Summer in the Hamptons has a way of slowing time down — and we mean that in the best possible way. For both of us, it has always come back to a few simple things. Stopping at the ocean at least once a day, even in the off season — but summer makes it feel like a ritual worth protecting. Chasing sunsets that never get old no matter how many you've seen. Farmstand dinners in the garden, surrounded by hydrangeas in full bloom, where the evening stretches on longer than it should and nobody minds. Letting the kids stay up past their bedtime to roast marshmallows, because some things are worth the tired morning after.
And lately, exploring more by boat — finding the quiet of Shelter Island on a Tuesday afternoon, or hopping over to the North Fork for a glass of wine and a pace that reminds you what summer is actually supposed to feel like. The water changes everything out here, and once you find that rhythm, it's hard to want anything else.
This place has been our home, our work, and our favorite ongoing discovery for years — and it still surprises us. Every season brings something new to find, a new restaurant to love, a new corner of a familiar town that somehow escaped our attention. That's the thing about the Hamptons that's hard to fully understand until you've lived it: there is always more.
This guide is our attempt to hand you the version of the Hamptons we know — the one that takes a little longer to find, but stays with you long after you leave. We hope it helps you feel a little more at home out here.
Welcome to summer.
a note from Jenna & Joe Jenna
WELCOME TO The Hamptons
The Hamptons is not one place. That's the thing most people don't realize until they've spent real time here. It's a string of villages, each with its own personality, its own pace, its own reason to stay a little longer. Southampton has the grand estates and the kind of main street that feels like it was designed to be walked slowly. East Hampton is polished and particular.
Sag Harbor is the writer's town, the artist's town, the one that feels most like itself year-round. Amagansett is farm stands and sandy feet and nowhere else to be. And Montauk -- Montauk is the end of the road in the best possible way.
That range is what makes the Hamptons so endlessly interesting. There is genuinely something here for everyone, and the fun is in figuring out which version of it is yours.
There is no question that summer is why the Hamptons has the reputation it has. The energy is real. The restaurants are full, the beaches are alive, and there is always something new to discover. Every season brings new openings, new experiences, new reasons to explore -- and while that might draw the occasional grumble from longtime locals, I find it genuinely exciting. This place keeps evolving, and that's a good thing.
What I tell every client who comes out here for the first time: you cannot experience the Hamptons in a week. You certainly can't do it in a weekend. If you're here for a short stretch, you're either rushing or waiting in line -- and neither of those is the Hamptons I want you to know. The magic of this place lives in the laid-back weekdays. The Tuesday morning beach walk when the parking lot is empty. The Wednesday dinner reservation you actually got. The Thursday afternoon when the whole town feels like it belongs to you.
YOU CANNOT EXPERIENCE
THE
HAMPTONS IN A WEEK. THE MAGIC LIVES IN THE LAIDBACK WEEKDAYS.
This guide covers it all -- from Westhampton to Montauk, town by town, with the insider knowledge that only comes from actually living here. Consider it your shortcut to feeling like a local.
SUMMER HERE HAS A RHYTHM THAT FEELS BOTH RELAXED AND INTENTIONAL.
Westhampton Beach is often the first Hampton people fall for—and it makes sense. The drive from the city is shorter, the downtown is walkable and actually charming, and the restaurant scene rivals anywhere further east. You can park once, spend the day on Main Street, and never feel like you're missing something happening elsewhere. It's polished but unpretentious, and that balance is harder to find than you'd think.
Summer here has a rhythm that feels both relaxed and intentional. The beach is beautiful and less crowded than you'd expect, the farmers market on Saturday mornings draws locals and visitors alike, and you can build an entire day without getting back in the car. Whether you're here for a long weekend or just passing through on your way east, Westhampton Beach is worth the stop—and often, it's worth staying.
WESTHAMPTON BEACH
RESTAURANTS
Flora
One half of the sister restaurant duo on Main Street, Flora leans bright and coastal with a menu that changes seasonally. The cocktails here are exceptional—creative without being fussy—and the space feels like summer even on a cloudy day. Come for dinner and stay for drinks, or start here before exploring the rest of downtown.
Fauna
Fauna is Flora's moodier, more intimate sister. Same ownership, completely different vibe. The lighting is lower, the menu skews heartier, and the cocktail program is just as strong. If Flora is where you go to kick off the weekend, Fauna is where you settle in for a long dinner with friends. Both are worth visiting—they're that good.
Stone Creek Inn
Though technically in Quogue, it’s an institution that's been here long enough to earn its reputation. The setting is classic Hamptons—tucked away, surrounded by greenery, with a patio that fills up fast in summer. The menu is American with French influences, and everything feels carefully prepared without being overly precious. Make a reservation, especially on weekends.
Dockers Waterside Marina
Right on Dune Road between Westhampton & Hampton Bays with views that make you remember why you came to the Hamptons in the first place. Dockers is casual, family-friendly, and perfect for lunch or an early dinner when you want to be outside. The seafood is fresh, the atmosphere is relaxed, and kids are more than welcome. Go at sunset if you can.
THINGS TO DO BEACHWesthampton
Summer in Westhampton Beach centers around Rogers Beach, and for good reason. The sand is soft, the water is clean, and it's less crowded than you'd expect for how accessible it is. Parking requires a permit, but day passes are available at the village hall. Get there early on weekends—by mid-morning the lot fills up. Pack for the day and settle in. This is the beach that reminds you why you made the drive.
Beyond the beach, Westhampton Beach has a cultural side that surprises people. The Westhampton Beach Performing Arts Center hosts live performances all summer—concerts, plays, comedy shows, even film screenings. The venue itself is intimate and well-designed, and the programming is surprisingly strong. Check their schedule before your visit and plan an evening around it. It's a nice break from the usual dinner-and-drinks routine, and it gives the town a depth you don't always find in beach communities.
For golfers, The Country Club of Westhampton offers 18 holes surrounded by classic Long Island scenery—rolling greens, mature trees, water views. The course is well-maintained without being overly manicured, and it's not as well-known as some of the eastern clubs, which means it's often easier to get a tee time. Call ahead to check availability for nonmembers.
Main Street is small enough to cover in an afternoon but worth lingering in. There are independent boutiques, a good bookstore, coffee shops, and enough variety to make it feel like an actual town rather than a tourist strip. Saturday mornings, the farmers market sets up and draws a crowd—grab coffee and walk through. It's when Westhampton Beach feels most like itself.
Beach Bakery on Main Street is a Westhampton institution that has been doing things right since 1988. The fried croissants are the thing people come back for, the black and white cookies are a classic, and the peach pie -- featured on Food Network's Best Thing I Ever Ate -- is worth every bite. It's the kind of place that feels like it belongs to the town, because it does.
SMALL ENOUGH TO COVER IN AN AFTERNOON. WORTH COMING BACK TO ALL SUMMER.
Tucked into the village, Westhampton Beach Brewing Co. has become a summer afternoon anchor — local craft beers, a relaxed outdoor space, and a crowd that's more neighborhood than scene. It's where you end up at after the beach when nobody's ready to call it a day yet, and it earns its place on the list not because it's new, but because it consistently delivers exactly what it promises.
And new this summer: Pop Up Bagels opens June 5th at 130 Main Street, bringing their now-famous hot bagels to the East End for the first time. The concept is simple- small batches of hot bagels sold by the dozen, uncut, meant to be ripped apart and dipped into rotating schmears. Lines form early and sellouts happen fast. To mark the Westhampton opening they're partnering with Tate's Bake Shop on a limited-edition Chocolate Chip Cookie schmear. Worth the early arrival.
THE ONE THAT DOESN'T TRY TOO HARD... AND DOESN'T NEED TO.
HAMPTON BAYS
Hampton Bays sits at the western edge of the Hamptons, and it has always done things a little differently. The vibe here is genuinely relaxed -not curated relaxation, but the real kind. The kind where you can pull up to a waterfront restaurant in a cover-up, order something cold, and watch boats drift by without feeling like you're missing a reservation somewhere else.
What makes Hampton Bays worth knowing is its water. The town sits between the Atlantic Ocean and the Shinnecock Bay, which means you have options most other Hamptons villages don't -ocean beaches on one side, calm bay swimming and boating on the other. It's a place that rewards people who actually want to be on the water, not just near it.
The restaurant scene has grown into something worth the drive on its own. A handful of spots have figured out exactly what a summer waterfront meal should feel like -- easy, unhurried, with good food and better views. Come hungry and plan to stay longer than you intended.
RESTAURANTS
Rumba
Rumba is a favorite waterfront spot that earns its reputation every summer. It's lively without being chaotic, and the bar scene draws a crowd for good reason: the drinks are strong, the energy is right, and the views over the water make it easy to lose track of time. Come for dinner, stay for drinks, or arrive by Rum Barge if you're making a night of it.
Cowfish
Casual, waterfront, and consistently good: Cowfish is the spot you come back to because it never disappoints. The setting is relaxed, the seafood is fresh, and it has easy summer energy that's harder to find than it should be. It's also the other end of the Rum Barge route, which makes the whole evening feel like a bit of an adventure.
Amalfi
Amalfi is summer on a plate. The waterfront setting, the spritzes, the warm-weather Italian menu... it all adds up to exactly the kind of meal you want when the days are long and you're not in a rush. It leans into the season fully, and the atmosphere does most of the work. Go for dinner when the light is good and order something with bubbles.
Sundays on the Bay
The name tells you everything you need to know about the energy here. Sundays on the Bay is casual, welcoming, and genuinely family-friendly... the place where lunch turns into a long afternoon without anyone minding. The waterfront setting is relaxed, the menu is approachable, and kids are more than welcome. It's a good one to keep in your back pocket for the days when you want good food without any fuss.
THINGS TO DO Hampton Bays
Summer in Hampton Bays begins at the water and there's more of it here than almost anywhere else on the South Fork. The town sits between the Atlantic Ocean and the Shinnecock Bay, which means your options on any given day are genuinely different from each other. Ponquogue Beach is the ocean side: wide, clean, and surprisingly uncrowded for how good it is. Located on Dune Road, the sand is soft, the water is clear, and there's enough space to actually settle in. Parking requires a permit, but day passes are available. Get there early on weekends, by mid-morning the lot fills up.
On the bay side, Meschutt Beach is the one to know for families or anyone who wants a slower pace. The water is calm, there are picnic areas and volleyball courts, and the playground makes it easy to spend a full afternoon without anyone getting restless. It's also one of the best sunset spots on the East End. Bring a blanket and plan to stay for it.
Beyond the beaches, Hampton Bays is a boating town at its core. The canal runs right through the center of it, and getting out on the water here is easier and more accessible than almost anywhere else in the Hamptons. Rent a boat for the afternoon or charter one for the day. The views of the bay from the water are the kind that make the whole drive worth it.
WHERE THE CANAL MARKS THE BEGINNING OF SOMETHING DIFFERENT.
And if you're spending an evening on the water, don't miss the Rum Barge: a small boat that runs between two of the town's best waterfront restaurants all summer long. It's casual, a little festive, and turns dinner into something you'll actually talk about later.
For those who want to venture slightly beyond, the North Fork wine country is closer from here than from anywhere else in the Hamptons. More than 60 vineyards are spread across the farmland just across the bridge, and a half-day tasting trip is easy to build into a longer weekend. Go on a weekday if you can. The tasting rooms are quieter and the drive through the fields is worth it on its own.
HERE THE HAMPTONS FIRST MADE ITS NAME ...AND STILL EARNS IT.
Southampton is where most people picture when they think of the Hamptons, and it delivers on that image without apology. The estates are grand, the main street is genuinely beautiful, and the energy in summer is polished without feeling stiff. It's the kind of town that has been doing this long enough to know exactly what it is.
What sets Southampton apart is the combination of things it does well simultaneously. The beach is worldclass. The shopping on Job's Lane and Main Street rivals anything you'd find in the city. The restaurant scene is deep enough that you could eat somewhere different every night for two weeks and not run out of good options. And the cultural life, anchored by the Parrish Art Museum, gives the town a depth that pure resort destinations rarely have.
This summer, Southampton is also becoming the place to be after dark. New venues are rumored to be joining the scene, and the energy on a Friday or Saturday night has a different charge than it did a few years ago. It's worth paying attention to.
SOUTHAMPTON
RESTAURANTS
Tutto il Giorno
A Southampton institution that has earned its place on every short list. The Italian menu is simple and well-executed, the space is warm & elegant, and the crowd is the kind of mix that makes for good people-watching. It's the restaurant you bring people to when you want to show them what a Hamptons dinner actually feels like. Make a reservation.
El Verano
The margaritas here are the ones you'll still be thinking about at the end of summer. The chef's margarita in particular is worth the trip on its own. The food matches the drinks: bright, wellseasoned, and exactly right for a warm evening. It's festive without being loud, and the kind of place that puts you in a good mood the moment you sit down.
Bistro Été
Bistro Été has the feel of a restaurant that knows exactly what it wants to be and executes it beautifully. The menu is French-influenced and seasonal, the room is intimate, and the whole experience has a quiet confidence to it. One thing worth knowing: you can reserve your steak ahead of time, and when you walk in, you'll spot the named steaks waiting for their owners (Jimmy Fallon is a regular). Go for a special occasion or make it one, and book the steak when you reserve your table.
Saint Ambreous
Part café, part destination restaurant: Saint Ambreous is a Southampton ritual at any hour. The front is a classic Italian café with excellent coffee and pastries worth lingering over on a sunny morning. But walk through to the back and there's a full formal dining room that's one of the more elegant dinner experiences in town. Come early for a cornetto and coffee, or come back at night for something more. It rewards both visits.
THINGS TO DO Southampton
Southampton's summer begins at Coopers Beach, and for good reason. Consistently ranked among the best beaches in the country, the sand here is soft, the water is clear, and the setting, with its classic Hamptons dune backdrop, is exactly what you came for. Parking requires a permit or a fee, but it's worth it. Go early on weekends, and plan to stay.
For a quieter alternative, Coopers Neck Lane Beach offers calm bay water that's ideal for swimming, paddleboarding, or simply sitting with a book without the ocean crowd. It's the spot locals keep to themselves, which is reason enough to know about it.
Beyond the beach, Southampton is one of the best shopping destinations on the East End and it doesn't get enough credit for it. Job's Lane and Main Street are lined with independent boutiques, home stores, and a handful of welledited national names that feel at home here rather than out of place.
It's the type of shopping where you go in for one thing and come out with a bag and a plan to come back. Set aside a morning, grab a coffee, and walk slowly.
The Parrish Art Museum is a genuine cultural anchor for the entire East End. The building itself, designed by Herzog and de Meuron, is worth seeing on its own, but the collection inside, focused on American art with a particular emphasis on East End artists, gives it real substance. Check the schedule before you go. The programming throughout the summer is consistently strong.
BREATHTAKING NATURAL BEAUTY AND UNPARALLELED TRANQUILITY
For something more restorative, Shou Sugi Ban House in neighboring Water Mill is the Hamptons' first destination spa and wellness retreat, and one of the most thoughtfully designed wellness experiences in the region. Set on five acres of serene grounds, it offers everything from therapeutic massage and hydrotherapy to yoga, sound baths, and a culinary program designed by a Michelin-starred chef. Day guests can book a package with a two-service minimum. During peak season, reserve at least three weeks out.
And this summer, Southampton's nightlife is worth watching. Maison Close is joining the scene, and there are strong rumors that Common Ground will make an appearance. If the evenings here have felt quieter than you'd like in past summers, that may be changing.
And if you want to ease into the night, Calissa is the move: a Greek restaurant with genuinely delicious food that slowly transforms into something closer to a nightclub as the evening goes on. Start with dinner, stay for the energy.
SOUTHAMPTON Bay Side
We discovered 41 Indian Road in Southampton on a quiet Tuesday morning, and the first thing you notice is the stillness. Set on a private, gated half-acre surrounded by mature specimen trees and sculptural gardens, this five-bedroom Arts & Crafts modern sits just 500 feet from Towd Point: one of Southampton's most genuinely beloved waterfront spots. The cedar shingle exterior, covered porches, and floor-to-ceiling glass doors manage to feel both architectural and completely at ease. Inside, the open kitchen, dining, and living areas flow together the way a summer house should: effortlessly.
The real draw is what's just outside the gate. Towd Point offers calm bay waters, a sandy shoreline, paddleboarding, kayaking, and sunsets that make you stop midsentence. No ocean beach crowds, no scramble for parking...just a quiet, protected stretch of waterfront that Southampton residents genuinely treasure.
THE ONE THAT QUIETLY HOLDS THE BEST OF EVERYTHING TOGETHER.
Bridgehampton sits at the center of the Hamptons in every sense: geographically, culturally, and in terms of what a summer day here can actually look like. It doesn't have the shopping scene of Southampton or East Hampton, but it's quietly become the fitness and wellness center of the East End — The Barn and Equinox are both here. The farms are right there. The wineries are right there. The beach is wide and beautiful and a little less crowded than it should be given how good it is.
What you notice when you actually slow down here: a general store that doubles as a post office, a sixth-generation farm that makes its own spirits, vineyards that have been here long enough to have real character. It's a town that rewards the people who aren't just passing through.
BRIDGEHAMPTON
RESTAURANTS
Almond
A Bridgehampton staple with the kind of warm, unpretentious energy that makes you want to come back. The food is consistently good, the room feels lived-in in the best way, and the martinis are exceptional (order one before you even look at the menu). It's the kind of restaurant that locals actually go to, which tells you everything.
Elaia Estiatorio
Authentic Greek done right. The move here is to order a Greek white wine, something crisp and mineral, and then fill the table with small plates to share. The mezze format turns dinner into an event, and the food rewards that approach. Go with people you like to linger with.
Bobby Vans
A classic Bridgehampton steakhouse that has been here long enough to have earned its reputation. The room has the kind of old-school confidence that only comes with time, and the steaks are exactly what they should be. This is the dinner you want after a long beach day when you're ready for something substantial.
Bridgehampton Inn & Restaurant
This one flies under the radar, which is part of what makes it worth knowing. The atmosphere is cozy and genuinely charming, the cocktails are creative without being precious, and the fried artichokes are the dish I keep coming back for. It feels like a find even after you've been going for years.
THINGS TO DO Bridgehampton
Start at Sagg Main Beach: a lifeguarded stretch with stunning ocean views that manages to feel a little more local than some of the more well-known beaches further east. Ocean Road Beach is the quieter alternative, with minimal parking that keeps the crowds down naturally. Both are worth knowing.
Then there's the Sagaponack General Store, which I'll admit I'm not usually one to chase viral moments, but this one earns every bit of attention it gets. The cookies are genuinely exceptional, the charm of the place is undeniable, and most people don't realize it's also a fully functioning U.S. Post Office. It's the stop that turns into a story you tell people later.
For wine, Bridgehampton is the place. Wölffer Estate Vineyard is the most famous vineyard on the East End and home to Summer in a Bottle: the rosé that has become synonymous with Hamptons summers. The main tasting room requires a reservation, but the wine stand is more casual and doesn't. Friday nights bring live music, which makes it one of the better summer evenings you can plan without much effort.
Channing Daughters is the smaller, more intimate counterpart. Bring a blanket, sit in the garden, and try the smaller-batch wines that you won't find anywhere else. It feels like a discovery even if you've been before.
For something a little different, Sagaponack Farm Distillery is a seed-to-glass spirits operation on a sixth-generation family farm just minutes from Bridgehampton. The tasting room is tucked into a 1930s farmstead, private and unhurried, with award-winning estategrown spirits made from crops grown on the same land. The potato vodka and the bourbon are both worth trying. It's open year round and makes for an interesting afternoon.
THE FARMS ARE RIGHT THERE. THE WINERIES ARE RIGHT THERE. AND THE BEACH IS WIDE AND BEAUTIFUL AND A LITTLE LESS CROWDED THAN IT SHOULD BE.
New this summer, Nourish by the Round Tree just opened in Bridgehampton and is already worth paying attention to. Chef Dewa Wijaya, Bali-born, classically French-trained, and formerly Executive Chef at COMO Shambhala Estate, is cooking a menu rooted entirely in East End farms and fishermen, with Balinese influences woven through.
The space seats 120 across a main dining room, a bar, and an outdoor garden patio. It's dinner nightly through August, and the type of opening that doesn't come along every summer.
A WORKING HARBOR, A REAL MAIN STREET, AND A RHYTHM ALL ITS OWN.
SAG HARBOR
Sag Harbor operates on its own terms, and that's exactly why people love it. The main street is genuinely beautiful, historic architecture, independent shops, a working harbor lined with sailboats and yachts, and the energy here has a creative, unhurried quality that feels different from the rest of the Hamptons. Writers, artists, and people who have been coming for decades all end up here eventually. It has that effect.
What makes Sag Harbor worth a full day (or a full summer) is the layering of it. The cultural life is real, anchored by Bay Street Theater and a gallery scene that takes itself seriously without being precious about it. The restaurant scene punches well above its size. And the harbor itself, with boats coming and going all day, gives the whole place a rhythm that's hard to find anywhere else on the East End.
RESTAURANTS
Lulu Kitchen and Bar
From the team behind the legendary Duryea's, Lulu brings that same instinct for a great waterfront experience to Sag Harbor. The food is fresh and well-executed, the room has energy without being loud, and the setting makes it easy to lose track of time in the best way. A strong addition to the Sag Harbor dining scene from a group that knows exactly what they're doing.
Bell & Anchor
Order the bouillabaisse. That's the short version. The longer version is that Bell & Anchor is a consistently excellent waterfront restaurant with a menu that takes its seafood seriously and a room that feels right for both a casual dinner and a special occasion. The bouillabaisse is the dish that earns its reputation every time.
Beacon
From the same restaurant group as Bell & Anchor, Beacon is the one you go to when the sunset matters as much as the meal. The waterfront setting is more open and scenic, the menu is equally strong, and timing your reservation for the light is worth the planning. Go for dinner and stay for the view.
Sen
The best sushi on the East End, and it's not particularly close. Sen has been the standard for Japanese dining in the Hamptons for years, and it holds that position without much effort. The fish is impeccably fresh, the room is calm and considered, and it's the kind of meal that travels well: meaning you'll still be thinking about it on the drive home.
THINGS TO DO Sag Harbor
Long Beach is a long stretch of bay beach — calm water, kite surfers, sailboats drifting across. Havens Beach is smaller and more tucked away, with picnic areas and views of Shelter Island and Gardiner's Bay that are genuinely worth sitting with.
Bay Street Theater is one of the cultural anchors of the East End: a proper regional theater that programs live music, plays, and comedy throughout the summer. Check the schedule before you go and plan a night around it. Owned by Julia Andrews daughter, it gives you an evening that reminds you why summer out here is different.
For something new this summer, Hill House just opened in Sag Harbor and it's already worth a stop. The blue Dutch door and window seats give it an immediate charm, and inside there's a full Nell's Pick 'n' Mix candy wall...a detail that makes a shop feel like a destination rather than just a store. It carries Hill House Home's fashion and home collections alongside the candy bar, and the whole thing has an energy that's hard to walk past without going in.
And then there's Babe's Diner: small and it fills up fast because the food is genuinely good and the room only holds so many people (8 to be exact). Go early, plan for a wait, or order to go.
For one of the more memorable ways to experience the harbor, YachtHampton's Dock & Dine program is worth knowing about. The concept is simple and exactly right: they secure your reservation at waterfront restaurants across the Hamptons, Shelter Island, and the North Fork, and you arrive by boat. The concierge handles the reservation, the captain handles the rest. It turns dinner into an experience that's hard to replicate any other way.
THE HARBOR GIVES THE WHOLE PLACE A RHYTHM THAT'S HARD TO FIND ANYWHERE ELSE ON THE EAST END.
And if you find yourself wanting more of that, more mornings on the water, more evenings arriving somewhere by boat, YachtHampton's FleetShare Membership is worth a serious look. It's the answer to wanting a full boat life without the cost, maintenance, and responsibility of owning one.
Members get access to the full fleet any time, priority reservations during peak season, a dedicated concierge for every excursion, and assigned crew on every journey. For anyone spending real time in the Hamptons this summer, it's one of those things that changes how the whole season feels.
Tucked into a quiet half-acre in Sag Harbor, this modern-traditional home was designed for the way people actually want to spend their summers. Close to Peconic Bay, unhurried by nature, and finished with every detail that makes a house feel like a real escape.
THE VERSION OF SUMMER WHERE YOU STOP KEEPING TRACK OF TIME AND JUST LIVE IT
84 Wildwood Drive opens the way a good summer should — an easy flow from kitchen to covered porch, dinner outside more nights than not, and a heated saltwater pool that becomes the center of every afternoon. The cabana has a TV for the days nobody wants to move. There are bikes in the garage for the mornings when everyone does. Outdoor lighting and heating keep the evenings going long past when they should.
Five en-suite bedrooms hold a full house without feeling crowded. A separate media room gives the kids their own world. Peconic Bay access means the water is always an option — and out here, the water is always the right answer.
Inquire for details.
UNHURRIED BY DESIGN AND WORTH EVERY MINUTE IT TAKES TO GET HERE.
SHELTER ISLAND
Shelter Island sits between the North and South Forks, reachable only by ferry, and that small inconvenience is part of what makes it what it is. The people who make the crossing tend to be the ones who actually want to be there, which gives the whole island a different quality than the rest of the Hamptons. It's quieter, greener, and genuinely slower -- not as a pose, but as a fact of geography.
What's happening on Shelter Island this summer is worth paying attention to. The restaurant scene has matured into something that can hold its own against anywhere on the East End, the waterfront dining is some of the best in the region, and the ferry connection to Greenport makes it easy to build a full day that moves between two completely different worlds.
RESTAURANTS
Léon 1909
A daughter-father project that has become one of the most talked-about restaurants on the East End since it opened in 2022 and for good reason. The setting is warm and considered, anchored by a wood-burning hearth, and the menu is Provençal French-Italian with a focus on regional ingredients and unfussy, seaside cooking. It's the kind of restaurant that feels like it belongs exactly where it is. Open Friday through Sunday evenings. Reserve well ahead.
The Terrace at The Pridwin
Dining overlooking Crescent Beach with a cocktail program from Dante. That combination alone is worth the trip. The setting is genuinely beautiful, the drinks are exceptional, and the whole experience has the kind of easy elegance that Shelter Island does better than almost anywhere. Go for sunset and let the evening unfold from there.
Rams Head Inn
The setting alone, a classic inn on the water that looks like something out of a film, would be enough to put it on the list. But this summer there's a real reason to go back even if you've been before: new chef Jessica Taccone has taken over the kitchen with a hyper-local, from-scratch approach that's already generating attention. The menu changes monthly, she's making her own butter on premise, and the whole thing has the energy of a kitchen that's genuinely excited about what it's doing. The scene here has always been something out of a dream and now the food is catching up.
Marie Eiffel
A small market right in Shelter Island Harbor that operates as a café, a deli, and a local institution all at once. The crab cake sandwiches and lobster rolls are the things to order: fresh, well-made, and exactly right for eating at the picnic tables overlooking the water. It's casual and unpretentious and completely satisfying. Don't overthink it.
THINGS TO DO Shelter Island
Crescent Beach is the anchor: a calm, beautiful stretch of water that faces west and catches the afternoon light in a way that makes it hard to leave. It's the beach that rewards people who show up without a plan and stay longer than they intended.
Shelter Island is also genuinely good sailing territory, with calm protected waters that make it accessible whether you're experienced or just getting started. Getting out on the water here, even for a few hours, changes how the whole island feels.
Sunset Beach starts as a dinner destination and gradually becomes something else entirely as the evening goes on. The setting is iconic: built into a majestic tree, right on the water and the mojitos are famous for a reason. Come for dinner, stay for the party. It's one of those summer evenings that's hard to replicate anywhere else.
And one of the more underrated moves from Shelter Island: walk on the North Ferry to Greenport. It's a short crossing and you land directly in the heart of one of the most charming small towns on the East End... independent shops, excellent restaurants, a working waterfront, and a completely different pace. It makes for an easy half-day that feels like a real departure without going very far at all.
THE PEOPLE WHO MAKE THE CROSSING TEND TO BE THE ONES WHO ACTUALLY WANT TO BE THERE. THAT MAKES ALL THE DIFFERENCE.
If you want to get on the water without a boat of your own, Shelter Island Kayak Tours offers guided and self-guided paddling through the calm, clear waters of West Neck Harbor and Coecles Harbor: past ice-age boulders, protected woodlands, and wetlands that look completely different from the water. The Coecles Harbor Marine Water Trail is a fivemile interpretive paddling route worth the full loop if you have the time.
MashomackPreserve covers nearly a third of the island and offers over 11 miles of trails through oak woodlands, tidal creeks, freshwater marshes, and coastline managed by The Nature Conservancy. Admission is free, more than 200 bird species have been recorded here, and it earns a full morning without asking for anything in return.
FOR KIDS& Families
The Hamptons is genuinely great with kids, you just have to know where to point them. Beyond the beach, which sells itself, there's enough here to fill a whole summer of mornings and afternoons without repeating yourself once.
Amber Waves Farm in Amagansett is the kind of place that makes kids feel like they're actually doing something real. Harvesting vegetables, feeding animals, learning where food comes from in a way that sticks. Educational programs and workshops run all summer, and it's the family heart beat of The Hamptons.
The South Fork Natural History Museum in Bridgehampton is worth an afternoon, especially for younger kids. The touch tank alone makes it worth the trip: hands-on with local marine life in a setting that's engaging without feeling like a school field trip. A great option when the beach isn't calling.
For something a little quieter, Madoo Conservancy in Bridgehampton partners with the Hampton Library for storytime in the garden during the summer months. It's a beautiful, tucked-away spot that most visitors never find, and a lovely way to spend a slow morning with little ones.
Older kids have their own list. The Montauk Point Lighthouse is a must. Climb to the top, take in the views, let the history land a little. The skate park in Montauk will keep a certain kind of kid busy for an entire afternoon.
Deep Hollow Ranch offers guided trail rides through the dunes and along the beach that are hard to forget. And if there's a wanna-be surfer in the family, get them a lesson at Ditch Plains. They'll spend most of it underwater and love every minute of it.
For a summer evening the whole family will talk about, make the trip to The Pridwin on Shelter Island for their Wednesday Night BBQ. It's been a Shelter Island tradition for over 60 years: allyou-can-eat cookout on the water-view lawn, communal picnic tables, live music, and a sunset over Crescent Beach that earns its reputation every single week.
THE HAMPTONS IS GENUINELY GREAT WITH KIDS. YOU JUST HAVE TO KNOW WHERE TO POINT THEM.
Kids have the run of the place while parents actually get to sit back and relax. It runs Wednesdays at 5:30pm from June through late September. Buy tickets in advance; it fills up.
WHERE THE HAMPTONS LIVES UP TO EVERY VERSION OF ITSELF.
EAST HAMPTON
East Hampton has been doing this since 1648, and it shows — in the architecture, the main street, the beaches, and the way the whole town carries itself with an unhurried confidence. It's polished without being stiff, beautiful without being showy, and busy in summer without ever quite losing the thread of what makes it worth coming to.
The range here is part of what makes it work. You can spend a morning at one of the best beaches in the country, an afternoon moving between Chanel and a family-run shop that's been on Newtown Lane for decades, and an evening at a restaurant that could hold its own in any city. East Hampton doesn't ask you to choose a lane — it just gives you a lot of good ones.
RESTAURANTS
Bostwick’s
Two locations, two completely different experiences. Bostwick's Chowder House on Pantigo Road is the casual, no-reservations seafood staple: hot lobster rolls, fish tacos, and a laid-back patio that's exactly right for a summer lunch. Bostwick's on the Harbor in Springs is the same team with a waterfront setting on Three Mile Harbor that ranks among the best views in the Hamptons. Arrive at 4:30, order oysters, and let the evening come to you.
Blue Parrot
A tiny Mexican spot tucked down an alley, with a crowded bar and a long time East Hampton favorite. Order the shrimp or lobster tacos, and approach the Dirty Bird margarita with appropriate caution. Grab an outdoor table if one opens up — worth the wait. Open for lunch and dinner.
LDV at the Maidstone
Set inside the historic Maidstone Hotel on Main Street, LDV brings Italian coastal cooking to one of East Hampton's most beautiful settings. Chef Jorge Espinoza, formerly of Scarpetta, built a menu around crudos, fresh pasta, local oysters, and grilled seasonal produce that evokes an Italian summer. Dinner Wednesday through Sunday, brunch on Sundays. Reserve ahead.
Wayan and Ma.dé
Two celebrated Indonesian-French concepts from Cédric and Ochi Vongerichten, set together at EHP Resort and Marina on Three Mile Harbor. The food is vibrant and transportive, lobster noodles with black pepper butter, soy-tamarind glazed ribs, handcrafted cocktails with infused liquors and exotic ingredients, all against an open-air harbor backdrop. It's a dinner that feels like a real departure, and one of the more exciting things happening in East Hampton this summer.
THINGS TO DO East Hampton
Start the morning at Grindstone Coffee and Donuts on Race Lane: small-batch brioche and cake donuts with rotating seasonal flavors, strong coffee, and a back patio that makes it easy to linger longer than you planned. Go early, the good flavors go fast.
Main Beach is the anchor of any East Hampton summer. Consistently ranked among the best beaches in the country, with wide sand and clean water that earns its reputation every year. The Beach Hut is right there for food and drinks, and on Tuesday evenings through the summer the beach hosts Tuesdays at Main: an oceanside concert worth planning your nigth around.
Maidstone Park Beach is a different kind of experience entirely. A calm bay beach with sunset views that locals have claimed as their own. A new playground was just installed this summer, and on warm evenings you'll find families set up with grills, fire pits, and s'mores while the kids run well past their bedtime.
It's a scene out of a summer movie that doesn't get talked about much, which is exactly what makes it worth knowing.
For paddleboarding and kayaking, Springs has some of the most beautiful calm-water spots on the East End. Louse Point, Gerard Drive, and Maidstone Park are all protected, scenic, and places that feel like a local secret even when they're not. Get out early before the wind picks up and the water is glassy.
WHERE A PERFECT HAMPTONS DAY ACTUALLY COMES TOGETHER.
East Hampton's shopping is one of its most underrated pleasures, and Newtown Lane gives you the full range without having to work for it. Chanel and Prada sit comfortably alongside shops that have been here for decades and have no intention of leaving. Breezin’ Up is the one to know: a family-run shop since 1998, selling soft, easy coastal clothing that feels made for exactly this place.
After a morning of shopping, Carissa's is the natural place to land. A James Beard-nominated bakery with two East Hampton locations. The Newtown Lane spot is a quick takeout in the heart of the village, perfect between shops, while the Pantigo Road location is the fuller experience: European-style breads, vibrant pastries, signature sandwiches, and a sunny outdoor garden worth sitting in.
FARM STANDS, SANDY FEET, AND LUNCH ON THE STRETCH. THIS IS SUMMER.
Amagansett sits just east of East Hampton and operates at a slightly different frequency — a little looser, a little less curated, with a main street that still has the feel of a town that knows what it is. The square is the center of it, ringed with restaurants, shops, and foot traffic that makes for good peoplewatching on a summer afternoon. But Amagansett rewards the people who wander a little further — down to the beach, out to the farm, into the spots that don't advertise themselves.
This summer there are a few new reasons to pay attention. The food scene here has always punched above its size, and what's opening this year only adds to that.
AMAGANSETT
RESTAURANTS
Il Buco Al Mare
The Hamptons outpost of the beloved il Buco family, inspired by their sister restaurant in Ibiza and rooted in the same ingredient-driven philosophy. Ancient grain focaccias, imported tinned fish from the Iberian Peninsula, local seafood from the wood-burning oven, and a wine list focused on small coastal producers. A meal that feels like a real departure: unhurried, considered, and exactly right for a summer evening in Amagansett.
The Meeting House
Tucked into Amagansett Square and open Wednesday through Saturday evenings, The Meeting House is the dinner you plan ahead for. The room is warm and intimate, the cooking is thoughtful and seasonal, and the whole experience has a quiet confidence that makes it one of the more reliable spots on the East End.
The Clam Bar
A Hamptons institution that has been doing this long enough to know exactly what it is. The lobster rolls and clam chowder are the things to order, the outdoor picnic tables are the place to be, and the line is worth it every time. If you’re solo or a pair, sit at the counter. Go early or go late: the middle of the day in peak summer is not for the impatient.
Doubles
A neighborhood spot that Amagansett does better than most places... casual, consistent, and genuinely good. It's the dinner you don't overthink, the lunch that hits exactly right, and the place locals keep coming back to because it never lets them down.
THINGS TO DO Amagansett
Atlantic Avenue Beach is the anchor of any Amagansett summer: wide, open ocean, and in late summer one of the best spots on the East End for whale watching. There's something about seeing a whale breach just offshore on a quiet August afternoon that makes everything else feel small in the best way.
Napeague Beach is a different world entirely... calmer, more tucked away, with a quality that makes you feel like you've found something. The water is quieter, the crowd is thinner, and the whole stretch has an unhurried energy that's hard to find once July hits.
And sitting right on Napeague Harbor is theArt Barge: a retired WWII Navy barge beached on the shore that has been an art school and studio since 1960, originally founded as a summer outpost of MoMA.
Classes and workshops run throughout the summer for all levels, from open studio sessions for working artists to more structured programs... all set against the backdrop of the harbor and the surrounding natural preserve. It's an “onlyin-the-Hamptons” place that rewards the people who know to look for it.
Amber Waves Farm on Main Street is a place that works for everyone: kids running through the fields, adults loading up at the market, and anyone in between just happy to be somewhere that feels genuinely alive. It's a nonprofit teaching farm now in its 17th season, with 30 acres of production, a market stocked with 500 varieties of vegetables, fruits, herbs, and flowers, and a kitchen open daily for breakfast and lunch. It always turns into a longer visit than you planned, and that's exactly the point.
AMAGANSETT REWARDS
THE
PEOPLE WHO WANDER A LITTLE FURTHER.
For a slice between beach and dinner, Fini Pizza on Main Street is the move: a NYC import that has found a natural home in Amagansett. The pizza is simple and well-made, the Italian ice is worth adding, and solves the "what do we do between 3 and 7pm" problem without any effort. (Also great for a late night slice after The Talkhouse.)
On summer afternoons, the Shark Bar is where Amagansett comes alive. Live music runs throughout the season (including performances from Joe) and the energy is exactly what a summer afternoon should feel like. It's casual, it's fun, and it's the kind of place that turns into a longer evening than you intended.
HOW TO DO The Hamptons
The single most important thing I tell every client before they arrive: give yourself the weekdays. The Hamptons on a Tuesday is a completely different place than the Hamptons on a Saturday. The restaurant you couldn't get into all weekend has tables on Wednesday. The beach parking lot that's full by 9am on Saturday is empty on a Monday morning. Weekdays are not the consolation prize, they are the whole point. And worth knowing: Thursday is the new Friday now. Traffic from the city starts getting heavy Thursday afternoons, so plan your arrival accordingly.
Think in off-times always. Early morning and late afternoon are when this place is at its best. Build your days around that rhythm and you'll leave feeling like you actually lived here rather than just visited. Start mornings at Round Swamp Farm before the day gets away from you. Order your staples from FreshDirect before you arrive, then get everything fresh from the farm stands once you're here. The produce is genuinely better and it's the right way to shop out east.
Make reservations earlier than you think you need to, always have a backup, and if you don't have a parking sticker, download the Ride Circuit app: free rides from town to the beach, and not enough people know it exists.
Most importantly, spend your money locally whenever you can. The farm stands, the independent shops, the family-run restaurants that have been here for decades. They're what make this place worth coming back to.
Nightlife
The highest concentration of late night energy is in Montauk. That's just the reality. But there are great spots throughout the Hamptons worth knowing about. A few things to keep in mind: towns are spread out, so don't plan on jumping between them in one night. Daytime parties and sunset are very much a vibe out here. New places pop up every summer, these are the ones that have earned theirplace:
THROUGHOUT_THE_HAMPTONS
Stephen_Talkhouse: Amagansett's legendary live music venue. Still the best.
Mason_Close: Southampton's answer to a proper night out.
SiSi: Increasingly known for party brunch and late afternoon vibes. Reggae on Sundays.
Murf]s: Small tavern in Sag Harbor that often has a line out the door. Beware the dart board when you walk in.
Ketchy_Beach: This year showing up on 3 Mile Harbor in East Hampton
Calissa: Greek restaurant in Watermill. Turns into a party after dinner.
MONTAUK
Surf_Lodge: Daytime party on the water, then the crowd moves east.
Montauk_Project: Where the Surf Lodge crowd ends up.
Bagatelle: Daytime party.
Bar_Lalo:_New this summer, late night vibes, worth watching.
Bounce_Beach: Exactly what it sounds like. A scene.
The_Point: A Montauk late night staple.
Mary_Lou]s: Delicious cocktails.
Montauket: Perfect Sunset. Line out the door on weekends
Memory_Motel: Unassuming until you get inside.
Shagwong: Late night.
THE END. AND EVERYTHING THAT COMES WITH IT.
MONTAUK
Montauk operates by its own rules. It's the furthest east you can go, and it feels like it. The lighthouse, the surfers at Ditch, the fishing boats coming in at dawn, the smell of salt air before the rest of the world wakes up. Yes, there's a party scene, but Montauk was a fishing town long before it was a destination, and that identity is still very much alive if you know where to look. Fresh seafood for dinner, a sunset over Fort Pond Bay, a morning on the beach that feels like it belongs to you. That's the Montauk worth knowing.
One thing worth knowing before you go: Montauk has over 55 restaurants. This is not a comprehensive list. It's a short one of the places worth planning around.
RESTAURANTS
Duryea’s Lobster Deck
The lobster deck that became a legend. Clipboard orders at a cashier window, the freshest seafood on the East End, and a setting that makes time feel like it's standing still. The lobster cobb gets the hype but I prefer the tuna crudo, raw bar and skirt steak for variety. The whole experience has a nostalgic, rosé-soaked quality that's impossible to replicate. New this season: Duryea's Sunset Scoops.
Inlet Seafood
Straight off the docks and onto your plate. Inlet is where you go when you want the real Montauk, no pretense, just exceptionally fresh fish in a setting that reminds you exactly where you are. The fishermen who caught your dinner probably just walked past your table.
Mostrador Marram
The Montauk outpost of the legendary Uruguayan restaurant concept from chef Fernando Trocca and restaurateur Martin Pittaluga. The same team behind La Huella in José Ignacio, one of the most celebrated beach restaurants in the world. The menu changes daily based on what's seasonal and local, the vibe is flip-flops-welcome, and the food makes you feel like you're somewhere far more exotic than Long Island. Breakfast, lunch, and dinner, steps from the Atlantic.
The Dock
A proper fisherman's dive: no frills, no reservations, no pretense. The lobster roll here is one of the best on the East End, and the specials menu is always where the real action is. Whatever the boats brought in that morning is what you're ordering. It's the place that doesn't need to advertise itself, and hasn't for decades.
THINGS TO DO Montauk
Ditch Plains is the anchor of any Montauk morning. The waves here are consistent enough to draw serious surfers from around the world, and even if you never get in the water, watching them from the beach is its own kind of entertainment. Surf lessons are available for all levels: one of those experiences worth doing at least once, even if you spend most of it underwater.
Hooked is the move when you want to eat well without table service.. Grab a chowder and a lobster roll, walk straight to the beach, and call it the perfect Montauk lunch. No table, no wait, no problem.
Gosman's is one of the great Montauk institutions, and this summer it gets a proper refresh. The new Lobster House & Clam Bar debuts for the 2026 season, inspired by the beloved former Inlet Café and Clam Bar, with fresh seafood sourced right from the docks, lobster tacos, pan-seared tuna, and mussels in white cream sauce.
You can dine waterside or order at the window. Topside Bar is back as well. It's been a Montauk fixture for over 80 years for a reason and our favorite stop for some clams and a corona after the beach.
The Montiki is the catamaran-style boat charter that makes a Montauk afternoon feel like a different kind of trip entirely. Sunset cruises, party charters, or just a few hours on the water... one of the better ways to see Montauk from the outside in. A lot of our favorite summer memories are on the MonTiki.
THE FURTHEST EAST YOU CAN GO. AND SOMEHOW, STILL WORTH EVERY MILE.
The Montauket is the local's version... a no-frills bar perched above the water with some of the best sunset views on the East End. Go on a weekday. The parking is easier, the crowd is thinner, and the whole thing feels more like the Montauk that people who actually live here know.
For sunsets, Montauk delivers in two very different ways. Navy Beach sits on 200 feet of private beach on Fort Pond Bay, with unobstructed water views and an atmosphere that makes you want to stay well past dark. Toes in the sand, a drink in hand, and a sky that earns its reputation every evening.
MAKING THE HAMPTONS PART OF your story
Real estate, for us, has always been about more than a transaction. It's about helping people find their place in the Hamptons — in whatever way that looks right now.
Maybe you're renting for the summer and starting to wonder what it would feel like to stay. Maybe you've been coming here for years and something is starting to shift. Maybe you're not ready for anything yet, and you're just here for the season, letting it do what it does.
All of that is a beginning.
We're locals, and we've watched this place become part of people's stories in ways they didn't always plan for. A summer that turned into a tradition. A rental that turned into a search. A search that turned into home. We're here for wherever you are in that arc — no rush, no pressure, just a genuine love for this community and the people who find their way to it.
When the time feels right, we'd love to be part of what comes next.
