACKBEARD’S PIRATE JAMBOREE

Ocracoke, North Carolina

The island’s Colonial past comes alive each autumn with a historically accurate pirate encampment, a reenactment of Blackbeard’s final battle, a pirate parade, sea shanties and a lot of swashbuckling fun.

SHRIMP & GRITS FESTIVAL

Jekyll Island, Georgia

Restaurant chefs put their own unique spins on the Coastal South’s signature dish for attendees to sample. This free, family-friendly extravaganza in late October also includes a mix of bands and artisans.

Savannah

With one of the largest historic districts in the United States, along with 22 park-like squares near the waterfront, Savannah is primed for lingering. As might be expected, there are plenty of diversions and palate-tempting establishments all over the downtown. Moreover, there are many transient-welcoming marinas within the greater Savannah metropolitan area that make it easy to reach downtown from outside the city.

Savannah has scores of attractions, but before you head to a museum or a restored home, walk the city streets and soak up the atmosphere. River Street is paved with centuries-old cobblestones once used as ballast in the ships that sailed here. Go two blocks inland to Savannah City Market, a pedestrian promenade alongside 19th-century buildings, sidewalk merchants, boutiques, galleries, restaurants and clubs, making it one of the city’s trendier places.

More than a dozen tour companies vie for your attention in Savannah, offering everything from bus and trolley excursions to riverboat rides, horse-drawn carriage trips and specialized walking tours to graveyards, ghost haunts

and Civil War sites. Because there is so much to see and do here, you may want to narrow your options by checking out the Savannah Visitors Center, which is a short walk from the waterfront.

EATING: The city is well-known for its indigenous seafood, regional soul food, Lowcountry classics and highbrow fine-dining. The Pirates’ House, Huey’s Southern Café and B. Matthew’s Eatery are near the waterfront. Go a little bit inland for the bites at Alligator Soul and Mrs. Wilkes Dining Room. The City Market area has Garibaldi Café for Italian and Belford’s for seafood and steak. For pure elegance, go farther afield to Elizabeth on 37th.

American football fans gather at the Savannah Taphouse, where there are about 40 beers on tap, while English football enthusiasts hit Churchill’s, a British-style pub. Beat the heat at Leopold’s Ice Cream, a Savannah institution that’s been around for more than a hundred years.

DOCKING: The brand-new IGY Savannah Harbor Marina is just across the river from downtown. Options outside the city proper but within its orbit are Isle of Hope Marina in Thunderbolt, and Landings Harbor Marina and Delegal Creek Marina on Skidaway Island.

Founded in 1733, Savannah still looks much like it did long ago. The riverfront is one of its most visited areas. © istock.com / SeanPavonePhoto
Across a square mile of Savannah’s downtown are 22 squares awash with fountains, monuments and moss-draped trees. © istock.com / SeanPavonePhoto

If there is anywhere in the world a boater should be cruising it’s in Florida. Few places offer so much.

Florida

Bounteous waterways await explorers

Geographical features divide Florida into naturally distinct sections. Chambers of commerce have gone a step further, identifying each of the state’s coastal areas by historic, economic and recreational significance.

The First Coast, from Fernandina Beach to St. Augustine, is where some of the first European explorers came ashore in North America. Farther south is Daytona Beach and the start of the Space Coast, so named for NASA’s presence in the Cape Canaveral area. The Treasure Coast is where you’ll start to see more traffic building from Fort Pierce to Jupiter.

The Gold Coast, the stretch from Palm Beach to Fort Lauderdale and Miami, earned its name because of its wealth. Multi-million-dollar mansions and megayachts are ubiquitous. It’s a straightforward cruise past them all, albeit the waterway is crowded and the passage is sluggish.

By the time you’ve reached the Keys, memories of the bustling highrise jungle to the north fade. The Intracoastal Waterway (ICW) here intersperses wide open sounds with narrow creeks, offering peaceful, sandy-bottom anchorages. Ashore, you

may find the destinations laid-back or full of partiers, especially in Key West.

The Southwest Coast destinations range from the Everglades, where you’ll find isolation among wildlife, to Fort Myers Beach, where the excitation is a wild life. To the north, the 150-mile, inside passage of the Gulf Coast Intracoastal Waterway begins in wide-open Pine Island Sound, past Sanibel and Captiva, before intersecting with Charlotte Harbor near Boca Grande.

Farther north, the Intracoastal Waterway continues through Lemon Bay, Venice and Sarasota Bay, eventually meeting up with Tampa Bay near St. Petersburg. The most-developed area of Florida’s west coast is from St. Pete Beach to Clearwater.

As the Intracoastal Waterway ends west of Tarpon Springs, cruisers usually skip the Big Bend’s destinations, which are more fishing havens than ports of call. At Carrabelle and Apalachicola on the state’s Panhandle, the ICW resumes in St. George Sound. The Emerald Coast gets its name from the beautiful green waters of the Gulf of Mexico. Some of America’s best beaches can be found from Panama City to Pensacola.

Year-round boating in striking seas draw many to the deservedly dubbed Sunshine State.
© Photo courtesy of Bill Klipp
Fernandina Beach’s serene streets, patchwork past and spiffy shoreline present a humble and relaxing start for boaters making a southerly sojourn into Florida.

Fernandina Beach

Initially inhabited by the Timucua tribe, the first European visitor stopped by Fernandina Beach in 1562. By the time the barren peninsula was ceded by Spain to the United States in 1821, at least eight separate flags had flown over the city, making it the most diversely disputed parcel of land in the nation.

Sitting abreast the ICW, Fernandina Beach’s historic district is a 50-block showpiece of Victorian architecture. You can step inside Florida’s oldest bar and feel the sordid seafaring past. In the early 1900s, Fernandina Beach’s docks were bustling. Modern shrimping is said to have begun here, and you’ll still see shrimp boats at the docks.

DINING: Windward Amelia Island Marina’s Kitchen 251 has a large patio where you can swap sea stories with cruising comrades. At Oasis Marinas Fernandina Harbor, Brett’s Waterway Café has views of the dozens of working fishing boats. Expect the seafood to be fresh — and tasty. The Salty Pelican Bar & Grill is a good place for sunsets. Just a few doors away is Florida’s oldest bar, The Palace Saloon, where ship captains and crew have frequented since it opened in 1903.

DOCKING: Windward Amelia Island Marina and Oasis Marinas Fernandina Harbor.

Fernandina Beach is part of Florida’s First Coast, which is where the first European explorers came ashore in North America. © istock.com / Billy McDonald

St. Augustine

Founded by Spanish conquistador Pedro Menéndez de Avilés in 1565, St. Augustine is the oldest continuously occupied European settlement in United States. It was founded just a year after Renaissance man Michelangelo died and a year before Shakespeare was born. History would have to idle more than half a century before the Pilgrims would land at Plymouth Rock. This one-of-a-kind city boasts a revitalized historic district with a wealth of Spanish colonial-era buildings and elite architecture that has been lost to history elsewhere.

DINING: The Colonial Quarter’s Taberna del Caballo brings you back to an 18th century Spanish tavern and the Bull & Crown is a British-style pub fit for anyone aboard. Cuban heritage influences The Columbia Restaurant, while vegans and vegetarians will enjoy the breakfast-and-lunch Manatee Café. The Old City House Inn and The Raintree are awardwinners, while Hurricane Patty’s is the go-to for seafood — and beer.

DOCKING: Transient slips may be found at Windward Marina Group’s Camachee Cove Yacht Harbor, opposite the inlet, and the St. Augustine Municipal Marina, which is just steps from downtown.

Standard Oil’s Henry Flagler built St. Augustine’s Hotel Ponce de Leon in 1888; now, it’s a college named after him. © istock.com / SeanPavonePhoto

New Smyrna Beach

Those in search of joy should take after the late Bob Ross, the legendary painter of PBS TV fame whose art workshop and gallery is still in New Smyrna Beach. A rich cultural texture runs through the fabric of the community amid stately trees and gardens and post-Victorian houses. Some of the best fishing and shellfish stocks you’ll find along central Florida’s coast are located in the backwaters and bays here, and there’s a laid-back surfer scene that climbs over from the dependable waves near Ponce de Leon Inlet.

DINING: For seafood, Outriggers Tiki Bar & Grille at the city marina and Off the Hook at Inlet Harbor. Yellow Dog Eats Kitchen & Bar is a small and funky town favorite, while The Grille at Riverview has free sunsets accompanying its cocktails and plates. For a home-cooked breakfast or lunch, try Ruth’s Kozy Kitchen.

DOCKING: New Smyrna Beach City Marina and Loggerhead Inlet Harbor Marina.

Its
©
In Fort Pierce, be sure to visit the SEAL Museum, a national archive that preserves the heritage of the U.S. Navy’s premier special operations force.

Fort Pierce

With an inlet that is wide and easy to navigate, Fort Pierce attracts long-term boaters as well as those who await an easy hop over to the Bahamas or continue down the ICW. Lt. Col. Benjamin Pierce, whose brother would become President Franklin Pierce, established a headquarters for the U.S. Army here during the Seminole Indian War in 1838. The city eventually incorporated in 1901.

DINING: Along the water, Crabby’s Dockside at Fort Pierce City Marina is one of the best restaurants in the area. This two-floor eatery offers up decadent views alongside a delectable dinner menu. Patrons of Safe Harbor Harbortown can enjoy live music at Skippers Cove Bar & Grill. Design your own pizza or order a flatbread at The Crafted Pie at Sailfish Brewing, which is two blocks from the city marina. The nearby Fort Steakhouse is a sophisticated establishment.

DOCKING: Fort Pierce City Marina has a series of manmade barrier islands just outside the facility that provide protection for boats and habitats for wildlife.

residents from all over, Fort Pierce is still close-knit.
Donna Caruso Bowden

Palm Beaches

Florida’s Gold Coast earned its name because of its wealth. It is only appropriate that it starts in Palm Beach, where mansions are as big as your child’s school back home and manicured landscapes make most botanicals gardens green with envy.

Yacht spotting is practically a sport in the Palm Beaches, where wealth is fully on display and you can see some of the finest personal vessels ever built. Home to legendary resorts, world class museums and opulent mansions, this is where the rich come to play and unwind. Thankfully, anyone with a boat and enough money to dock for a night or two can gain access to this amazing stretch of real estate that stretches along both sides of the Intracoastal Waterway.

On the ocean side, be sure to walk Worth Avenue, often called the “Rodeo Drive of the East Coast” for

its high-end boutiques and celebrity appeal. On the mainland, the historic heart of downtown West Palm Beach is Clematis Street, a must-see with its night-owl nightclubs, tony restaurants and trendy shops.

DINING: On the mainland, Café Chardonnay and Carmine’s La Trattoria are known for exquisite presentations and ambitious menus. Soccer and football fans like Duffy’s Sports Grill.

On the beach side alongside luxurious and sensual Worth Avenue, Bice Ristorante and Renato’s are at the top of the dining list. Rafiki Tiki Bar & Grill is a casual spot at the Riviera Beach Marina Village.

DOCKING: Riviera Beach Marina Village is opposite Lake Worth Inlet, providing easy Atlantic Ocean access. Farther south on the ICW are the Palm Beach Town Docks. Loggerhead Marina Palm Beach Gardens is an option to the north.

It’s worth every penny, bitcoin or bullion to wander Worth Avenue in Palm Beach.
istock.com
Crystal Bolin Photography

Fitness- and leisure-inclined travelers will find plenty of opportunities on or alongside legendary Fort Lauderdale Beach.

© istock.com /

Fort Lauderdale

With its 165 miles of navigable waterways and the greatest parade of boats you’ll ever see, Fort Lauderdale has rightly been dubbed the “Venice of America” and the “Yachting Capital of the World.” Famed marinas, superb service facilities, dock-anddine restaurants and jaw-dropping superyachts have long lined the canals, rivers and stretch of the ICW here. Expect sensory overload when you add the manufactured, mountainous landscape of high-risehotels, condominiums and mansions. Behind the metropolitan-jungle facade is an affording city that welcomes visiting yachtsmen as though they were long-lost relatives.

The New River leads the way into the heart of the city and Riverwalk, with the tony and eclectic stretch of Las Olas Boulevard nearby. There is something for everyone from Segway, electric bike and party bike tours, to a taco battle and jazz brunch, yearround activities at Esplanade Park,

a historical society campus and a nightlife scene that will keep you smiling ’till the wee hours.

At the shore, you will find one of the most iconic sand spits in America, with a 2-mile-long wall lining the promenade. From families to bodybuilders to retirees, everyone who loves the beach finds it to be a mecca for relaxation and people-watching.

One of the best ways to experience Fort Lauderdale is on the water taxi. It’s a great way to get around while listening to running commentary.

DINING: Longstanding and well known among the resident boating crowd is 15th Street Fisheries. Other dock-and-dine options are the Boatyard restaurant, Southport Raw Bar and Coconuts. There are a dozen distinct culinary destinations at Pier Sixty-Six, with cuisines of France, Spain, Italy, Greece and the eastern Mediterranean well represented. The signature feature — quite literally — is Pier Top, a rotating bar on the 17th floor of the legendary resort.

Not far from the northernmost Intracoastal Waterway facilities by the Sunrise Boulevard Bridge are The Capital Grille, Blue Martini and Seasons 52. All of these are upscale, destination restaurants.

Along Las Olas Boulevard, a lively, tree-lined street stretching from downtown to the beach, get some finger-lickin’ wings and sliders at B Square Burgers & Booze, awardwinning meatballs at Noodles Panini and sophisticated steak at Del Frisco’s Grille. Farther afield, you’ll need a ride for fine Italian at Casa D’Angelo and the Café Vico.

DOCKING: Pier Sixty-Six Marina is closest to the inlet, while Bahia Mar Yachting Center, Hall of Fame Marina and Las Olas Marina are alongside the world-renowned beach. In the heart of the city are Marina Bay Resort, New River Downtown Docks and Cooley’s Landing. Within Fort Lauderdale’s orbit are Seahaven Superyacht Marina and Harbour Towne Marina on the Dania Cut-off Canal and the Dania Beach Marina.

Mariakray

Miami Beach

Located on what was long ago a mangrove-tangled spit of land, Miami Beach is best known for the legendary nightlife of South Beach and the neon lights of the Art Deco District. It sports a wide swath of sandy white Atlantic coastline and is known for hosting models and celebrities. Floral and aquatic embellishments and nautical designs reminiscent of ocean liners are a central theme here. They provide a colorful backdrop for the nightlife at South Beach that has become the stuff of legend, as are the stories that get told afterward on the docks and nicely-endowed decks.

Be sure to visit the Art Deco District twice: first in the daytime and again

in the evening. Feast your eyes on retro architecture and pastel-colored buildings, flashy limousines and movie stars, sidewalk cafes and psychic parlors, Hassidic Jews and in-line skaters, rich and poor, welldressed and barely dressed — and you’ve only walked a block. For even more, beat your feet over to the Art Deco Welcome Center on Ocean Drive, the heart of Miami Beach.

Whether you’re going to swim or watch the crowds, South Beach is a must. Evenings are especially entertaining. Have a cool drink at a sidewalk café and enjoy the show. A quieter option to the north is Haulover Beach, a top tier spot to fly a kite, board one of the fishing boats or get naked, as the northern third of the beach is clothing optional.

DINING: Ice Box Café is a Miami Beach staple. It’s close to Miami Beach Marina and Sunset Harbour Yacht Club, as are Sardinia Enoteca Ristorante, an upscale Italian joint, and the casual Stiltsville Fish Bar. Miami Beach Marina itself has Monty’s Sunset, noted for its seafood, and Texas de Brazil, a steakhouse where meat is carved tableside. Joe’s Stone Crab, a Miami Beach institution for more than a hundred years, and Smith & Wollensky, are very close to the marina.

DOCKING: Miami Beach Marina has the easiest access to the Atlantic Ocean — and South Beach. Venetian Marina & Yacht Club is across the harbor in downtown Miami. Nearby, Williams Island Marina in Aventura and Turnberry Marina in Hollywood.

Miami Beach is a trendy, legendary hotspot, a destination that must be seen twice: once in the day and again at night. © istock.com / MDV Edwards

Islamorada

A village incorporating six neighboring Florida Keys, Islamorada is tucked between Everglades National Park and the Florida Strait. It’s an expansive area, relatively speaking, packed full of fun-in-the-sun possibilities in a laid-back atmosphere. It’s also the sportfishing capital of the world with an armada of charter boats and skilled guides at your service and fish that are ready and willing just moments from the dock. In between all the fishing, you’ll also find opportunities to go snorkeling, scuba diving, parasailing, eco-touring or to simply relax on the beach. As family destinations go, this is one of the best.

DINING: The favorite haunt for charter-fishing captains and crew are Lorelei Restaurant & Cabana Bar and the Green Turtle Inn. Hog Heaven Sports Bar & Grill is laid back by day and hoppin’ at night. Take your date to Meze Morada, which offers a healthy menu of eastern Mediterranean cuisine with sharable plates that local millennials always rate highly.

Start the day with breakfast at the Island Grill or Mangrove Mike’s Café, which also serves lunch. Both are popular with locals and tourists alike.

DOCKING: Plantation Yacht Harbor, situated within the city’s Founders Park, is one of the finest municipal marinas you will ever find.

Islamorada is a fishing mecca, luring politicians, pro athletes, celebrities and regular folks to its waters as if they were ants marching to a picnic.
Dawn’s early light in Islamorada, a family-friendly destination where its adventures can keep one busy all day. © istock.com / Kruck20

Key West

Rarely does a destination proudly strive to live up to a cachet as a gluttonous, gangbusting getaway. Of course, it’s this rakish reputation that has made Key West famous since it was settled by pirates in the 1820s.

Key West has always been a magnet for those who march to their own drummer. Writer Ernest Hemingway and singer Jimmy Buffett are the most notable artists who’ve heralded the island’s excessive imbibing and free-wheeled spirits. Through their far-reaching words both have heralded the island’s penchant for sensory pleasure, helping to draw even more people to this two-by-four-mile patch of fossilized coral.

It’s easy to get around on foot, bike or scooter, but you can best establish a perspective by hopping on a guided tour past the historic seaport and the

lovely homes and gardens reflecting the Bahamian, Cuban and New England influences on the island. Your first evening — or every evening — should include the ritualistic sunset celebration at Mallory Square. You’ll wish you had several sets of eyes so you can watch for that fabled green flash at the same time as getting a shot of the dock’s performers, ranging from sword swallowers and dancing dogs to unicycle acrobats and clever mimes.

DINING: From junkyard, chic fish shacks to elegant, white table cloth establishments, Key West has it all. Most of the marinas here have dockside dining so you won’t have to go far for a bite. Additionally, most outdoor and streetside venues welcome well-behaved pets to sit beside your table.

Within Key West Bight, Conch Harbor Marina has two restaurants: Dante’s, a casual yet upscale establishment, and Prime 951, a sophisticated

steakhouse. Nearby, The Boat House Bar & Grill is where many go for happy hour, Schooner Wharf Bar is where the racers hang and Half Shell Raw Bar is a relaxed joint. Other favorites of locals are Conch Republic Seafood Company, Blackfin Bistro and Sloppy Joe’s Bar, where many like to congregate after dinner.

On Stock Island, The Perry Hotel & Marina has Bad Boy Taqueria & Tequila for Mexican eats, Matt’s Stock Island Kitchen & Bar for breakfast and dinner, and the Salty Oyster Dockside Bar & Grill for happy hour. The Hogfish Bar & Grill at the Safe Harbor Marina here is noted for its freshcaught fish.

DOCKING: Along the bustling waterfront is Conch Harbor Marina. Away from the hubbub over on nearby Stock Island, The Perry Hotel & Marina and Stock Island Marina are overflowing with comforts and services for boaters.

A place of special character — and characters — Key West is heaven for freewheeling musicians and skillful freethinkers.
© Photo courtesy of Bill Klipp

Sanibel and Captiva

The miles of pristine, white, sandy beaches on Sanibel and Captiva islands contribute to a general air of rest and relaxation. With gentle Gulf waves lapping the shores on most days, a general drift toward tranquility seems unavoidable. Flip-flops define the attitude and atmosphere of these two islands.

Both islands are accessible by car from the mainland and officials make no bones about attracting as many visitors as possible every year. Nevertheless, the nearly 7,000 yearround islanders have done a stellar job of balancing a compelling desire for tourism while maintaining some of their small-town charms. The area is full of beaches, nature preserves, bike trails and waterside activities.

DINING: Old Captiva House combines the classics with the contemporary in an old school building from the early 1900s. ’Tween Waters Inn’s restaurants, The Shipyard and The Crow’s Nest, honor Florida’s rich fishing and boating legacy. Farther up island at the blossoming, luxurious South Seas Resort, the Harborside is a steak- and seafood-lover’s paradise. Other island hotspots include The Green Flash Waterfront Restaurant and the Mucky Duck.

On Sanibel, your pooch is welcome at Gramma Dot’s Seaside Saloon, a dockside restaurant at Sanibel Marina. The Lazy Flamingo and Doc Ford’s Rum Bar & Grille are magnets for many. Early risers and those wanting a lunch bite have the Lighthouse Café and the Sanibel Bean.

DOCKING: Both South Seas Island Resort and ’Tween Waters Inn Island Resort & Spa are amenity-laden.

With all the natural wonders and entertainment options, there is no way to enjoy all that these islands have to offer in the span of a short stay, which is just one of the reasons to return time and again.
Sandy shores and shell seekers go hand-in-hand on the enclaves of Sanibel and Captiva, two islands that seem a world away.
© Matt / Adobe Stock

Fort Myers Beach

As the southernmost Gulf of Mexico destination for spring break activities, Fort Myers Beach is indeed a warm, sandy nirvana. Perched atop the barrier island of Estero, its northern tip is where most of the hubbub takes place. FMB, as the locals say, decided long ago to diversify a bit with festivals, waterway tours and backcountry navigation opportunities too. Now it attracts droves of additional visitors and water enthusiasts every year, year ‘round.

DINING: Fresh Catch Bistro and Pinchers Crab Shack are seafoodcentric spots, while the casual Nervous Nellie’s features a rockin’ bar and the occasional band. For some island cuisine and vibes, swing over to Parrot Key Caribbean Grill. Pink Shell Beach Resort & Marina has four restaurants covering all of the food groups and meal times.

DOCKING: The first facility coming in from the Gulf of Mexico is Pink Shell Beach Resort & Marina.

Boca Grande

The breathtaking village of Boca Grande is a must for every cruiser’s

itinerary. Sugar-sand beaches, topnotch fishing and a tranquil pace dominate the atmosphere here. Its pink and turquoise houses — there are no high-rise condos — resemble a box of pastel-colored, after-dinner mints. You can see most of the residences when riding a golf cart, the preferred transportation for getting around the cay, which is officially known as Gasparilla Island. It’s part of the self-sufficient spirit one finds in such detached places.

DINING: The exquisite Eagle Grille and laid-back Miller’s Dockside are both located at the Boca Grande Marina. Many are lured into the Temptation Restaurant & Bar, which offers gluten-free options among its seafood-oriented menu, and The Pink Elephant, an island fixture for more than 60 years. Breakfast and lunch favorites are The Loose Caboose and the Outlet Restaurant at The Innlet.

DOCKING: Boca Grande Marina takes vessels up to 130 feet LOA.

Fort Myers Beach is a playground for children of all ages. © istock.com / SerrNovik
Boca Grande’s Gasparilla Inn & Club has been around for more than 100 years.
istock.com / csfotoimages

events Florida

MAR ORCHIDS IN BLOOM

Coral Gables

An American Orchid Society-juried show with more than 10,000 orchid plants, garden workshops and walking tours at Fairchild Tropical Botanic Garden the second weekend in March.

APR HIGHLAND GAMES

Dunedin

A weeklong tribute to Dunedin’s ties to Scotland with tens of thousands of kilt-wearing folks from around the world dancing, drinking and playing traditional games.

LAS OLAS WINE & FOOD FESTIVAL

Fort Lauderdale

The 30th annual jubilee takes over four blocks of Las Olas Boulevard with dozens of restaurants and wineries highlighting the best of the region.

ISLE OF EIGHT FLAGS SHRIMP FESTIVAL

MAY

JUNE

Fernandina Beach

Decorated shrimp boats, a shrimp queen pageant, shrimp feasts, shrimp parade and lots of entertainment the first weekend of May.

HISTORY FESTIVAL

St. Augustine

The five-day jubilee in early May lauds the city’s history — the historical, the notable and the unimaginable — from its founding in 1565 until today.

SUMMER FRUIT FESTIVAL

Homestead

A two-day event at the 37-acre Preston B. Bird/Mary Heinlein Fruit & Spice Park, a tropical botanical garden with endless varieties of mangos, bananas, guavas, lychees, bamboos and other exotic edibles.

JULY HEMINGWAY DAYS

Key West

Don’t miss the Ernest Hemingway lookalike contest, along with book signings by authors of interest, at the 45th celebration honoring the famed writer who once lived in Key West.

AUG

DANCEAFRICA MIAMI

Miami Gardens

An exceptionally high-spirited, three-day affair that bridges cultural gaps with family friendly, multi-cultural arts, including dance and music.

SEPT BULLS ON THE BEACH

Pensacola

Flora-Bama’s version of the running of the bulls has three nights of rodeos with themed nights for fans.

OCT FISHING RODEO

Destin

This month-long tournament awards more than $100,000 in prizes and gifts to thousands of anglers. Even if you don’t fish, attending the weigh ins each day is a lot of fun.

NOV RACE WORLD OFFSHORE WORLD CHAMPIONSHIP

Key West

The harbor transforms into an electrifying arena for the seasonal finale featuring the world’s best powerboat racers.

to be amazed at the

Sarasota and Longboat Key

A tourism and retiree mecca, Sarasota is an upbeat community that’s easily accessible to boaters. The core population of 55,000 grows significantly during the winter months, but it’s no circus, even though it was the winter home of John Ringling, one of the five brothers who gave the world the legendary Ringling Brothers and Barnum & Bailey Circus. His 66-acre, bayfront estate, which he donated to the state, is now a museum.

Just outside Sarasota to north, Longboat Key captures the upscale market. Many come to the 10-milelong island for its tranquil atmosphere, quiet beaches, stunning sunsets and proximity to Sarasota’s cultural scene.

Sample its luxuriousness from the Resort at Longboat Key Club, which is situated mid-island.

With a lively night life, an upbeat arts community and a Major League Baseball spring training facility in its midst, Sarasota is a tourist and retiree playground.

DINING: With more than 800 restaurants in the region, Sarasota is a foodie’s heaven. Pull your dinghy up to the beach at O’Leary’s Tiki Bar & Grill on Bayfront Park.

Across the harbor, dock and dine at The Old Salty Dog and the New Pass Grill & Bait Shop. Not too far away is the Columbia Restaurant, a 60-year-fixture at St. Armand’s Circle, a popular shopping and dining district overflowing with opportunities. Here, there is the informal Cha Cha Coconuts and the Blue Dolphin Café. Myriad coffee houses, delis and ice cream shops are in the same vicinity. Over at Siesta Key, Ophelia’s on the Bay is a romantic’s dream.

DOCKING: Marina Jack abuts a terrific waterfront park alongside downtown and Longboat Key Club Moorings is on the aforementioned barrier island.

Prepare
late circus owner John Ringling’s home, a Venetian-like palace that is a must-see in Sarasota. © istock.com / Marje

Attractions Florida

RIGHT WHALE FESTIVAL

Amelia Island

NASCAR RACING EXPERIENCE

Daytona

KENNEDY SPACE CENTER

Merritt Island

LOGGERHEAD MARINELIFE CENTER

Juno Beach

MUSEUM OF DISCOVERY & SCIENCE

Fort Lauderdale

WILD BIRD

REHABILITATION CENTER

Islamorada

BAILEY-MATTHEWS

NATIONAL SHELL MUSEUM

Sanibel

BROHARD PAW PARK & BEACH

Venice

WORLD’S SMALLEST POLICE STATION

Carrabelle

NATIONAL NAVAL AVIATION MUSEUM

Pensacola

St. Petersburg

Fish gotta swim, birds gotta fly and cruisers gotta make a stop at St. Petersburg. With an entire urban waterfront essentially dedicated to pleasure boating, plus scads of handy diversions readily accessible, it’s no wonder that everyone from the lofty superyachts to glorified dories pause here and take in this Tampa Bay boating hotspot.

With free public transit close at hand, it’s easy to become enthralled in the vibrant downtown or head all the way out to the beaches west of the city. From skyline to shoreline,

St. Petersburg and its sunny beaches have so many activities and attractions that it’s hard to keep track of them all.

One good clearinghouse for all of the possibilities is the St. Petersburg Area Chamber of Commerce, which is in a location handy to downtown’s municipal marina. Of course, the dockmaster and crew at St. Petersburg Marina are also excellent sources of local knowledge.

DINING: Hundreds of eating possibilities exist all over downtown, but perhaps the nearest and best is Fresco’s Waterfront Bistro, which is a lively eatery overlooking the marinas that serves fine food and beachy

adult beverages. The rooftop lounge Birchwood Canopy has expansive views of the St. Pete waterfront. Not too far away is BellaBrava, a casual, Italian eatery.

Near the St. Petersburg Yacht Club, Ceviche Tapas Bar features some superlative Latin American, seafood and vegan dishes. Find a lot of fresh fish and fancy drink concoctions at The Big Catch at Salt Creek.

DOCKING: Located behind a breakwater and abutting the bustling downtown and its attractions, the expansive St. Petersburg Marina is one of the best municipal facilities in Florida and, maybe, America.

St. Petersburg’s waters are a bit reserved, resembling the city’s low-key demeanor, an appealing trait to many visitors. © Photo courtesy City of St. Petersburg

Florida’s largest city marina welcomes you!

• Within footsteps of the docks are miles of downtown waterfront parks, America’s No. 1 Arts Destination with world-renowned museums, galleries and live theater, plus other downtown amenities including first-class hotels, restaurants, shopping, Major League Baseball with the Tampa Rays, and more.

• 650 Slips, accommodating vessels up to 100', 500-foot transient dock (10' depth), and 13 mooring buoys in the Vinoy North Basin.

• Electric, water, phone, cable TV hook-ups, laundry, showers, 24-hour security, charters, Sailing Center, boat ramps.

• Picnic shelters and playground.

• Ship’s Store with commodities, gas, repairs, tackle, live and frozen bait.

• Courtesy docks for short-term docking downtown.

Bahamas

An easy getaway from the U.S.

Everyone needs a place to play. Children have sandboxes and explorers have the Bahamas. Whether it’s solitude and relaxation you crave or partying it up in port with a group, you can have the best of both on one of its 700 islands

The skies are as clear as the water, the seemingly never-ending, soft sandy beaches are as inviting as the people, and paradise is only a day sail from Florida’s east coast. No wonder the Bahamas are a premier destination.

Take your place at the tiller with history’s captains, rounding islands not knowing what you’ll find on the other side. Across nearly 100,000 square miles of ocean, only a few dozen islands in the Bahamas are actually inhabited. And each new destination is just a few hours’ sail

to the next so you can revel in an authentic Bahamian village, cast a line in a fishing outpost, spoil yourself in a tony resort or enjoy what feels like your own picture-perfect cove.

Cruising the Bahamas is much more than just a visit to a watery Eden. Serendipity rules as you let yourself imagine that you just might be the first person to drop anchor in a perfect cove. You’ll discover new adventures with each island.

Did you know that a miscalculation on Christopher Columbus’ route west landed him in the Bahamas in 1492? He found the Lucayans, as Columbus came to know them, to be intelligent and kind, a description shared by many adventurers. Sometimes, you just have to get lost to discover something great. That’s the attitude to have here.

Harbour Island’s waters are the epitome of Bahamas cruising.
© Photo courtesy of Valentines Resort & Marina

Bimini

The gateway to the Bahamas, the Bimini Islands are so close — just 43 nautical miles from Miami — that you can get there in a few hours in a fast boat. Even a cruising sailboat can easily make it overnight in typical conditions. The region made famous by Hemingway’s Islands in the Stream includes the twin islands of North and South Bimini as well as a string of islets trickling southward to South Cat Cay, South Riding Rock, and a few small rocks beyond.

One of the most-visited of all of the Bahamas islands, Bimini is a hangout

for sportfishermen who participate in its numerous tournaments held around its waters, and one can expect the harbors to be crowded during those times. Sportsmen and their families will find excellent service and hospitality at Bimini Big Game Club, which has been at its current location since 1954, although the club originally started in 1936.

Grand Bahama

The third largest island of the Bahamas is rarely called by its name: It’s usually West End, Freeport or Lucaya, the major destinations. West End is about 67 miles from both

Florida’s St. Lucie Inlet and Fort Lauderdale/Port Everglades, and it’s approximately 54 miles to the Palm Beaches. A welcome respite after crossing the Gulf Stream, West End is a convenient place to clear customs and spend the night before heading to other islands.

On the island’s south side, Freeport is the second most populous city in the Bahamas. It consists of five harbors, the busiest is the westernmost, where cruise-ship passengers disembark. Recreational boaters head east to Lucaya, which bustles with fishermen and land-based tourists who patronize the casinos and laze away on the beaches and in the bars.

A hammock awaits you, your cocktail and your selfies at Bluff House Beach Resort on Green Turtle Cay.
©Photo courtesy of Bluff House Beach Resort and Marina

Abaco

Only 180 miles from West Palm Beach, Abaco consists of more than 100 cays with friendly residents welcoming you to their communities. The “mainland” is the long and narrow Great Abaco Island, which stretches for more than 100 miles from northwest to southeast. Its hub is Marsh Harbour, where more than half of the 11,000 Abaconians live and a top pick of cruisers who wish to spend an entire winter in the Bahamas.

Some of the islands most visited by boaters are Green Turtle Cay, Man-O-War Cay and Elbow Cay, which is better known as Hope Town. The latter is easily identified by its 120-foot-high, Elbow Reef Lightstation, perhaps the Bahamas’ most recognizable landmark. It is the only remaining lighthouse in the world to be hand-cranked and kerosene-burning.

Founded in 1786 by British loyalists who were fleeing post-Revolutionary War America, Green Turtle Cay is located three miles east of Great Abaco. Its main settlement is New Plymouth, which some people compare to a New England fishing village. Many travelers sojourn to the Bluff House, a 12-acre haven on the highest point of Green Turtle Cay. It is steeped in history, the first and oldest resort in what are known as the Bahamas’ “Out Islands.” One of several full-service resorts with marinas on Green Turtle Cay, the Bluff House’s list of amenities include two restaurants, two bars, a tennis court and swimming pool.

Nassau

Located on New Providence Island, where two-thirds of the country’s citizens live, Nassau is a world apart from the rest of the Bahamas. It is a metropolis, complete with all the spice a city in the states can dish up. Topnotch amenities are but a stroll from the waterfront.

You can anchor right in the harbor, but many boaters find Nassau a great place to take a slip in a marina. The ritzy Atlantis on Paradise Island on the north side of the port is a top pick, especially for very large yachts.

Nassau is hands-down the best place in the Bahamas for provisioning, and it is where boaters see the cheapest fuel. Visitors find most of the same foods as in Florida, along with the islands’ best inventory of marine parts. Prices vary from 20 percent to 100 percent higher than the states.

Exumas

Beginning with an easy daysail from Nassau, the Exuma Cays offer almost 100 nautical miles of some of the Bahamas’ most spectacular scenery. The possibilities for gunkholing through here are nearly endless.

All along the Exumas chain, breathtaking underwater paradises will captivate the casual snorkeler, adventurous scuba diver and intrepid spear fishermen alike. In 1959, the world’s first land and marine national park was established here to protect these national treasures.

Along one’s passage, cruisers will find small settlements of friendly Bahamians who go out of their way to make everyone feel welcome. Provisions, fuel and good anchorages

are all available, but shoreside facilities are often limited. At the tail end of the Exuma chain, George Town in Elizabeth Harbour on Great Exuma is the southern terminus for many cruisers, who always find a party happening here.

Eleuthera

If you’re heading north from the Exumas, Eleuthera and its nearby neighbors, Spanish Wells and Harbour Island, are right smack in your path. A hundred miles long, the island of Eleuthera is not one of the most popular cruising destinations because its geography offers challenges that don’t interest most yachtsmen: shallow waters on the inside and treacherous reefs on the outside, few hospitable harbors, and what cruisers call “fierce tides.”

Even so, the few people who visit Eleuthera, Spanish Wells and Harbour Island often go back many times because the people are so friendly and the scenery so unusual.

Dunmore Town is the official name of the settlement on Harbour Island, but Eleutherans love the place they simply call “Briland,” a slurred contraction for Harbour Island. This outpost is not easily reached by tourists, which makes it an especially attractive destination for the famous and the rich — some refer to it as the “Caribbean Nantucket.”

On Harbour Island, Valentines Resort and Marina has transient slips with berths for large yachts, plus diesel fuel and reverse-osmosis water. Valentine’s also has two on-site restaurants, a pool and hotel accommodations just in case the crew needs a night ashore.

The “pig deal” at Big Majors Cay is that the resident colony of feral swine swim out to people and boats in search of treats. © istock.com / Grant Ancevic

Virgin Islands & Puerto Rico

Serene cruising and considerable charm

Stretching nearly 200 miles along latitude 18 degrees north where the Caribbean Sea meets the Atlantic Ocean is an island-studded paradise divided politically into American and British territories. With hundreds of anchorages only a few miles apart from one another, many consider the Virgin Islands and Puerto Rico the best boating grounds on the planet. Sailors delight in the combination of spectacular cruising with a huge choice of protected anchorages—lively or deserted.

The topside landscape is ecologically varied from steep green hillsides to white sand beaches, from cactusencrusted rock formations to quiet mangrove lagoons. Man added the sugar mills, great houses, historic forts, beachfront bars and duty-free shopping. Bright azure water, few currents, and a wide variety of marine

life on rock and coral reefs complete this paradise with comfortable and rewarding fishing, snorkeling, diving and shoreline kayaking.

The hub of cruising here is Tortola, the bareboat capital of the Caribbean, if not the world. It is about equidistance between St. Thomas in the U.S. Virgin Islands and Virgin Gorda, the traditional, easternmost destination in the British Virgin Islands. You could sail a passage between the two in a day, but there are too many ports of call in between.

The islands were named “Saint Ursula and the 11,000 virgins” by Christopher Columbus on his second voyager to the New World in 1493. The discoverer was honoring a mythical group of martyrs, but he might as well been referring to all the ports, gunkholes and cays.

There’s a seat waiting for you at the Bitter End, a true island getaway.
© Photo courtesy of Bitter End Yacht Club

There’s an endless array of snorkeling opportunities within the accessible, shallow bays and reefs. © istock.com / cdwheatley

U.S. Virgin Islands

Purchased from Denmark in 1917 by the United States for $25 million, the U.S. Virgin Islands consist of the three main islands, St. Thomas, St. John and St. Croix, and 50 or so surrounding minor islands and cays. Culturally, it’s only American in government and nothing close to anywhere on the mainland. Its natural beauty, seemingly endless sunshine and relative moderate temperatures are why so many people travel here.

The most-developed of the U.S. Virgin Islands, St. Thomas has always been a popular tourist destination. Nearly two million visitors arrive here annually on cruise ships and another million by aircraft. The old Danish waterfront in Charlotte Amalie (town, as it is known) is a duty-free shopping mecca on St. Thomas, where half of the territory’s 90,000 people live.

Yacht Haven, just east of town, and Crown Bay, on the western fringe of town, are the places most boaters head when coming into Charlotte Amalie. Yacht Haven Grande Marina, Crown Bay Marina and Frenchtown Harbor Marina have dockage for visiting mariners. Provisions, supplies and repairs are nearby.

The East End offers quick access to St. John and the British Virgin Islands and is where most liveaboards reside. Provisions are easy to locate in Red Hook, and repairs are generally made in Benner Bay, which is where many residents move their boats when hurricanes approach. Sapphire Beach Marina, Compass Point Marina and American Yacht Harbor have transient slips on the East End.

On St. John, two-thirds of the island is national park, offering tranquility and scenery for all visitors. Nature trails, historic remains of sugar plantations and flora and fauna abound. Town is Cruz Bay, where

you’ll find fine restaurants, a ferry dock and the customs office. Coral Bay is home to many liveaboards and the appropriately named Hurricane Hole.

The favorite destinations for boaters are located on the north shore of St. John. Caneel, Hawksnest, Trunk and Cinnamon bays are very popular for their picture-perfect beaches; Francis Bay is a noted anchorage; and Leinster Bay is just a short hike to the Annaberg historic plantation site. The anchorages and moorings in most of St. John’s bays are managed by the national park.

St. Croix is the largest in area of the U.S. Virgin Islands, and is situated 35 miles south of St. Thomas and St. John. It is home to two towns, Christiansted and Frederiksted, where you’ll discover that fine restaurants, provisions and supplies are easily accessible. Sugar mills, greathouses, historic forts, beautiful beaches, and great snorkeling and diving make it a worthy adventure.

British Virgin Islands

A British Overseas Territory, the British Virgin Islands (or simply, the BVI) consist of Tortola, Virgin Gorda, Anegada and Jost Van Dyke along with more than 50 smaller islands and cays. Its population, British citizens, is around 35,000 people, and its economy relies heavily on tourism, especially boaters, as it is considered the bareboat capital of the Caribbean, if not the world.

Nearly three-quarters of the BVI population lives on Tortola, the hub of the territory. Cruise ships call here, as do many small airlines on Beef Island that travel to and from Puerto Rico, the USVI and downisland. Both West End (Soper’s Hole) and Road Town have customs offices and offer restaurants, supplies and repairs for the visiting yachtsman.

Must-visits include neighboring Salt, Peter, Cooper and Norman islands, where you can enjoy deserted coves and beaches even at the height of the tourist season. Take a break from relaxation with great snorkeling and diving in the caves and on the reefs nearby, especially at Ginger Island.

A few miles east of Tortola is Virgin Gorda, aka the “Fat Virgin,” so called because the island’s landscape is one half mountainous, the other flat, making it look pregnant. The real wonder here is the Baths, a giant pile of boulders that were naturally dispersed at the southern end of the island. Wander through the shaded tidal pools, crevices, ledges and caves. A quieter attraction is Gorda Sound, where most cruisers make their last stop at the beloved Bitter End Yacht Club. This legendary and luxurious hangout is where travelers have endless opportunities to interact with the seascape while indulging in the resort’s extravagances.

Jost Van Dyke is one big happy hour that caters to the boating community, particularly the daysailing crowds from St. Thomas, St. John and Tortola. Swim ashore at White Bay to visit the Soggy Dollar Bar to figure out how it got its name. The bar, which has been around for more than 50 years, invented the world-famous, rum-based Painkiller cocktail. (It’s definitely worth trying.) Foxy’s in Great Harbour is noted for its New Year’s Eve bashes. Little Harbour is a quieter anchorage, and nearby Green Cay and Sandy Cay are worth a visit.

If you want to visit a place like no other in the Virgin Islands, Anegada is it. A flat coral and limestone island, unusual terrain for this area, it is home to Horseshoe Reef, the thirdlargest reef in the world, extending for 11 miles. Of course, it’s this reef that keeps many inexperienced captains at bay and makes Anegada a peaceful retreat for divers and anyone looking to truly get away from it all.

Jump into something new and exciting at the Bitter End Yacht Club, a family-friendly destination that seems a world away.
© Photo courtesy of Bitter End Yacht Club

Puerto Rico

An unincorporated territory of the United States under the designation of a commonwealth, Puerto Rico is home to more than three million people, most of whom live around the capital of San Juan. Taxis, buses, públicos (public cars) and rental cars make it easy to see the city and the rest of the 3,500-square-mile island. Knowing some Spanish will help you in Puerto Rico, but it is not necessary, as most everyone speaks English.

Head to Old San Juan to see its historic and cultural sites. El Morro, a massive 16th-century Spanish fortress, guards the entrance to the harbor and is just one of the unique attractions here. The neighboring communities of Santurce, Condado and Isla Verde offer nightlife, casinos and beaches.

Ponce is the major city on Puerto Rico’s south coast with a charm that

stems from a blend of neoclassic, Creole and Art Deco styles. The yacht club has an anchorage and facilities for visiting boaters. Museums, shopping, restaurants and a host of marine services are available to cruising boaters in Ponce. To the east, Salinas is where hurricane holes can be found.

Also providing protected anchorages to cruising boaters along Puerto Rico’s south coast are the numerous small mangrove cays off of La Parguera. The fishing village is known as “Phosphorescent Bay,” because of the bioluminescence phenomenon that is best seen on moonless nights. Excellent snorkeling and fishing can be found on the outlying reefs.

Puerto Rico’s east coast is home to several top-notch marinas, which are in close proximity to the Virgin Islands. Palmas del Mar is a major resort with numerous amenities for boaters. To the north is Puerto del Rey, the Caribbean’s largest marina. Grand

Caribbean Marinas has six facilities in and around the municipality of Fajardo, a popular fishing and sailing center that offers relatively easy access to the 28,000-acre Caribbean National Forest, or El Yunque, as it is commonly known. The only tropical rain forest in U.S. jurisdiction is thick with vegetation and wildlife that will delight the senses.

Just off Puerto Rico’s east coast is a collection of islands referred to as the Spanish Virgin Islands. Culebra and Vieques are commonly known, while the others, especially in the chain of La Cordillera, are popular among scuba divers and snorkelers.

Culebra features a fine, soughtafter hurricane hole in Ensenada Honda. Much of the island and the surrounding cays are protected by the U.S. Fish and Wildlife Service as a nature preserve. The island’s town is Dewey, where boaters will find provisions and services.

El Morro, a massive, Spanish fortress from the 16th century, is a major attraction and UNESCO World Heritage Site in San Juan. © istock.com / Martin Wheeler

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