Top 10 Luxury Caribbean Cruises

Set sail for an incredibly diverse expedition cruise, taking in Caribbean beaches and incursions into tropical rainforest aboard Le Dumont-d'Urville. In a setting of white sand, turquoise water and lagoons, you will enjoy some unforgettable bathing.

Pearls of the Caribbean

Fort de France to Fort de France
8 Days from $3,400

Join the Le Champlain on its 8-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!

Between Martinique & Panama

10 Days from $4,460

This 10-day itinerary will give you the opportunity to appreciate the richness of Afro-Caribbean cultures, an azure blue sky, and white-sand beaches. A small paradise in the Venezuelan Caribbean, Los Roques archipelago, has been declared a national park and is an ideal spot to dive and snorkel in a turquoise lagoon with stunning seabeds.

Bustling port of Fort de France, Martinique

Ocean Voyage: Fort-de-France - Ponta Delgada

Fort de France to Ponta Delgada
9 Days from $2,110

Board Le Champlain for an ocean voyage on this 9-day cruise, from sea to sea, or from continent to continent. A few times a year sea lovers, dreamers, and keen observers of endless horizons join this non-stop journey, to enjoy the comfort of the ships for an extended period.

Golf and Pro-Am in the Caribbean

Santo Domingo to Fort de France
11 Days from $7,230

Board Le Champlain for this first “Golf and Pro-Am in the Caribbean” cruise. Set sail to discover a series of carefully chosen courses that will take you from Santo Domingo to Fort-de-France.

Unspoiled beaches and pristine coves in the Caribbean

Caribbean: Santo Domingo - Bridgetown

16 Days from $10,795

Fall in love with the Caribbean on an idyllic 16-day cruise aboard the Sea Cloud. Experience the blue waters of the wonderful Caribbean and breathtaking sceneries along the way.

Tranquil shores on your Virgin Islands cruise

Caribbean: Bridgetown - Colon

Bridgetown to Colon
15 Days from $10,295

Join the Sea Cloud ll on this 15-day sailing adventure from Bridgetown to Colon. Clear your mind in this paradisaical destination that mixes adventure and relaxation perfectly.

San Juan to Charlotte Amalie via St. Kitts

San Juan to Charlotte Amalie
8 Days from $2,999

Join the SeaDream II on this extraordinary and historic 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the relaxed pace of Caribbean life.

Bridgetown Round-trip

Bridgetown to Bridgetown
10 Days from $4,400

Discover the Caribbean on this 10-day sailing adventure. Visit the colorful small towns and exceptional beaches this archipelago is famous for as you sit back and relax aboard the Silver Whisper while sailing in one of the most exclusive regions in the world.

Pearls of the Caribbean

Fort de France to Fort de France
8 Days from $3,790

Join the Le Champlain on its 8-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!

10 Best Caribbean Small Cruises

Caribbean Cruises (113 Results)

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Bahamas Sailing Adventure

7 Days from $1,399

Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas archipelago and the Out Islands, including Eleuthera. Daily shore excursions include snorkeling, kayaking, and paddle boarding in crystal turquoise waters, or optional cultural and wildlife tours.

Caribbean and Orinoco

13 Days from $8,190

Windward Islands

8 Days from $1,500

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.

Pearls of the Caribbean

Fort de France to Fort de France
8 Days from $3,400

Join the Le Champlain on its 8-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!

Grenadines

8 Days from $1,500

Departing from Barbados on this 8-day roundtrip Caribbean cruise aboard the Royal Clipper luxury sailing ship, this relaxing trip through the Grenadines combines snorkeling, hiking, swimming, and boating with relaxing time on the sunny beaches, delicious cafes, and idyllic harbors. Sail to Bequia, Martinique, St. Lucia, and Grenada!

Leeward Islands

8 Days from $1,640

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.

St. Lucia & Grenada

7 Days from $1,649

Learn how to raise the sails of the S/V Mandalay as you sail the turquoise waters of the Caribbean on this 7-day cruise. Rise early and search for marine life, learn local lore of the region, snorkel and swim from the ship, and choose from various island excursions each day on this Caribbean adventure through sun-kissed St. Lucia and Grenada.

Sail to St. Lucia

7 Days from $1,649

Board the S/V Mandalay in St. Lucia for a round-trip 7-day Caribbean cruise. Go where the wind takes you and be prepared to visit a selection of islands like St. Lucia, Martinique, Dominica, Iles Des Saintes, Marie-Galante and possibly some more!

Between Martinique & Panama

10 Days from $4,460

Ocean Voyage: Fort-de-France - Ponta Delgada

Fort de France to Ponta Delgada
9 Days from $2,110

Caribbean Cruise Destinations

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Select from the top-rated small ships that cruise the Caribbean such as the Mandalay, Liberty Clipper, Le Ponant, Panorama and Variety Voyager. Cruise the Bahamas, Cuba, Granada, Trinidad and Tobago and beyond with Adventure Life.

Cuba

Get to know the Cuban people as you stroll the colonial rhythm-filled streets of Havana, Cienfuegos and Trinidad. Enjoy snorkeling and relaxing aboard a small sail boat like the Panorama or Panorama II that accommodate only about 50 passengers, or the luxurious small ships Le Ponant and Variety Voyager.

Bahamas

Set sail for the Bahamas on a small ship sailing cruise. Visit hidden bays, coves, and harbors on some of the hundreds of islands in the Bahamas like the Exumas, an archipelago of 365 cays and islands dotting the Caribbean Sea.

Belize

The tropical paradise of Belize has world class snorkeling, sea kayaking, luxury resorts and jungle lodges. Adventure Life's Belize experts show you the must-see spots.

Lesser Antilles

Take a sailboat or small ship cruise to the Caribbean visiting the islands of Grenada, the Grenadines, St. Lucia, San Maarten. Snorkel, swim and relax on pristine sunny beaches as you meet friendly locals.

7 Best Small Caribbean Cruise Ships & Sailboats

Ship Name	Max Passengers	From	Summary
Liberty Clipper	24	$1399	The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a …
Sea Cloud II	94	$4155	The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II …
Le Dumont-d'Urville	184	$2110	Experience a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
SeaDream I	112	$2399	The SeaDream I is a chic and stylish yacht designed to accommodate 112 passengers in an intimate and comfortable atmosphere. Cruise along the …
Sea Cloud	64	$2795	With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
Mandalay	58	$1599	On the s/v Mandalay, experience a Caribbean few others ever see or even dream of. Partake in raising the sails, take a turn at the helm or just enjoy …
SeaDream II	112	$1999	Join a luxury Caribbean and Mediterranean voyage aboard the boutique ship SeaDream II. This intimate and comfortable ship offers accommodation for …

Caribbean Sailing Cruise Video

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Luxury Caribbean Cruises

What to Expect on a Luxury Caribbean Cruise
When you book a luxury Caribbean cruise aboard one of our hand-selected small ships, you are signing up for an unforgettable combination of comfort and service.

We feature only small ships, yachts, and windjammers for our luxury Caribbean cruises, because we believe that this should be an intimate experience that you share with your loved ones, and that's exactly the ambiance the small ships offer.

While each ship has a unique design, we guarantee elegance and style, in addition to comfortable and spacious suites - often with their own private balconies - and the best onboard amenities of any small Caribbean ships.

Luxury cruises offer all kinds of included activities to fill your days, but there are also add-on packages that can bring even more adventure and exploration to your itinerary. Plus there's plenty of free time built in to these cruises at each port so that you can simply relax on the beach and meander around the small towns if you prefer.

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.

Caribbean Travel Guide

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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.

Highlights of the Caribbean

The Lesser Antilles are home to some of the most popular destinations in the Caribbean, like the Virgin Islands, St. Lucia & St. Martin, where delightful cafes, tranquil towns, and serene beaches highlight the sea side scenery.

The Grenadines:
Sail to Grenada, Bequia, Union Island, Mayreau, Tobago Cays, Carriacou, Sandy Island, Canouan and Happy Island; try some of the famous local Caribbean rum; relax on the beach; or participate in various land excursions.

The Bahamas: As you cruise through the Bahamas on a small sailboat, get into the groove of the laidback lifestyle of the islands, the culinary delights of the local cuisine, and perhaps even have a chance to try hoisting the sails or taking over the helm of your sailboat.

Cuba: What was once a secluded Caribbean nation, politically estranged from much of the Western world, has recently been gaining more and more attention as policies evolve. Stops in Havanna, Santiago, and other towns will enchant you.

The Virgin Islands: Offer you some of the best snorkeling opportunities in the whole Caribbean, featuring crystal clear waters and diverse marine life, in addition to stops in charming port towns along the way, where you can get a taste of the local island culture.

The Panama Canal: See the breathtaking marvel that is the Panama Canal, when the greatest minds and thousands of dedicated workers labored internationally to connect the Atlantic & Pacific trade routes.