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Caribbean Small Ship Cruises

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A Caribbean cruise on a small ship or sailboat is the best way to explore the turquoise waters, beaches, rich marine life and cultures of the Caribbean. The vessel you choose for your cruise on has a dramatic impact on the experience. On a small sailboat or small luxury ship with only 24-60 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 SeaDream I or SeaDream IIMandalay, Panorama, or the Liberty Clipper. Up the ante on a luxury small ship like the Variety Voyager, or the Ponant. Escape the average Caribbean cruise by having one of our small ship Caribbean cruise experts design you the perfect trip.

10 Best Caribbean Small Cruises

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6 Best Small Caribbean Cruise Ships & Sailboats

Ship NameMax PassengersFromSummary
Sea Cloud II94$2575The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II …
SeaDream I112$2599The SeaDream I is a chic and stylish yacht designed to accommodate 112 passengers in an intimate and comfortable atmosphere. Cruise along the …
Liberty Clipper24$1299The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a …
Sea Cloud64$3085With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
Mandalay58$1599On 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 II112$1999Join a luxury Caribbean and Mediterranean voyage aboard the boutique ship SeaDream II. This intimate and comfortable ship offers accommodation for …

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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 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.

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