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

Trip Name From Days Next Departure Summary
Eastern Caribbean with St. Barths $7,990 8 Dec 06, 2025 Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbour’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise
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Eastern Caribbean with St. Barths $7,990 8 Nov 22, 2025 Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
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Caribbean Yachting Discovery $8,390 8 Mar 07, 2026 Embark on an 8-day Caribbean cruise aboard Emerald Azzurra from Antigua to St. Thomas. Explore vibrant ports like Barbuda, Illes des Saintes, and Virgin Gorda. Discover unique sites such as Norman Island’s caves and the markets of Guadeloupe. Travel aboard a luxury yacht, exploring beaches, history, and local culture at each stop.
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Vibes of the Virgin Islands $7,590 8 Dec 13, 2026 Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty. Philipsburg’s lively port, Gustavia’s charming streets, and tranquil Saint John Island round out this cruise.
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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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Caribbean Yachting Hideaways $8,390 8 Dec 20, 2025 Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.
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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 7 Cruise Deals to the Lesser Antilles for 2025-2026

Trip Name From Days Next Departure Summary
Exploring South America $21,580 21 Oct 11, 2025 On this 21-day Exploring South America Cruise from Barbados to Brazil aboard SH Vega, explore South America's Atlantic coast from Barbados to Brazil, encountering the Amazon Rainforest's biodiversity, colonial history in cities like Georgetown and Paramaribo, and natural wonders like Lençóis Maranhenses and the Amazon River mouth.
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Grenadines & Windwards Yachting $7,990 8 Nov 15, 2025 Set sail on an 8-day extraordinary Caribbean cruise, discovering pristine beaches and vibrant coral reefs while hopping between culturally rich islands aboard Emerald Sakara. Enjoy pristine beaches, vibrant local cultures, and water activities like swimming and snorkeling.
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Quintessential Caribbean $7,990 8 Jan 09, 2027 Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbour, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays. Enjoy unique experiences and stunning landscapes throughout your cruise.
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Cruising the Leeward Islands $9,990 8 Dec 13, 2026 Set 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 Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
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Caribbean Sojourn $11,990 7 Jan 03, 2027 Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
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Eastern Caribbean with St. Barths $9,990 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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Discover Eastern Caribbean & Grenadines $15,980 15 Jan 16, 2027 Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.
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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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