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Bahamas Sailing Trips, Adventures, & Cruises

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Sailing the Bahamas is the quintessential Caribbean escape. Explore tiny cayes, hidden bays, coves, and harbors on some of the over 700 islands in the Bahamas. In Nassau, embark  the Liberty Clipper, which never has a fixed itinerary, letting the Captain chart a course for the best wind, weather & adventures. Travelers will often explore the Exumas, an archipelago of 365 cayes and islands dotting the Caribbean Sea. Eleuthera, one of the Bahamas' Outer Islands, is 110 miles long and just a few miles wide. Explore all the Bahamas on a small ship Caribbean sailing cruise with Adventure Life. Contact one of our Bahamas sailboat cruise specialist for any questions you have about cruising the Caribbean. 

4 Best Bahamas Sailing Trips, Adventures & Small Ship Cruises for 2025-2026

Nassau Lighthouse

Caribbean Escapade

San Juan to Miami
8 Days from $7,590
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites. Enjoy the white sands of Emerald Bay in The Bahamas and visit Nassau's vibrant cityscape and historic sites.
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Big brown pelicans at the Florida Keys

Insider Tip for Sailing Enthusiast

Miami to Miami
10 Days from $9,635
Experience a 10-day luxury cruise exploring Eleuthera, Exumas, and Key West. Dive into vibrant cultures and stunning landscapes aboard Sea Cloud Spirit, offering unparalleled comfort and service.
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Deans Blue Hole

West Caribbean Cruise

Belize - Fort Lauderdale
11 Days from $3,580
Embark on an 11-day SH Vega cruise through the Western Caribbean. Explore Mayan ruins in Belize, relax on Grand Cayman's beaches, snorkel Montego Bay’s reefs, and visit Jamaica’s mountains. Enjoy birdwatching at Great Inagua, swim with sharks in the Exumas, and marvel at Nassau’s beauty.
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Nassau Lighthouse

Island Odyssey: Bahamas to the Grenadines

Nassau - Bridgetown
13 Days from $23,390
Sail on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Begin the trip in Nassau then sail to Compass Cay and explore its pristine beaches, snorkel in crystal-clear waters, or spot marine life from the marina. Explore Long Island on foot or by bike and more!
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3 Best Bahamas Small Cruise Ships & Sailboats for 2025-2026

Ship NameMax PassengersFromSummary
Sea Cloud Spirit136$9635Sea 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 …
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SH Vega152$35805-star elegant Scandi-design boutique ship offers you an intimate setting from which you will be fully immersed in all the sights and scenery of your …
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Emerald Sakara100$7590Emerald Cruises brings our award-winning reputation and service to the world?s oceans and coastlines as we introduce Luxury yacht cruising on our …
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Pink sand beaches in the Bahamas

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Snorkel the warm Caribbean waters on your small ship cruise

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Sunset over the Liberty Clipper

Honeymoon Sailing in the Bahamas

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Catching the wind on our sailing adventure on the Liberty Clipper

Sailing the Bahamas on the Liberty Clipper

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TrustScore 4.8 | 380 reviews
TrustScore 4.8 of 5
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Based on 380 reviews on
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6 hours ago
Very responsive to questions. Helpful with all arrangements
Roz
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1 day ago
The ship company they sent us on was perfect in every detail
lisa wegener
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2 days ago
I’m so glad we found AdventureLife. Jess, our planner, was such a pleasure to work with. She readily shared her extensive knowledge about Panama, she offered good suggestions and creative ideas, kept everything organized and handled the details each step of the way.
Tim King
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3 days ago
Jessica was wonderful! She made every effort to ensure our trip was just what we wanted.
Celine Krafft
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3 days ago
Erin was easy to work with and very helpful. She was patient and helped us figure out the adventure tour we were hoping for in Belize. Can’t wait to go on this trip!
Sam Wedll

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