Winter 2027 Caribbean cruises: tall ship sailing holidays aboard Royal Clipper, Star Clipper & Star Flyer — festive Caribbean & Panama Canal voyages.
Discover our Winter 2027/28 sailings with wind-guided itineraries blending classic clipper romance and private-yacht comfort. Enjoy westbound Atlantic crossings from Las Palmas or Lisbon, extended Christmas and New Year sailings from St John’s Antigua, and a scenic 9-night Panama Canal voyage from Colón to Puerto Caldera. Highlights include snorkeling and watersports at Tobago Cays, Isla Iguana, Coiba National Park and Parida Island; secluded beaches at Norman Island, Jost Van Dyke and Gustavia, St Barts; and reliable trade-wind passages through the Sir Francis Drake Channel. Perfect for holiday sailings, wildlife encounters and relaxed island-hopping aboard iconic tall ships.
