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Caribbean Small Ship Cruises

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A Caribbean cruise on a small ship or sailboat (Windjammer) is the best way to explore the turquoise waters, beaches, rich marine life and cultures of the Caribbean. The vessel you choose for your Caribbean cruise has a dramatic impact on the experience. On a small sailboat or small luxury ship with only 24-250 passengers aboard, you can access small coves, reefs and ports that are impossible on a huge cruise ship carrying hundreds or even thousands of passengers. Enjoy the serenity of sailing on a small sailboat like the Mandalay, Panorama, or the Liberty Clipper. Up the ante on a luxury small ship like the Variety Voyager, or new Le Champlain and Le Dumont-d'Urville by Ponant. Escape the average Caribbean cruise by having one of our small ship Caribbean cruise experts help design you the perfect trip.
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10 Best Caribbean Small Ship Cruises for 2022-2023

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Top 10 Luxury Caribbean Small Ship Cruises for 2022-2023

Trip NameFromDaysNext DepartureSummary
Relaxed Festive Days Under Palms$1018517Dec 20, 2022Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious …
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Christmas and New Year in the Caribbean$618013Dec 23, 2022Spend an unforgettable festive season celebrating Christmas and New Year's in the Caribbean aboard Le Dumont-d'Urville. Cruise from Fort-de-France to …
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Pearls of the Caribbean$38409Nov 25, 2022Join Le Dumont-d'Urville on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea …
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Dream of A Lifetime: Transatlantic Crossing$1424518Nov 27, 2023Be a part of a unique 18-day Transatlantic sailing experience aboard the luxurious Sea Cloud. Cruise across the magnificent Atlantic Ocean on your …
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Pure Sailing- Crossing the Atlantic$1394018Nov 25, 2022Sail across the Atlantic Ocean on this exclusive 18-day, once-in-a-lifetime offshore adventure on the Sea Cloud schooner. Enjoy an authentic sailing …
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San Juan to Bridgetown$490010Jan 30, 2023Discover 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 …
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In the heart of the West Indies : Bridgetown - Vieux Fort$38409Mar 5, 2023The 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 …
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Transatlantic:Malaga to St.Maarten$394025Nov 2, 2022This 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 …
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Santo Domingo and Caribbean treasures$576013Jan 4, 2023From Santo Domingo to Fort-de-France, succumb to the charms of the Caribbean aboard a new 13-day cruise. Swimming and spectacular discoveries await …
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Pure Sailing- Crossing the Atlantic$1207017Nov 29, 2022Sail around the Atlantic ocean as Sea Cloud II sail from the island on the Southwest coast of Praia to Gustavia enjoying the beautiful beaches and …
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8 Best Small Caribbean Cruise Ships & Sailboats for 2022-2023

Ship NameMax PassengersFromSummary
Royal Clipper227$1620The 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 II94$4495The 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 Clipper24$1499The 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'Urville184$3620Discover a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
Sea Cloud64$4755With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
Sea Cloud Spirit136$5635Sea 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 Voyager72$2990The 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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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.
 
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.
 

Video: Sailing the Caribbean on a Small Ship Cruise

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