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Islands of the Caribbean

Caribbean Luxury Tours & Cruises

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The Caribbean islands are an amazing location to relax with your family or friends, with their pristine white-sanded beaches and crystal clear waters. The benefits of embarking on a small ship luxury cruise to the Caribbean include being able to access smaller reefs, coves, and beaches with your smaller vessel. We have a wide range of cruise itineraries, going through the British virgin islands, the lesser Antilles, Netherlands Antilles, and many more archipelagos. Expect to see the crystal clear waters throughout your trip with the white-sanded beaches, to help you relax on your trip of a lifetime. Contact our travel specialists to start planning your luxury Caribbean cruise today!
All Caribbean Tours

3 Best Luxury Cruises & Tours of the Caribbean for 2024-2025

All Caribbean Tours
St George's Harbor - Grenada

Pearls of the Caribbean

Fort de France to Fort de France
9 Days from $5,430
Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, Bequia Island and tour the Grenadine Islands - one of the world’s most stunning archipelagos
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Explore the beautiful Canary Islands

Transatlantic:Malaga to St.Maarten

Malaga to Philipsburg
25 Days from $4,180
This 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 Spain. Experience the Caribbean, the vast Atlantic Ocean, and the Old World of Spain aboard the sailing schooner Star Flyer.
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The sun sets off the Canary Islands

Dream of A Lifetime: Transatlantic Crossing

18 Days from $15,725
Be a part of a unique 18-day Transatlantic sailing experience aboard the luxurious Sea Cloud. Cruise across the magnificent Atlantic Ocean on your way from Las Palmas, Gran Canaria to the idyllic beaches of the Caribbean, where your tour ends in tranquil Bridgetown, Barbados.
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Caribbean Small Cruise Ships & Sailboats

Top 6 Ships Cruising the Caribbean for 2024-2025

Caribbean Small Cruise Ships & Sailboats
Le Champlain

Le Champlain

Experience a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with environmentally-friendly equipment. Le Champlain features elegantly designed cabins, spacious suites with windows, and lounge areas opening on to the outside, offering a unique cruising experience.
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Le Dumont-d'Urville Ship

Le Dumont-d'Urville

Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with environmentally-friendly equipment. Le Dumont-d'Urville features elegantly designed cabins, spacious suites with windows, and lounge areas opening to the outside, offering a unique cruising experience.
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Silver Whisper

Enjoy Silver Whisper's relaxing, sophisticated, and genuinely elegant atmosphere. This multi-million dollar refit makes her one of the most technically up to the minute ships at sea. Admire the stunning beauty of Europe & the Caribbean aboard this 382 passenger ship.
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Sea Cloud

With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. Multiple decks allow you to enjoy the ambiance of the Mediterranean & Caribbean Seas in tranquility as the wind guides the journey.
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All Caribbean Articles

Caribbean Travel Guide

Snorkel and dive in the clear waters of the Caribbean

Caribbean Island Guide

The Caribbean is so much more than sun, sand & surf. Various islands allow travelers to sample regional flavor & local adventures. The close proximity to the U.S. makes the Caribbean a perfect destination for a getaway. Get acquainted with some highlights of specific islands to plan a trip that is perfectly suited for you!
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A dolphin jumps out of the water

Wildside of the Virgin Islands

A trip to the Caribbean has so much more to offer travelers than beaches and sunbathing. It might come as a surprise that this destination could excite wildlife enthusiasts! The Caribbean islands have an unexpected variety of wildlife to observe. Besides marine life, there are exotic plants, frogs, iguana lizards, bats, and an array of bird species.
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Wander white sand beaches on your Caribbean cruise

WindJammer Cruises in the Caribbean

Experience the Caribbean in the most authentic way possible, under the majestically masted sails of a true windjammer. In addition to the megayacht tours of the Caribbean we offer, Adventure Life has hand-selected the best luxurious clippers in the Caribbean that offer classic windjammer cruises.
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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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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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Snorkel and dive in the clear waters of the Caribbean

Caribbean Island Guide

The Caribbean is so much more than sun, sand & surf. Various islands allow travelers to sample regional flavor & local adventures. The close proximity to the U.S. makes the Caribbean a perfect destination for a getaway. Get acquainted with some highlights of specific islands to plan a trip that is perfectly suited for you!
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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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Enjoy remote ports of call on your Diamant sailing cruise

Our Favorite Caribbean Cruise Ports for Small Ships

Cherish the sun-kissed sand and idyllic beachscapes of the Caribbean from the intimate atmosphere of a small ship cruise as you visit our favorite Caribbean cruise ports.
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All Caribbean Videos

Caribbean Videos

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Inspiring Caribbean Stories

Catching the wind on our sailing adventure on the Liberty Clipper

Sailing the Bahamas on the Liberty Clipper

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Arabella Aft

Spanish Virgin Islands Cruise on the Arabella

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TrustScore 4.9 | 209 reviews
TrustScore 4.9 of 5
total score
Based on 209 reviews on
review score
7 hours ago
I have travelled with Adventure Life previously and certainly eager to do it again. Kassandra made excellent and honest suggestions while taking the time to understand what was important to us.
Susan
review score
1 day ago
They answered every question and concern that I had and put me at ease. Very excited for this once in a life-time trip.
Customer Tim
review score
2 days ago
I am a returning client to Adventure Life and am very pleased with their commitment to put together a great trip. Clara replied and clarified to any and all questions we had.
Claire Palmer
review score
4 days ago
Jessica was very responsive to my questions and never balked when I asked her to go back and find more options. She really worked hard to find the right cruise for us.
Amy Siegel
review score
4 days ago
Friendly, accommodating, knowledgeable, timely. They have made us feel very comfortable for our trip!
Gregg Chamberlain

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