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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.

10 Best Caribbean Small Cruises for 2021

Caribbean Cruises (31 Results)
Trip NameFromDaysNext DepartureSummary
Bahamas Sailing Adventure$13997Dec 5, 2021Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas …
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Windward Islands$15808Dec 11, 2021Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, …
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Grenadine Islands$13607Jan 2, 2022Departing from Barbados on this 7-day roundtrip Caribbean cruise aboard the Royal Clipper luxury sailing ship, this relaxing trip through the …
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Leeward Islands$15208Nov 27, 2021The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, Dominica, …
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Panama Canal: Barbados to Panama$343015Nov 6, 2021Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to …
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Antigua to Barbados$15808Dec 4, 2021Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing …
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Fort Lauderdale to Bridgetown$470011Dec 17, 2021Discover the Caribbean on this 11-day sailing adventure. Visit the colorful small cities and the exceptional beaches this archipelago is famous for …
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Caribbean: Round-trip Philipsburg$926515Dec 21, 2021Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious …
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Caribbean: Bridgetown - Curacao$525510Dec 4, 2021Join the Sea Cloud ll on this 10-day sailing adventure from Bridgetown to Curacao. Clear your mind in this paradisaical destination that mixes …
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Caribbean: Round-trip Philipsburg$43608Dec 14, 2021Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s …
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Top 10 Luxury Caribbean Cruises for 2021

Caribbean Cruise Destinations

Best Small Caribbean Cruise Ships & Sailboats

Ship NameMax PassengersFromSummary
Liberty Clipper24$1399The Liberty Clipper is a 125-foot beautifully renovated gaff-rigged schooner, a replica of the renowned Baltimore Clippers, made famous over a …
Sea Cloud II94$2715The 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'Urville184$800Experience a luxurious setting where the accent is on authenticity and passion for travel aboard this glamorous limited-capacity yacht with …
Sea Cloud64$2850With 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$3090Sea 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$3390The 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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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.
 

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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.
 

Video: Sailing the Caribbean on a Small Ship Cruise

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