• 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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  • Spend your time with style on the
    Tuscany Yacht

    Indulge yourself and spend a relaxing time tasting finest wines on a classy yacht along the breath taking Seven Mile Beach.

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  • A must see experience when visiting Cayman Islands
    Cayman Pirates

    Bring the kids and join us for an afternoon Pirate Adventure or chase the sun when setting at the breath taking Seven Mile Beach.

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Our fleet
From Pirate Ships to Luxury Yachts…
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

The Tuscany

The Tuscany is a beautiful yacht, built in a classic 60s style, that enchants every passenger with its charm and magic. Up to 40 guests may enjoy luxurious parties, wine tasting events, sunset cruises or maybe you just want to have some special moments alone with your loved one? Enjoy the crystal clear turquoise waters during the day, the breath taking sunset along the legendary Seven Mile Beach or let yourself be covered with glittery kisses of millions of stars smiling upon you in the evening.

  • Jolly Roger – party into the sunset
    Booze Cruise

    Want to have REAL fun? The Jolly Roger is the perfect vessel to get it moving. Get many drinks on the house while the DJ gets you and your friends in the real mood.

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  • Jolly Roger – Pirate fun with snorkel stop
    Little pirate

    Come with your kids on the Jolly Roger and they have the adventure of their life to become a pirate! But be aware – it’s not easy to deserve the title “Caribbean Pirate”!

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  • Tuscany – fun for 3 or more hours
    Birthday Party

    It’s your birthday? The cake and wine are on the house! Come and party with us on the beautiful Tuscany yacht surrounded by turquoise crystal clear water that invites you to dive in.

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  • Jolly Roger – excitement at dusk
    Sunset Cruise

    Follow the setting sun at one of the most beautiful beaches – Seven Mile Beach. This experience remains unforgotten.

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  • Tuscany – unforgettable moments
    Wedding Party

    Where could you imagine a more memorable wedding party than on a classy, luxurious yacht? The Tuscany makes sure you won’t forget this time.

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  • Tuscany – get really classy!
    Wine Tasting

    Enjoy a variety of selected fine wines in an environment that makes your taste buds enjoy every sip even more. Aside professional background information and stories by our wine connoisseur, every served wine is accompanied by a variety of delicious cheeses and other side dishes that complete the tasting experience.

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Make your reservation

Jolly Roger Cruises types:

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Step 1: Choose cruise type and date

Step 2: Set options, discounts, etc

Step 3: Final prices review

Step 4: Finish booking
Client
Reviews
  • Maria Lores, Los Angeles

    We are from California, so my kids are not easy to impress by sun and beach. I was lucky to find the Jolly Roger. After the cruise they did not want to leave…

  • John Benson, New York

    One of my finest experiences here in Cayman. I've spent four lovely relaxing hours on the yacht.

  • Steve Grant, Detroit

    I had the best time of my life! Highly recommended!