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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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All Leeward Islands Luxury Small Ship Cruises

10 Best Leeward Islands Luxury Small Ship Cruises

Trip NameFromDaysNext DepartureSummary
Treasure Islands$16408Dec 21, 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 …
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Caribbean Yachting Discovery$79908Dec 28, 2024Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry …
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Cruising the Leeward Islands$102708Dec 28, 2024Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning …
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Leeward Islands$16408Dec 28, 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 …
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Vibes of the Virgin Islands$75908Dec 13, 2026Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning …
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Cruising the Leeward Islands$75908Dec 13, 2026Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van …
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Caribbean Yachting Hideaways$71908Dec 21, 2024Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz …
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Caribbean Yachting Discovery with Chef Ben Robinson$69668Jan 25, 2025Embark on an 8-day Caribbean cruise with Chef Ben Robinson aboard the Emerald Azzurra. Enjoy a welcome reception, cooking demo, and special dinners. …
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Caribbean Enchantment$63407Feb 22, 2025Embark on a 7-day Caribbean cruise aboard Emerald Azzurra. Start in Antigua and sail to Les Saintes, Deshaies, Virgin Gorda, and Norman Island. …
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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 …
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