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Lesser Antilles Small Ship Cruises

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Take a small ship cruise to the beautiful archipelago of the Lesser Antilles that make up a volcanic island arc between the Greater Antilles and South America. Visit the islands of Grenada, the Grenadines, the Virgin Islands, St. Lucia, San Maarten, and beyond. Snorkel, swim and sail around numerous Caribbean Islands while relaxing on pristine sunny beaches as you meet friendly locals. Consider traveling on a small ship cruise in order to be able to access smaller, beaches reefs, and coves. Contact Adventure Life's Caribbean cruise experts for help designing the perfect cruise to the Lesser Antilles.
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Top 39 Lesser Antilles Caribbean Small Ship Cruises for 2025-2026

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9 Best Lesser Antilles Luxury Caribbean Small Ship Cruises for 2025-2026

Trip Name From Days Next Departure Summary
Pearls of the Caribbean $5,520 9 Dec 12, 2025 Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!
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Discover Eastern Caribbean & Grenadines $15,180 15 Nov 15, 2025 Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.
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Westbound Atlantic Ocean Crossing $4,820 25 Oct 29, 2025 Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.
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Top 39 Cruise Deals to the Lesser Antilles for 2025-2026

Trip Name From Days Next Departure Summary
Eastern Caribbean with St. Barths $7,590 8 Dec 20, 2026 Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.
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Cruising the Leeward Islands $10,670 8 Mar 22, 2025 Embark on an 8-day Cruising the Leeward Islands aboard Emerald Sakara from Marigot roundtrip. Explore Anguilla, Virgin Gorda, and other stunning destinations, immersing yourself in picturesque landscapes, vibrant cities, and unique natural wonders.
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Caribbean Sojourn $7,190 7 Jan 03, 2027 Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufrière’s mud baths, Falmouth Harbour’s historic dockyard, Îles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
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Save the Best for Last $3,980 8 Mar 27, 2025 Sail aboard the Sea Cloud on a 10-day Caribbean adventure through the British Virgin Islands, St. Barths, Nevis, and St. Maarten. Explore Virgin Gorda’s iconic Baths, unwind at the Bitter End Yacht Club, and sail the Sir Francis Drake Channel to Jost van Dyke. Stroll St. Barths’ luxury shops, discover Nevis’ lush rainforests, and end in vibrant Philipsburg.
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Windward Islands $2,020 8 Dec 13, 2025 Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.
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Classic Yachtsman Caribbean $2,020 8 Nov 29, 2025 Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.
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Grenadine Islands $2,020 8 Dec 06, 2025 On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.
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Western Antilles $2,480 8 Oct 05, 2026 Explore the Caribbean in this 8-day itinerary. Start in Philipsburg, Sint Maarten, Gustavia, Saint-Barthelemy, Deshaies in Guadeloupe, Saint-Pierre, Martinique, Soufriere, St Lucia, and conclude in Bridgetown, Barbados.
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Leeward Islands $1,870 8 Mar 22, 2025 The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.
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Treasure Islands $1,960 8 Nov 22, 2025 Don'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 locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!
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Lesser Antilles Travel Guide

Best Lesser Antilles Small Ship Cruise Lines for 2025-2026
  • Ponant - serves as a global ambassador for the "French Touch." It makes every effort to keep its particular cruising philosophy, with a French crew, discreet service, sophisticated cuisine, and established partners. Your dream of the Lesser Antilles, Caribbean cruise onboard the cozily intimate ship Le Champlain is thus made possible through the combination of an authentically genuine voyage experience together with discreet luxury. 
  • Silversea Cruises - Known for their exquisite onboard service and innovative, enticing itineraries, Silversea cruises let you discover some of the world's most captivating destinations. A Caribbean island cruise transports you to mild breezes and swaying palm trees. Silver Wind enables you to escape to the yachting havens of the Lesser Antilles, which are inaccessible to big ships.
  • Lindblad Expeditions - return to the romantic era of tall ships on a voyage among the idyllic islands of the Caribbean—a place perfectly suited to the aesthetic beauty of sailing aboard an authentic square-rigger. The iconic ship Sea Cloud serves as a home base for exploring the Caribbean's hidden gems and the Lesser Antilles.
  • Star Clippers Americas - a modern cruise line that re-creates the famous clippers that sailed the oceans in the 19th century and offers a chance to cruise onboard the Tall Ship Royal Clipper in the Lesser Antilles in the Caribbean Sea.

 

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