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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 2024-2025

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Mountains by the ocean in St Lucia

On the Sunny Side of Life

Philipsburg Roundtrip
8 Days from $5,055
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 $1,660
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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Boats Moored to the Quay at Bridgetown Harbour

Barbados to Panama

Bridgetown to Balboa
15 Days from $4,440
Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.
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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 $11,095
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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Learn about the history of the Caribbean

Embracing Inner Spirit and Thriving Caribbean Cruise

Saint Martin to Barbados
8 Days from $6,614
Explore the Caribbean in this 8-day itinerary. Start in Philipsburg, Sint Maarten, Gustavia, Saint-Barthélemy, Deshaies in Guadeloupe, Saint-Pierre, Martinique, Soufriere, St Lucia, and conclude in Bridgetown, Barbados.
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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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Beautiful beach in Dominica

Leeward Islands

Philipsburg to Philipsburg
8 Days from $1,600
The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, 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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Tropical waterfall and turquoise pool in lush forest

Treasure Islands

Philipsburg to Philipsburg
8 Days from $1,600
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

6 Best Lesser Antilles Luxury Caribbean Small Ship Cruises for 2024-2025

Trip NameFromDaysNext DepartureSummary
Pearls of the Caribbean$50209Jan 20, 2024Join 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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Pearls of the Caribbean$58309Mar 21, 2024Join 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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West Indies Island Hopping$88908Dec 2, 2023Experience the beauty of the islands of the Caribbean on this 8-day West Indies Island Hopping cruise roundtrip San Juan aboard the Emerald Sakara. …
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Hidden Charms of the Caribbean$88908Dec 9, 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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Hidden Charms of the Caribbean with Chef Ben Robinson$137908Mar 2, 2024Join this 8-day Hidden Charms of the Caribbean adventure with Chef Ben Robinson aboard the Emerald Sakara. Discover the Caribbean's hidden gems, from …
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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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Top 10 Cruise Deals to the Lesser Antilles for 2024-2025

Trip NameSaveFromDaysNext DepartureSummary
Enjoy Caribbean Rhythms at the Turn of the YearSavings$1109515Dec 21, 2023Explore 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 …
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Southern Caribbean Delights & Panama CanalSavings$1219011Jan 6, 2024Experience the ultimate cruise through the Southern Caribbean, exploring charming islands, historic cities, and the iconic Panama Canal on this …
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Hidden Charms of the Caribbean with Chef Ben RobinsonSavings$137908Mar 2, 2024Join this 8-day Hidden Charms of the Caribbean adventure with Chef Ben Robinson aboard the Emerald Sakara. Discover the Caribbean's hidden gems, from …
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Sailing on the Warm Trade WindSavings$49558Dec 14, 2023Sail like Christopher Columbus on the balmy trade winds of the Caribbean, drifting from island to island in blissful relaxation aboard Sea Cloud II. …
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British Virgin Islands & French West IndiesSavings$87908Jan 27, 2024On this 8-day British Virgin Islands & French West Indies Cruise roundtrip to St. John's aboard Emerald Sakara, relax on the pink sand beaches of …
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Christmas Caribbean StyleSavings$1029515Dec 21, 2023Take a 15-day Caribbean cruise on the Sea Cloud II. Martinique's Fort-de-France has tropical jungles and beautiful bays. Visit Grenada's waterfalls, …
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Hidden Charms of the CaribbeanSavings$88908Dec 9, 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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Enchanted BrazilSavings$949920Apr 13, 2024Embark on a 20-day captivating cruise through Brazil and the Caribbean. Experience the vibrant culture of Rio de Janeiro, explore historic Belem, …
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Crossing the EquatorSavings$59999Apr 24, 2024Discover the rich cultural center of Belém, brave the Equator Crossing ceremony aboard World Voyager, explore haunted Devil's Island, unwind in …
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Eastern Caribbean with St. BarthsSavings$88908Dec 2, 2023On an 8-day voyage on the Emerald Azzurra, visit St. Barths and the Eastern Caribbean. Discover the azure waters of Tobago Cay National Park while …
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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 2024-2025
  • 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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