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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.

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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Yachtsman’s Caribbean
Flavors of the Caribbean

8 day, 7 night Yachtsman’s Caribbean cruise sailing roundtrip Philipsburg, St. Maarten aboard the tall sailing ship Wind Surf. Let us take you into hidden coves and tiny harbors no one else can reach as you fully experience the Caribbean’s private yachting scene. Explore the quaint island charm of Soper’s Hole and the inviting beaches of Jost Van Dyke as you overnight in the harbor. Sail to Virgin Gorda, with its assembly of house-sized rocks called The Baths. Savor the high life on St. Barts.

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Classic Caribbean
Classic Caribbean

8 day Classic Caribbean cruise sailing roundtrip Philipsburg, St. Maarten aboard the classic sailing ship Wind Surf. From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Here’s the best of the Caribbean in one single voyage.

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Jewels of the Windward Islands
Jewels of the Windward Islands

8 day Jewels of the Windward Islands Caribbean cruise sailing roundtrip Bridgetown Barbados aboard Wind Surf. This is the Caribbean of days gone by – deep blue waters, quiet coves, and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.

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