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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 10 Lesser Antilles Caribbean Small Ship Cruises for 2025-2026

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

Trip NameFromDaysNext DepartureSummary
Pearls of the Caribbean$66209Dec 29, 2024Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, Bequia Island …
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Caribbean Yachting Discovery$104908Dec 28, 2024Experience a luxurious 8-day Caribbean yacht cruise from St. John’s to San Juan aboard an Emerald Cruises luxury yacht. Discover stunning beaches, …
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Pearls of the Caribbean$52009Dec 12, 2025Join 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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Eastern Caribbean with St. Barths$102708Dec 21, 2024Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic …
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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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Caribbean Yachting Hideaways$71908Dec 7, 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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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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Dream of A Lifetime: Transatlantic Crossing$1572518Nov 26, 2024Be a part of a unique 18-day Transatlantic sailing experience aboard the luxurious Sea Cloud. Cruise across the magnificent Atlantic Ocean on your …
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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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