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Caribbean Small Ship Cruises

Caribbean Cruises

No long lines at the buffet, no bingo, no belly flop contests here. These Caribbean cruises are packed with rich experiences, history, culture and adventure.

Featured Itinerary

The Hidden Caribbean: Exploring the Yachtsmans Grounds of the U.S. & British Virgin Islands

This is a cruise to the unspoiled Caribbean, calling at small islands that are beyond the reach of the mega cruise ships and where there is a noticeable absence of grand resort development. Aboard the intimate cruise ship Yorktown, you'll sail leisurely through idyllic islands that appear as a series of green jewels strung on the necklace of an incredibly blue sea. Yorktown allows access into secluded bays, coves, and marinas, and the small number of guests it accommodates. Swim right off the ship and snorkel in some of the clearest waters imaginable, where coral, colorful reef fish, and other fascinating marine life thrive. Relax on palm-lined, white-sand and uncrowded beaches, and explore the natural beauty of these seldom-visited islands on hikes and organized shore activities. Meet with the friendly local inhabitants, and learn from our onboard team of naturalists and other experts.

Hidden Caribbean: Exploring the Yachtsmans Grounds of the U.S. & British Virgin Islands

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Caribbean Cruise Itineraries

Sailing the Caribbean aboard Sea Cloud
Sailing the Caribbean aboard Sea Cloud

8 day, 7 night Caribbean cruise sailing the Caribbean Sea aboard the luxurious sailing ship Sea Cloud. This Caribbean vacation differs greatly from the run-of-the-mill, tourist-laden experience. For this Caribbean adventure travel cruise, simply fly to Bridgetown, Barbados and set foot aboard the legendary Sea Cloud — the world’s most elegant square-rigged tall ship, carrying just 58 guests.

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The Hidden Caribbean
The Hidden Caribbean: Exploring the Yachtsmans Grounds of the U.S. & British Virgin Islands

8 day, 7 night The Hidden Caribbean cruise, sailing roundtrip from St. Thomas aboard Yorktown. Explore the Yachtsmans Grounds of the U.S. & British Virgin Islands, cruising to the unspoiled Caribbean, calling at small islands that are beyond the reach of the mega cruise ships and where there is a noticeable absence of grand resort development.

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West Indies Expedition
West Indies Expedition

7 day, 6 nights West Indies Carribean expedition cruise sailing from La Romana, Dominican Republic to Bridgetown, Barbados aboard Silver Explorer. This Caribbean West Indies adventure features Tropical rainforests, native archaeological digs, and restored sugar mills.

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Caribbean Sea Adventure
Caribbean Sea Adventure

9 day, 8 night Caribbean Sea Adventure sailing from Bridgetown, Barbados to Colon, Panama aboard Silver Explorer. On this Caribbean expedition cruise, you'll experience the Caribbean, it's culture, history and nature, like no mega-ship can.

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