10 Best Caribbean Small Ship Cruises for 2023-2024

Name: Caribbean Tours & Travel
Brand: Adventure Life
Rating: 4.9 (465 reviews)

Philipsburg Roundtrip
8 Days from $4,755

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.

Grenadine Islands

Bridgetown to Bridgetown
8 Days from $1,620

On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.

Dock going out into the crystal blue ocean

Classic Yachtsman Caribbean

Antigua to Barbados
8 Days from $1,660

Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing journey is unforgettable, with destinations including Barbados, St. Lucia, Dominica, Antigua, Martinique, and more!

Relax in the sunny squares of historic Savannah

Boston, MA to Nassau, Bahamas

Boston - Nassau
16 Days from $8,089

On this 16-day journey along the United States' Atlantic Coast, board the Ocean Voyager. Sail from Boston, Massachusetts to Nassau, Bahamas. Explore historic ports such as Newport, RI; Baltimore, MD; Wilmington, NC; Charleston, SC; and Savannah, GA aboard the Ocean Voyager.

Sailing the Caribbean

8 Days from $11,300

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 in the comfort of this sailing schooner, there will be opportunities to snorkel the vibrant reefs of these turquoise waters, and relax on the beaches of Dominica, the Grenadines, and St. Lucia.

Play on the famously beautiful beaches of St. Barth's

Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb
15 Days from $8,195

Explore the best of the Caribbean on this cruise aboard the Sea Cloud. From the Dutch Colonial port town of Philipsburg, sail to the British Virgin Islands, Grenada, and St. Vincent and the Grenadines. From there cruise to St. Lucia, Antigua, and Barbuda. Relax in Gustavia on St. Barthelemy, then stop in Anguilla before returning to Philipsburg.

Stroll along the beautiful beaches of the Caribbean

Front Row Seat at the Famous Bucket Regatta

Round-trip Philipsburg
11 Days from $7,925

Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg hang in the air wherever you go.

Windjammer Rendezvous in the Lesser Antilles

Phillipsburg Roundtrip
11 Days from $7,215

On this 11-day voyage aboard Sea Cloud, windjammers can enjoy the Caribbean's lush green landscapes, stunning beaches, a relaxed sailor lifestyle, and a vibrant undersea world along the Lesser Antilles.

Panama to Antigua

15 Days from $4,370

Starting in Balboa, Panama, sail through warm Caribbean waters as you make your way to the Antigua aboard the Royal Clipper. Over the course of 15 days visit Grenada, Bonaire, Curacao, Aruba, and Colombia before arriving in Panama.

Windward Islands

Bridgetown to Bridgetown
8 Days from $1,620

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.

Top 6 Luxury Caribbean Small Ship Cruises for 2023-2024

Trip Name	From	Days	Next Departure	Summary
Pearls of the Caribbean	$4480	9	Feb 5, 2023	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 … 0
Hidden Charms of the Caribbean	$4510	8	Nov 25, 2023	Embark on an 8-day Caribbean adventure, sailing from San Juan to St John's aboard the luxurious Emerald Sakara. Discover the hidden gems of the … 0
San Juan to Bridgetown - Door to Door	$5750	10	Jan 30, 2023	Discover the Caribbean's most gorgeous and spectacular beaches on this 10-day cruise from San Juan to Bridgetown. From the blue waters of San Juan to … 0
In the heart of the West Indies : Bridgetown - Vieux Fort	$4050	9	Mar 5, 2023	The Dumont-d'Urville offers a 9-day Caribbean trip that takes you to the most beautiful islands in the region. Begin your journey from Bridgetown to … 0
Pearls of the Caribbean	$4290	9	Nov 5, 2023	Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port … 0
Dream of A Lifetime: Transatlantic Crossing	$14245	18	Nov 27, 2023	Be a part of a unique 18-day Transatlantic sailing experience aboard the luxurious Sea Cloud. Cruise across the magnificent Atlantic Ocean on your … 0

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.

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.

Take a leisurely stroll through beautiful Bridgetown

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.

8 Best Small Caribbean Cruise Ships & Sailboats for 2023-2024

Ship Name	Max Passengers	From	Summary
Royal Clipper	227	$1620	The Royal Clipper is the largest full-rigged sailing ship in the world, carrying just 227 privileged guests aboard. She offers the ultimate tall ship …
Sea Cloud II	94	$4655	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 …
Liberty Clipper	24	$1499	The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a …
Le Dumont-d'Urville	184	$4050	Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
Sea Cloud	64	$4755	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	$4945	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	$2990	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 …

All Caribbean Videos

Caribbean Sailing Cruise Video

All Caribbean Articles

Caribbean Small Ship Cruising Guide & Travel Tips

Snorkel and dive in the clear waters of the Caribbean

Caribbean Island Overview

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!

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.

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 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.

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.

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.

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.

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.