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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

Lindblad Expeditions, in partnership with National Geographic8 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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Classic Caribbean
Classic Caribbean

Windstar Cruises8 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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Antilles Island Hopping
Antilles Island Hopping

Windstar Cruises8-day Antilles Island Hopping Caribbean cruise sailing between Bridgetown to San Juan, Puerto Rico aboard Star Legend. Trade your down-filled comforter for a bright beach towel during this weeklong cruise up the Windward and Leeward Islands from Bridgetown, Barbados to San Juan, Puerto Rico. Whether you’re eager for new adventures or simply want a relaxing beach and a rum punch, this journey melts winter doldrums.

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Windward Islands Surf & Sunsets
Windward Islands Surf & Sunsets

Windstar Cruises8-day Windward Islands Surf & Sunsets Caribbean cruise sailing roundtrip San Juan, Puerto Rico aboard Star Pride. Revel in eight days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations.

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San Juan & the Virgin Islands
San Juan & the Virgin Islands

Windstar Cruises8-day San Juan & the Virgin Islands Caribbean cruise sailing roundtrip San Juan, Puerto Rico aboard Star Pride. Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike.

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Winter Antilles Escape
Winter Antilles Escape

Windstar Cruises8-day Winter Antilles Escape cruise sailing between San Juan to Bridgetown aboard Star Pride. Uncurl your frozen toes as you escape the winter doldrums during this week-long cruise featuring sundrenched beaches and steamy tropical rainforests along the Lesser Antilles Islands in the Caribbean.

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Yachtsman’s Caribbean
Flavors of the Caribbean

Windstar Cruises8 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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Best of the ABC Islands
Flavors of the Caribbean

Windstar Cruises8 day Best of the ABC Islands cruise sailing Bridgetown to Oranjestad aboard the all-suite yacht Star Breeze. This is the Caribbean for those with a taste for something a bit more exotic. Colonial influences are still going strong here, from the “Little England” island of Barbados to still-very-Dutch Aruba, Bonaire, and Curaçao.

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Jewels of the Windward Islands
Jewels of the Windward Islands

Windstar Cruises8 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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