• Come on board of the legendary pirate ship
    The Jolly Roger

    Travel back in time and experience unforgettable moments as a Caribbean pirate on an authentic pirate ship in one of the most beautiful maritime areas of the world.

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  • Pirate adventure time
    Day Cruise

    Snorkel/swim tour along Seven Mile Beach, with unlimited open bar!

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  • Relax and good time
    Sunset Cruise

    Sunset sail along Seven Mile Beach, with unlimited open bar!

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  • End the week with a party
    Booze Cruise

    Sunset sail along Seven Mile Beach, unlimited drinks…yes: UNLIMITED!

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About Jolly Roger
The Jolly Roger

The Jolly Roger is a two-thirds replica of Christopher Columbus' 15th century Galleon Nina, which crossed the Atlantic on three occasions. The Jolly Roger was privately commissioned and built in 1986 in St. Petersburg, Florida, and christened the Lady Barbara. The original owner had such strong feelings for his wife that he had the ship's figurehead sculpted in her likeness. To this day, Lady Barbara still graces the bow of the Jolly Roger. Then to the current owner, who is passionate about sailing as Pirates, restoring her to her full glory and keeping the dream and imagination of Pirates and chasing the sun alive.... THE JOLLY ROGER

Pirates of the Cayman Islands

Get in touch with your inner Pirate! What's That?... Don't have one? Well then you can borrow a few of ours as we sail along Seven Mile Beach aboard a Pirate Galleon. Bring the kids and join us for an afternoon Pirate Adventure or chase the sun along the beautiful Seven Mile Beach coastline for a Sunset Cruise.

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Jolly Roger Pirate Ship

Jolly Roger Cruises types:

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Private Charters

How would you like to have the Jolly Roger all to yourself?

You can with our private charter program.

Ever dream of sailing the open ocean and being a pirate on your very own pirate ship? Want to kick back, stretch your legs and enjoy a lazy afternoon on board the largest sailing vessel in the Cayman Islands? Or your very own Sunset or Full Moon sailing!

Great for birthdays, family reunions, office get-togethers, corporate events, New Year’s, anniversaries – and more!

Contact us and we’ll help you plan that special event down to the smallest detail.


Like a fairy tale come true. Take your vows at sunset framed by the Cayman sunset and crystal blue waters of the Caribbean.

Charter either of our ships for your friends and family, or tie the knot on a private section of the deck on one of our regularly scheduled cruises. We can even provide M.C., if you require!