Come sail Key West’s most photographed ship – the Jolly II Rover, a square rigged topsail schooner! A Key West sailing adventure aboard the Schooner Jolly Rover takes you back in time on a classic 80’ coastal topsail ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly Rover adventures. Complete your Key West vacation with a Key West boat tour on a tall ship.

Schooner Jolly II Rover Key West Sunset Sail 

Sunset Sail

A top Key West attraction is the Jolly II Rovers famous “Red Sails in the Sunset” 2 hour sunset sail! Take in a memorable sail of Key West’s most famous sights while the sun works its magic turning the sky brilliant colors. With our distinctive red sails and being the only square rigged tall ship in Key West, the Jolly II Rover is the focal point as we sail past the Mallory Square Sunset Celebration. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic tall ship sailing experience.

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Schooner Jolly II Rover Key West Day Sail 

Day Sail

Our daily 2 hour afternoon sailing tour fits perfectly into your Key West sightseeing trip. Enjoy an exciting Key West sailing adventure on the glistening crystal blue waters, with the Rover’s signature red sails flying! Look for the abundant Florida Keys wildlife both in the air and sea. Find your inner pirate and join the crew while you hoist the sails, steer the ship and fire the cannons!

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Private Charters

Searching for a truly unique Key West sailing experience that is all your own? Charter your own private Key West tall ship sailing adventure. Whether its a few hours to celebrate a special event or an all day adventure, tell us where you want to go and what you want to experience, then climb aboard! For memories of a lifetime, charter a sunset wedding or an overnight excursion. Boca Grand is only 12 miles outside of Key West and is in a world of its own. You can even charter the Jolly II Rover for a private party dock side or anchor overnight experience.

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Land And Sea Combo Tour

Experience this Pirate Tour adventure by Land and Sea. This tour will feature some hearty tastings of classic locally inspired Surf and Turf Food and Drink rations to satisfy your hunger and thirst. You will spend 2 hours on land and 2 hours at Sea accompanied by your local Pirate Guide who will bring to life the past and present beauty, simplicities and complexities, the colors and the characters of The Historic and The Iconic Key West Florida.

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