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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$50558Dec 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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Treasure Islands$16008Dec 2, 2023Don'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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British Virgin Islands & French West Indies$87908Jan 27, 2024On this 8-day British Virgin Islands & French West Indies Cruise roundtrip to St. John's aboard Emerald Sakara, relax on the pink sand beaches of …
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Classic Yachtsman Caribbean$16608Dec 2, 2023Royal 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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Leeward Islands$16008Nov 25, 2023The 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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Sailing on the Warm Trade Wind$49558Dec 14, 2023Sail like Christopher Columbus on the balmy trade winds of the Caribbean, drifting from island to island in blissful relaxation aboard Sea Cloud II. …
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Pearls of the Caribbean$42909Nov 5, 2023Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port …
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Windward Islands$16608Dec 9, 2023Board 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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Grenadine Islands$16608Dec 16, 2023On 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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Windward Islands Christmas Cruise$16608Dec 23, 2023Royal 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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All Leeward Islands Luxury Small Ship Cruises

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

Trip NameFromDaysNext DepartureSummary
Pearls of the Caribbean$42909Nov 5, 2023Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port …
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West Indies Island Hopping$88908Dec 2, 2023Experience the beauty of the islands of the Caribbean on this 8-day West Indies Island Hopping cruise roundtrip San Juan aboard the Emerald Sakara. …
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Hidden Charms of the Caribbean$88908Nov 25, 2023Embark on an 8-day Caribbean adventure, sailing from San Juan to St. John's aboard the luxurious Emerald Sakara. Discover the hidden gems of the …
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Hidden Charms of the Caribbean with Chef Ben Robinson$137908Mar 2, 2024Join this 8-day Hidden Charms of the Caribbean adventure with Chef Ben Robinson aboard the Emerald Sakara. Discover the Caribbean's hidden gems, from …
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Pearls of the Caribbean$50909Mar 21, 2024Join 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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All Leeward Islands Small Ship Cruise Deals

1 Best Leeward Island Small Ship Cruise Deals for 2023-2024

Trip NameSaveFromDaysNext DepartureSummary
Southern Caribbean Delights & Panama CanalSavings$1219011Jan 6, 2024Experience the ultimate cruise through the Southern Caribbean, exploring charming islands, historic cities, and the iconic Panama Canal on this …
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