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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 2022-2023

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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 $1,620
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 $10,880
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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Stroll along the white sandy beaches of St. Barth's
Relaxed Festive Days Under Palms
Round-trip Philipsburg
17 Days from $10,185
Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious Sea Cloud on this fantastic 15-day small ship cruise.
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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
16 Days from $8,195
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
Front Row Seat at the Famous Bucket Regatta
Round-trip Philipsburg
11 Days from $7,495
Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg hang in the air wherever you go.
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Stroll along the beautiful beaches of the Caribbean
Windjammer Rendezvous in the Lesser Antilles
Phillipsburg Roundtrip
11 Days from $6,785
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 $3,500
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 $1,620
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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All Lesser Antilles Luxury Small Ship Cruises

10 Best Lesser Antilles Luxury Caribbean Small Ship Cruises for 2022-2023

Trip NameFromDaysNext DepartureSummary
Relaxed Festive Days Under Palms$1018517Dec 20, 2022Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious …
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Christmas and New Year in the Caribbean$618013Dec 23, 2022Spend an unforgettable festive season celebrating Christmas and New Year's in the Caribbean aboard Le Dumont-d'Urville. Cruise from Fort-de-France to …
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Pearls of the Caribbean$38409Nov 25, 2022Join Le Dumont-d'Urville on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea …
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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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Pure Sailing- Crossing the Atlantic$1406518Nov 25, 2022Sail across the Atlantic Ocean on this exclusive 18-day, once-in-a-lifetime offshore adventure on the Sea Cloud schooner. Enjoy an authentic sailing …
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San Juan to Bridgetown$490010Jan 30, 2023Discover the Caribbean's most gorgeous and spectacular beaches on this 10-day cruise from San Juan to Bridgetown. From the blue waters of San Juan to …
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In the heart of the West Indies : Bridgetown - Vieux Fort$38409Mar 5, 2023The Dumont-d'Urville offers a 9-day Caribbean trip that takes you to the most beautiful islands in the region. Begin your journey from Bridgetown to …
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Transatlantic:Malaga to St.Maarten$394025Nov 2, 2022This once-in-a-lifetime sailing expedition starts at the tropical paradise island of St. Maarten and voyages across the Atlantic Ocean all the way to …
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Santo Domingo and Caribbean treasures$576013Jan 4, 2023From Santo Domingo to Fort-de-France, succumb to the charms of the Caribbean aboard a new 13-day cruise. Swimming and spectacular discoveries await …
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Pure Sailing- Crossing the Atlantic$1218017Nov 29, 2022Sail around the Atlantic ocean as Sea Cloud II sail from the island on the Southwest coast of Praia to Gustavia enjoying the beautiful beaches and …
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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 2022-2023
  • 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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