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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 Lesser Antilles Caribbean Small Ship Cruises for 2021

All Lesser Antilles Cruises
Stroll along the white sandy beaches of St. Barth's
Caribbean: Round-trip Philipsburg
Philipsburg to Philipsburg
15 Days from $9,265
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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Stroll along the beautiful beaches of the Caribbean
The Essential of the Caribbean
Fort-de-France Roundtrip
13 Days from $5,760
Join this 13-day cruise to the heart of the West Indies. From Fort-de-France, you will sail the idyllic waters of the Caribbean Sea to discover stunning islands, as well as historical and architectural landmarks.
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Beautiful beach in Dominica
Leeward Islands
Philipsburg to Philipsburg
8 Days from $1,520
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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Caribbean beach bar
Caribbean: Round-trip Bridgetown via Bequia
Bridgetown to Bridgetown
8 Days from $5,395
Discover the Caribbean on this 8-day sailing adventure. Delight yourself with the perfect Barbados weather, visit Man-o-War Bay, St. George, Chatham Bay, Port Elizabeth and more on this once-in-a-lifetime cruise aboard the Sea Cloud.
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Colorful harbor of Bonaire
Caribbean: Bridgetown - Curacao
Bridgetown to Willemstad
10 Days from $5,120
Join the Sea Cloud ll on this 10-day sailing adventure from Bridgetown to Curaçao. Clear your mind in this paradisaical destination that perfectly mixes adventure and relaxation.
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Mountains by the ocean in St Lucia
Caribbean: Round-trip Philipsburg
Philipsburg to Philipsburg
8 Days from $4,225
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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Mountains by the ocean in St Lucia
Pearls of the Caribbean
Roundtrip Fort-de-France
9 Days from $3,620
Join Le Dumont-d'Urville on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!
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Explore beautiful Jost van Dyke
Charlotte Amalie, St. Thomas to Marigot
Charlotte Amalie to Marigot
8 Days from $3,399
What better way to see the brilliant turquoise waters of the Caribbean than on this exclusive 8-day small ship cruise aboard SeaDream II. This cruise takes in 7 diverse islands of the Caribbean on a voyage from Charlotte Amalie, St. Thomas to Marigot.
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Gustavia Harbor in St. Barths
Charlotte Amalie, St. Thomas Roundtrip
via Long Bay
8 Days from $3,399
The natural beauty of the Caribbean, with miles of beaches, private coves, and brilliant turquoise water is brought to life on this 8-day roundtrip cruise from Charlotte Amalie, St. Thomas. The cruise takes in 7 diverse islands of the Caribbean including Long bay, Saba, Gustavia, Virgin Gorda, Norman Islands, and Jost Van Dyke.
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Enjoy the beautiful blue Caribbean
Charlotte Amalie to San Juan
Charlotte Amalie to San Juan
8 Days from $3,399
The SeaDream II hosts this 8-day Caribbean cruise from Charlotte Amalie to San Juan. Along the way, visit a variety of beautiful port towns, including St. John, Beef Islands, Gustavia, Virgin Gorda, and Jost Van Dyke. Enjoy pristine beaches, experience the most beautiful sunsets, and be greeted by the warm, welcoming people of the Caribbean.
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All Lesser Antilles Luxury Small Ship Cruises

Best Lesser Antilles Luxury Caribbean Small Ship Cruises

All Lesser Antilles Luxury Small Ship Cruises
Stroll along the white sandy beaches of St. Barth's
Caribbean: Round-trip Philipsburg
Philipsburg to Philipsburg
15 Days from $9,265
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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Caribbean beach bar
Caribbean: Round-trip Bridgetown via Bequia
Bridgetown to Bridgetown
8 Days from $5,395
Discover the Caribbean on this 8-day sailing adventure. Delight yourself with the perfect Barbados weather, visit Man-o-War Bay, St. George, Chatham Bay, Port Elizabeth and more on this once-in-a-lifetime cruise aboard the Sea Cloud.
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Colorful harbor of Bonaire
Caribbean: Bridgetown - Curacao
Bridgetown to Willemstad
10 Days from $5,120
Join the Sea Cloud ll on this 10-day sailing adventure from Bridgetown to Curaçao. Clear your mind in this paradisaical destination that perfectly mixes adventure and relaxation.
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Mountains by the ocean in St Lucia
Pearls of the Caribbean
Roundtrip Fort-de-France
9 Days from $3,620
Join Le Dumont-d'Urville on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!
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Explore beautiful Jost van Dyke
Charlotte Amalie, St. Thomas to Marigot
Charlotte Amalie to Marigot
8 Days from $3,399
What better way to see the brilliant turquoise waters of the Caribbean than on this exclusive 8-day small ship cruise aboard SeaDream II. This cruise takes in 7 diverse islands of the Caribbean on a voyage from Charlotte Amalie, St. Thomas to Marigot.
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Gustavia Harbor in St. Barths
Charlotte Amalie, St. Thomas Roundtrip
via Long Bay
8 Days from $3,399
The natural beauty of the Caribbean, with miles of beaches, private coves, and brilliant turquoise water is brought to life on this 8-day roundtrip cruise from Charlotte Amalie, St. Thomas. The cruise takes in 7 diverse islands of the Caribbean including Long bay, Saba, Gustavia, Virgin Gorda, Norman Islands, and Jost Van Dyke.
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Enjoy the beautiful blue Caribbean
Charlotte Amalie to San Juan
Charlotte Amalie to San Juan
8 Days from $3,399
The SeaDream II hosts this 8-day Caribbean cruise from Charlotte Amalie to San Juan. Along the way, visit a variety of beautiful port towns, including St. John, Beef Islands, Gustavia, Virgin Gorda, and Jost Van Dyke. Enjoy pristine beaches, experience the most beautiful sunsets, and be greeted by the warm, welcoming people of the Caribbean.
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Soak in the sun in colorful Marigot
Marigot to San Juan
via Charlestown, Nevis
7 Days from $2,999
Fall in love with the Caribbean on this exclusive 7-day cruise from Marigot to San Juan. Capture the French ambiance of St. Barths by day and night, discover a world of grottos amidst giant boulders on the island of Virgin Gorda, or explore the uninhabited paradise of Norman Island. Celebrate the yachting lifestyle aboard SeaDream II.
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Take a leisurely stroll through beautiful Bridgetown
Bridgetown to Bridgetown
Bridgetown to Bridgetown
8 Days from $3,299
Join this unforgettable 8-day sailing adventure aboard the SeaDream I. Visit incredible landscapes and relax in glamorous hot spots. Delight yourself in European influence and the ideal weather of this region as you cruise round-trip out of Bridgetown, Barbados.
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Take the time to explore St. Lucia
Bridgetown Roundtrip
Bridgetown to Bridgetown
8 Days from $3,399
Discover beautiful and magnificent beaches in the Caribbean on this 8-day Bridgetown Roundtrip small ship cruise. Whether it's the picturesque Le Marin, the stunning Rodney bay, the awe-inspiring Tobago Cays, or the islands of St. Vincent and Grenadines, be able to enjoy every stop along your luxury yachting experience aboard SeaDream I.
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All Lesser Antilles Deals

Top Cruise Deals to the Lesser Antilles for 2021

Trip NameSaveFromDaysNext DepartureSummary
Leeward IslandsSavings$15208Nov 27, 2021The 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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Transatlantic: Lisbon to BarbadosSavings$269017Oct 20, 2022Join the Royal Clipper on a fantastic adventure across the Atlantic Ocean from the capital city of Lisbon, Portugal to Barbados, a heaven on Earth. …
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Fort Lauderdale to BridgetownSavings$470011Dec 17, 2021Discover the Caribbean on this 11-day sailing adventure. Visit the colorful small cities and the exceptional beaches this archipelago is famous for …
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Treasure IslandsSavings$15208Dec 4, 2021Soak in the sun in one of the most magical destinations on the planet, the Caribbean. Don’t miss a chance to lay out on one of the beaches and feel …
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Panama Canal: Barbados to PanamaSavings$350015Nov 6, 2021Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to …
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Grenadine IslandsSavings$13607Jan 2, 2022Departing from Barbados on this 7-day roundtrip Caribbean cruise aboard the Royal Clipper luxury sailing ship, this relaxing trip through the …
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All Lesser Antilles Articles

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. The Caribbean can provide an active vacation of sea kayaking, snorkeling and fishing, or a restful time spent lounging by the clear turquoise water. Whatever your desire, we can help you determine the optimum months for your trip.
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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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