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Leeward Islands Small Ship Cruises

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Experience all the Caribbean has to offer as you enjoy a relaxing small ship cruise of the Leeward Islands. Each stop promises an exciting exploration of these sun-drenched islands, with activities like snorkeling in vibrant coral reefs, learning to sail by the power of the wind, getting to know local cultures and their ways of life, diving among tropical fish and even dolphins, or simply relaxing on the golden beaches. Each day brings a host of new activities as you enjoy the tranquil days in the Antilles, in ports on St. Maarten, Nevis, Antigua, Guadeloupe, St. Barth, Anguilla, St. Thomas, St. Kitts, and many others. Contact our Caribbean travel experts to start planning your cruise of the Leeward Islands.
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10 Best Leeward Islands Luxury Small Ship Cruises

Trip NameFromDaysNext DepartureSummary
Treasure Islands$16408Dec 7, 2024Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous …
Cruising the Leeward Islands$102708Nov 30, 2024Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning …
Leeward Islands$16408Nov 30, 2024The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des …
Classic Yachtsman Caribbean$17008Nov 30, 2024Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing …
A Colorful Caribbean Time-Out$75008Jan 10, 2025Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and …
The Essential of the Caribbean$815013Dec 17, 2024Sail the lovely seas of the Caribbean roundtrip from Fort-de-France to discover the stunning islands of Antigua, Jost van Dyke, Gustavia, and …
Windward Islands$17008Dec 14, 2024Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, …
Grenadine Islands$17008Dec 7, 2024On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of …
Enjoy Caribbean Rhythms at the Turn of the Year$1159515Dec 20, 2024Explore the best of the Caribbean on this cruise aboard the Sea Cloud. From the Dutch Colonial port town of Philipsburg, sail to the British Virgin …
Pearls of the Caribbean$54309Nov 4, 2024Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, Bequia Island …
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