10 Best Caribbean Small Cruises for 2021

Name: Caribbean Tours & Travel
Brand: Adventure Life
Rating: 4.9 (216 reviews)

Trip Name	From	Days	Next Departure	Summary
Bahamas Sailing Adventure	$1399	7	Dec 5, 2021	Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas … 0
Sailing the Caribbean	$9870	8	Feb 6, 2022	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	$1580	8	Dec 11, 2021	Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, … 0
Grenadine Islands	$1360	7	Jan 2, 2022	Departing from Barbados on this 7-day roundtrip Caribbean cruise aboard the Royal Clipper luxury sailing ship, this relaxing trip through the … 0
Leeward Islands	$1520	8	Nov 27, 2021	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
Panama Canal: Barbados to Panama	$3500	15	Nov 6, 2021	Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to … 0
Antigua to Barbados	$2380	8	Dec 4, 2021	Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing … 0
Fort Lauderdale to Bridgetown	$4700	11	Dec 17, 2021	Discover the Caribbean on this 11-day sailing adventure. Visit the colorful small cities and the exceptional beaches this archipelago is famous for … 0
Caribbean: Round-trip Philipsburg	$9265	15	Dec 21, 2021	Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious … 0
The Essential of the Caribbean	$5760	13	Mar 8, 2022	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 … 0

Top 10 Luxury Caribbean Cruises for 2021

Fort Lauderdale to Bridgetown

Fort Lauderdale to Bridgetown
11 Days from $4,700

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.

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.

Caribbean: Bridgetown - Curacao

Bridgetown to Willemstad
10 Days from $5,200

Join the Sea Cloud ll on this 10-day sailing adventure from Bridgetown to Curacao. Clear your mind in this paradisaical destination that mixes adventure and relaxation perfectly.

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.

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.

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.

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.

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.

Charlotte Amalie to San Juan

Charlotte Amalie to San Juan
8 Days from $3,299

Explore undiscovered gems of the Caribbean as you sail the incredible region on this unique 8-day adventure from Charlotte Amalie to San Juan on the SeaDream II. Along the way, visit a variety of beautiful ports including Water Island, Sandy Ground, Gustavia, Soper's Hole, Prickly Pear, and more.

Bridgetown to Fort Lauderdale

Bridgetown to Fort Lauderdale
10 Days from $3,780

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

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	$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	$2730	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	$3620	Experience a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
Sea Cloud	64	$4290	With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
Sea Cloud Spirit	136	$3085	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 …
Vela	26	$2550	Her name means “sail.” One look, and you’ll be taken back to a time when tall ships ruled the waves. Everything about Vela will light your …
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 …

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Caribbean Sailing Cruise Video

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.

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Caribbean Travel Guide

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.