10 Best Caribbean Small Cruises for 2021

Name: Caribbean Tours & Travel
Brand: Adventure Life
Rating: 4.9 (332 reviews)

Trip Name	From	Days	Next Departure	Summary
Bahamas Sailing Adventure	$1399	7	Dec 13, 2020	Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas … 0
Jewels of the Caribbean	$4300	9	Jan 21, 2021	Embark on the Le Champlain on this 9-day cruise to the heart of the West Indies. From Fort-de-France, you will sail the idyllic waters of the … 0
Sailing the Caribbean	$9290	8	Feb 16, 2021	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 … 0
Windward Islands	$2340	8	Dec 12, 2020	Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, … 0
Pearls of the Caribbean	$3420	8	Feb 13, 2021	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, … 0
The Caribbean & Amazon River	$6430	13	Dec 11, 2020	Set sail for an incredibly diverse cruise, taking in Caribbean beaches and incursions into a tropical rainforest. Join a 13-day circuit aboard Le … 0
Grenadines	$2160	8	Jan 2, 2021	Departing from Barbados on this 8-day roundtrip Caribbean cruise aboard the Royal Clipper luxury sailing ship, this relaxing trip through the … 0
Leeward Islands	$2240	8	Dec 12, 2020	The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, Dominica, … 0
St. Lucia & Grenada	$1649	7	Dec 20, 2020	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 … 0
Sail to St. Lucia	$1649	7	Dec 6, 2020	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 … 0

Top 10 Luxury Caribbean Cruises for 2021

Jewels of the Caribbean

Fort de France to Fort de France
9 Days from $4,300

Embark on the Le Champlain on this 9-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.Visit Brimstone Hill Fortress National Park in St. Kitts and Nevis and admire the British Virgin Islands' stunning white-sand beaches

Pearls of the Caribbean

Fort de France to Fort de France
8 Days from $3,420

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! See Saint Lucia and the historic center of Bridgetown and its garrison and tour the Grenadine Islands - one of the world’s most stunning archipelagos

The Caribbean & Amazon River

Cayenne to Fort-de-France
13 Days from $6,430

Set sail for an incredibly diverse cruise, taking in Caribbean beaches and incursions into a tropical rainforest. Join a 13-day circuit aboard Le Dumont-d’Urville, from Cayenne to Fort-de-France, including a 5-day expedition with our naturalist guides.

Fort Lauderdale to Bridgetown

Fort Lauderdale to Bridgetown
11 Days from $3,230

Discover the Caribbean on this 11-day sailing adventure. Visit the colorful small cities and the exceptional beaches this archipelago is famous for as you sit back and relax while sailing one of the most exclusive regions in the world aboard the Silver Whisper.

Pearls of the Caribbean

Fort de France to Fort de France
9 Days from $3,960

Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!

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.

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.

Caribbean: Round-trip Bridgetown via Bequia

Bridgetown to Bridgetown
8 Days from $5,595

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.

San Juan to San Juan

San Juan to San Juan
8 Days from $4,899

Be a part of this magical 8-day adventure aboard the SeaDream ll. Starting and ending in San Juan, Puerto Rico, this cruise visits the most popular spots of the region. Sail through the Caribbean and discover the enchanting and exclusive islands of this perfect archipelago.

A snorkeler walking along a white sandy beach.

Round-trip Charlotte Amalie via St. John

Charlotte Amalie to Charlotte Amalie
8 Days from $3,499

Starting and ending in Charlotte Amalie, St. Thomas, explore undiscovered gems of the Caribbean as you sail this incredible region. Enjoy adventure options and incredible views of the Caribbean's paradisaical islands.

Caribbean Cruise Destinations

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.

Virgin Islands

Take a small ship cruise around the gorgeous U.S. and British Virgin Islands with opportunities to snorkel, relax, soak up the sun, go to National Parks, or meet the locals.

Belize

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

Wander the white-sand beaches of St. Johns on your Virgin Islands cruise

Lesser Antilles

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

Explore the mountainous island of St. Vincent

St. Vincent des Grenadines

Get ready to explore the beautiful island of St. Vincent des Grenadines, and the surrounding islands by cruise to maximize what it has to offer. You can swim or snorkel along the way, and there's plenty to do with Canouan, a gorgeous little island off the coast of St. Vincent des Grenadines with resorts and coral reefs.

Barbados

Take a gorgeous small ship cruise around Barbados where you will have amazing opportunities to swim, snorkel, explore various caves and relax by the beach.

Best Small Caribbean Cruise Ships & Sailboats

Ship Name	Max Passengers	From	Summary
Liberty Clipper	24	$649	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	$2325	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	$800	Experience a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
Sea Cloud	64	$2995	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 …
Sea Cloud Spirit	136	$3345	Sea Cloud Spirit is a modern and elegant windjammer with occupancy for 136 guests and a crew of 85. It gives you an amazing opportunity of traveling …
Variety Voyager	72	$3390	The sleek & modern Variety Voyager is a state of the art mega-yacht which accommodates just 72 passengers in 36 cabins. Enjoy unobstructed views of …

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 laid back 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.

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: In the far south of the Caribbean, 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.