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.

5 Best Bahamas Sailing Trips, Adventures & Small Ship Cruises for 2023-2024

Relax in the sunny squares of historic Savannah

Boston, MA to Nassau, Bahamas

Boston - Nassau
16 Days from $6,649

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.

Bahamas Sailing Adventure

Nassau to Nassau
7 Days from $1,499

Board the luxurious sailing schooner Liberty Clipper in Nassau for a 7-day roundtrip cruise of the Bahamas, then explore the extensive Exumas archipelago and the Out Islands, including Eleuthera. Daily shore excursions include snorkeling, kayaking, and paddle boarding in crystal turquoise waters, or optional cultural and wildlife tours.

Relax on the sunny beaches of the Bahamas

Exploring the Bahamas’ Out Islands: Natural Wonders & Hidden History

Great Exuma, Bahamas Roundtrip
8 Days from $5,590

A unique 8-day journey into the islands' remarkable culture & wildness. The Bahamas is truly wild at heart. This archipelago of more than 700 islands—of which only about 30 are inhabited—is home to blue holes and thick mangrove forests, coral reefs, and spectacular beaches.

Roundtrip Jacksonville

Jacksonville to Jacksonville
12 Days from $3,759

Discover the charm of the Southern US coast on this 12-day cruise, round-trip from Jacksonville. Explore historic cities, beautiful sea islands, and the glittering beaches of the Bahamas on this unforgettable voyage aboard Ocean Voyager.

Boston, MA to Nassau, Bahamas

Boston - Nassau
16 Days from $5,599

Join the Ocean Navigator on a 16-day journey down the Atlantic Coast of the United States. Sail to Nassau, Bahamas, from Boston, Massachusetts. Visit historic ports such as Newport, RI, Baltimore, MD, Wilmington, NC, Charleston, SC, and Savannah, GA.

4 Best Bahamas Small Cruise Ships & Sailboats for 2023-2024

Ship Name	Max Passengers	From	Summary
Ocean Voyager	202	$3759	Skillfully designed to foster a convivial atmosphere, the Ocean Voyager invites you to relax and unwind as you discover the world's most remarkable … 0
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 … 0
Ocean Navigator	202	$5599	Perfectly designed spaces for every mood and every possibility the Ocean Navigator takes you on a splendid sailing discovery of some of the most … 0
National Geographic Sea Lion	62	$5590	The Sea Lion, sister ship of the Sea Bird, can reach places inaccessible to larger ships due to its small size, yet it comfortably accommodates 62 … 0