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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.
All Leeward Islands Small Ship Cruises

Top 10 Leeward Island Small Ship Cruises for 2023-2024

Trip NameFromDaysNext DepartureSummary
On the Sunny Side of Life$47558Dec 14, 2023Discover deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the islands' sugar cane …
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Enjoy Caribbean Rhythms at the Turn of the Year$819516Dec 21, 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 …
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Front Row Seat at the Famous Bucket Regatta$749511Mar 17, 2023Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s …
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Windjammer Rendezvous in the Lesser Antilles$678511Mar 27, 2023On this 11-day voyage aboard Sea Cloud, windjammers can enjoy the Caribbean's lush green landscapes, stunning beaches, a relaxed sailor lifestyle, …
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Windward Islands Christmas Cruise$16208Dec 24, 2022Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing …
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Windward Islands$16208Dec 10, 2022Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, …
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Treasure Islands$15608Dec 3, 2022Don'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 …
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Leeward Islands$15608Dec 10, 2022The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, Dominica, …
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Christmas and New Year in the Caribbean$618013Dec 23, 2022Spend an unforgettable festive season celebrating Christmas and New Year's in the Caribbean aboard Le Dumont-d'Urville. Cruise from Fort-de-France to …
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Philipsburg Round Trip$59459Nov 28, 2022Join the Sea Cloud Spirit on a roundtrip Caribbean cruise to St. Maarten which includes stops in Puerto Rico, the British Virgin Islands, and France. …
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All Leeward Islands Luxury Small Ship Cruises

9 Best Leeward Island Luxury Small Ship Cruises for 2023-2024

Trip NameFromDaysNext DepartureSummary
Christmas and New Year in the Caribbean$618013Dec 23, 2022Spend an unforgettable festive season celebrating Christmas and New Year's in the Caribbean aboard Le Dumont-d'Urville. Cruise from Fort-de-France to …
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Relaxed Festive Days Under Palms$1018517Dec 20, 2022Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious …
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Caribbean and Brazilian Coasts$915113Oct 11, 2023Explore the Caribbean and Brazilian coasts on this 13-day voyage aboard SH Vega. Embark on a journey that will take you to a region of the planet …
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San Juan to Bridgetown - Door to Door$490010Jan 30, 2023Discover the Caribbean's most gorgeous and spectacular beaches on this 10-day cruise from San Juan to Bridgetown. From the blue waters of San Juan to …
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In the heart of the West Indies : Bridgetown - Vieux Fort$38409Mar 5, 2023The Dumont-d'Urville offers a 9-day Caribbean trip that takes you to the most beautiful islands in the region. Begin your journey from Bridgetown to …
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Pearls of the Caribbean$38409Jan 16, 2023Join Le Dumont-d'Urville on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea …
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Transatlantic:Malaga to St.Maarten$406025Nov 1, 2023This once-in-a-lifetime sailing expedition starts at the tropical paradise island of St. Maarten and voyages across the Atlantic Ocean all the way to …
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Santo Domingo and Caribbean treasures$576013Jan 4, 2023From Santo Domingo to Fort-de-France, succumb to the charms of the Caribbean aboard a new 13-day cruise. Swimming and spectacular discoveries await …
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Pure Sailing- Crossing the Atlantic$1281517Nov 29, 2022Sail around the Atlantic ocean as Sea Cloud II sail from the island on the Southwest coast of Praia to Gustavia enjoying the beautiful beaches and …
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