• Come on board of the legendary pirate ship

    Cayman Islands

    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, rum punch, unlimited fruit punch and water. Bar half price.

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  • Relax and good time

    Sunset/Dinner Cruise

    Sunset sail along Seven Mile Beach, unlimited rum punch, fruit punch, water, bar half price.

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  • End the week with a party

    Booze Cruise

    Unforgettable party cruise with amazing lights, music entertainment, unlimited open bar (non- and alcoholic beverages) and FUN!

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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 an 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 Dinner or Cocktail 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.

Private charters – starting at $649 CI!

Have your own pirate ship for a few unforgettable hours! Our private charters can be customized to your needs and include a 2 ½ hours cruise (which can be extended - 3, 4, 5 or more hours) unlimited fruit punch and rum punch, open/unlimited bar, food catering, music entertainment, photographer, pirate entertainment with a friendly pirate crew making sure you have your event of your life! If you have specific wishes, please let us know - we try to make it happen.


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!