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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 2022-2023

Trip NameFromDaysNext DepartureSummary
Caribbean: Round-trip Philipsburg$926515Dec 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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Windward Islands$24208Dec 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$23608Dec 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$23608Nov 26, 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$618014Dec 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$48608Nov 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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Windward Islands Christmas Cruise$24208Dec 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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Grenadine Islands$24208Dec 17, 2022On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of …
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Classic Yachtsman Caribbean$24208Dec 3, 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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Sailing the Caribbean$108808Jan 20, 2023Experience the Caribbean in the most authentic way under the 30 white sails of Sea Cloud on this 8-day round trip cruise of Barbados. As you delight …
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All Leeward Islands Luxury Small Ship Cruises

9 Best Leeward Island Luxury Small Ship Cruises for 2022-2023

Trip NameFromDaysNext DepartureSummary
Caribbean: Round-trip Philipsburg$926515Dec 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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Christmas and New Year in the Caribbean$618014Dec 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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Transatlantic: Las Palmas to St Maarten$1071018Nov 25, 2022Sail across the Atlantic Ocean on this exclusive 18-day, once-in-a-lifetime offshore adventure on the Sea Cloud schooner. Enjoy an authentic sailing …
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Pearls of the Caribbean$36209Mar 13, 2023Le Dumont-d’Urville brings you a 9-day cruise to the heart of the most enchanting islands in the Caribbean Sea, combining long white-sand beaches …
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Pearls of the Caribbean$36209Nov 25, 2022Join 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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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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Transatlantic:Malaga to St.Maarten$394025Nov 2, 2022This 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$544013Jan 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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Transatlantic: Praia - Philipsburg$1012016Nov 29, 2022Sail around the Atlantic ocean as Sea Cloud II sail from the island in the Southwest coast Praia to Philipsburg, St Maarten.enjoying the beautiful …
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