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Wander the white-sand beaches of St. Johns on your Virgin Islands cruise

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 2023-2024

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Mountains by the ocean in St Lucia
On the Sunny Side of Life
Philipsburg Roundtrip
8 Days from $4,755
Discover deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the islands' sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg hang in the air wherever you go.
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White Sand Beach in Barbados
Grenadine Islands
Bridgetown to Bridgetown
8 Days from $1,620
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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Dock going out into the crystal blue ocean
Classic Yachtsman Caribbean
Antigua to Barbados
8 Days from $1,660
Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing journey is unforgettable, with destinations including Barbados, St. Lucia, Dominica, Antigua, Martinique, and more!
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Pelicans hanging out in the ocean
Sailing the Caribbean
8 Days from $11,590
Experience the Caribbean in the most authentic way under the 30 white sails of Sea Cloud on this 8-day round trip cruise of Barbados. As you delight in the comfort of this sailing schooner, there will be opportunities to snorkel the vibrant reefs of these turquoise waters, and relax on the beaches of Dominica, the Grenadines, and St. Lucia.
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Play on the famously beautiful beaches of St. Barth's
Enjoy Caribbean Rhythms at the Turn of the Year
Caribbean: Round-trip Philipsb
15 Days from $10,495
Explore the best of the Caribbean on this cruise aboard the Sea Cloud. From the Dutch Colonial port town of Philipsburg, sail to the British Virgin Islands, Grenada, and St. Vincent and the Grenadines. From there cruise to St. Lucia, Antigua, and Barbuda. Relax in Gustavia on St. Barthelemy, then stop in Anguilla before returning to Philipsburg.
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Stroll along the beautiful beaches of the Caribbean
Windjammer Rendezvous in the Lesser Antilles
Phillipsburg Roundtrip
11 Days from $7,215
On this 11-day voyage aboard Sea Cloud, windjammers can enjoy the Caribbean's lush green landscapes, stunning beaches, a relaxed sailor lifestyle, and a vibrant undersea world along the Lesser Antilles.
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Gatun Lock of the Panama Canal
Panama to Antigua
15 Days from $4,370
Starting in Balboa, Panama, sail through warm Caribbean waters as you make your way to the Antigua aboard the Royal Clipper. Over the course of 15 days visit Grenada, Bonaire, Curacao, Aruba, and Colombia before arriving in Panama.
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Pink beach huts in the Caribbean
Windward Islands
Bridgetown to Bridgetown
8 Days from $1,660
Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, Dominica, Antigua, St. Kitts, Martinique, and more! Snorkel in turquoise reefs, explore tropical rainforests, relax on the sun-kissed beaches, and delight in exotic markets and charming seaside cafes.
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Tropical Caribbean Beach in Martinique
Windward Islands Christmas Cruise
Bridgetown to Bridgetown
8 Days from $1,660
Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing journey is unforgettable, with destinations including Barbados, St. Lucia, Dominica, Antigua, St. Kitts, Martinique, and more!
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Tropical waterfall and turquoise pool in lush forest
Treasure Islands
Philipsburg to Philipsburg
8 Days from $2,400
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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All Lesser Antilles Luxury Small Ship Cruises

4 Best Lesser Antilles Luxury Caribbean Small Ship Cruises for 2023-2024

Trip NameFromDaysNext DepartureSummary
Hidden Charms of the Caribbean$45108Nov 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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Rainforests and Riches of the Caribbean & Brazil$712813Oct 10, 2023Explore the Caribbean and Brazilian coasts on this 13-day voyage aboard SH Vega. Embark on a journey that will take you to a region of the planet …
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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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Dream of A Lifetime: Transatlantic Crossing$1424518Nov 27, 2023Be 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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Top 6 Cruise Deals to the Lesser Antilles for 2023-2024

Trip NameSaveFromDaysNext DepartureSummary
Leeward IslandsSavings$24008Nov 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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Treasure IslandsSavings$24008Dec 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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Windward IslandsSavings$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 IslandsSavings$16208Mar 25, 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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Transatlantic: Las Palmas to BarbadosSavings$241016Nov 3, 2023Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic …
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Ocean CrossingSavings$406025Oct 25, 2023Ideal for people who love being on the open sea, this spectacular tall ship cruise takes you from the city of Malaga, Spain all the way to the Canary …
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Lesser Antilles Travel Guide

Peaceful seclusion in the Caribbean
Best Time to Visit the Lesser Antilles?
Get information about the dry versus wet season weather averages in Trinidad, Tobago, and Barbados.
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Pelicans hanging out in the ocean
Caribbean Cruise: When to Go?
Discover the best time of year to sail the Caribbean on a small ship or sailboat. Find the best month for your Caribbean cruise, whether you want an active vacation spent kayaking, snorkeling and fishing, or a restful time just lounging by the clear turquoise water.
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Blowing where the wind takes us on the Liberty Clipper
Caribbean Cruises
Small ships provide a fun and unique way to explore the islands of the Caribbean. Water activities can be conveniently planned from the vessel, and time spent on board always provides beautiful scenery as well as good company.
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Best Lesser Antilles Small Ship Cruise Lines for 2023-2024
  • 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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