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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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Top 10 Leeward Islands Small Ship Cruises for 2025-2026

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10 Best Leeward Islands Luxury Small Ship Cruises

Trip NameFromDaysNext DepartureSummary
Westbound Atlantic Ocean Crossing$460025Oct 29, 2025Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San …
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Grenadine Islands$17008Jan 18, 2025On 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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Panama to Antigua$383015Nov 15, 2025Starting in Balboa, Panama, sail through warm Caribbean waters as you make your way to the Antigua aboard the Royal Clipper. Over the course of 15 …
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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys$64009Feb 28, 2026From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the …
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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys$68309Jan 30, 2025Discover the Caribbean on a 9-day cruise aboard Le Champlain, featuring white-sand beaches, turquoise waters, and charming islands. Highlights …
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Gliding the Waters of the Windward Islands$82008Jan 18, 2025Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint …
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Sailing the Caribbean$96588Jan 19, 2025Experience 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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Classic Yachtsman Caribbean$20208Nov 29, 2025Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush …
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Discover Eastern Caribbean & Grenadines$1518015Nov 15, 2025Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the …
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Jamaica to Antigua$272012Jan 17, 2026Explore a paradise of vibrant coral reefs, powder-soft sand, and warm island hospitality on this 12-day cruise from Jamaica to Antigua aboard Star …
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