Frequent asked
What is the Jolly Roger?

The Jolly Roger is a unique, all timber-constructed 15th century Spanish galleon replica and a Cayman Islands heritage for almost a quarter century, offering romantic sunset cruises along Seven Mile Beach, family friendly swim & snorkel cruises with pirate entertainment & awesome adult party cruises with open bar, amazing party illumination & music entertainment. The Jolly Roger has been the leading ship during the famous pirates landing of the Cayman Pirates Week Festival.

What makes the charm of the Jolly Roger?

Setting foot on this beautifully ornamented 78 foot pirate ship lets you fall back in a romantic time of infamous pirates, fearless heroes and charming ladies and wenches. Enjoy an unforgettable cruise on this beautifully ornamented ship, with elegantly decorated inside captain's lounge, three timber masts, sails & rigging, antique cannon & a friendly pirate crew.

How many guests holds the Jolly Roger?

The Jolly Roger can hold over 50 guests - ideal for small to medium size party events. This ship has four (!) decks with a raised forecastle, which contains accommodation known as the bridal suite and a raised poop, which contains the officers’ saloon (captain’s lounge) and a small chart-room. The beautiful decorated captain's lounge offers shade and space for about 10 people to comfortably sit on the luxurious cushioned benches and more guests to stand.

I am getting easily seasick - how much does the Jolly Roger shake?

The Jolly Roger is the only single hull vessel on Cayman Islands that has sponsons attached to the hull port and starboard which increase the underwater area thus giving better stability - which means that you get less seasick! Furthermore, the Jolly has a heavy steel keel that increases further stability at all angles of heel, which makes her very stable = less seasick!

Do you offer private charters?

Absolutely! Aside scheduled cruises, we offer private charters for birthday parties, wedding ceremonies, bachelor parties, corporate events and more.

How much is a private charter?

Private charters start at $749 CI. For details please contact

Are you going out during the day?

Yes, during days we do our scheduled swim and snorkel cruises and private charters.

Are you going out during sunset?

Yes, our romantic sunset cruises along Seven Mile Beach are famous and an unforgettable event!

Are you going out during the night?

Yes, we do! Our beautiful illumination makes every night cruise an amazing experience.

Do you offer swim and snorkel cruises?

Yes, these are our favorites for families with kids, offering swim stops for jumping from our many decks and plank and snorkeling at breath-taking snorkel locations - but still... don’t forget to breathe!

Is your pirate ship kid/family friendly?

Absolutely! Families love our swim and snorkel cruises with pirate entertainment. The romantic sunset cruises are also family friendly.

What is included in a scheduled (ticket) cruise?

Our scheduled (ticket) cruises include a 2 hour cruise along Seven Mile Beach (sunset) or George Town (swim and snorkel), unlimited fruit punch and rum punch, (some include an open, unlimited bar), music entertainment and a friendly pirate crew making sure you will have unforgettable memories!

What is included in a private charter?

Our private charters can be customized and include a 2 hour 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!

Is there inside space on the ship?

We have a beautiful decorated captain's cabin that offers shade. It has space for about 10 people to sit but more can stand inside.

Can we bring our own music for our charter? And if so, what format does the music need to be in (CD, iPod, USB)?

Of course you can! Our music system has Bluetooth capability or you can plug in your USB drive.

Would it be possible for us to raise one of our custom flags for our charter?

Of course you can - make it an unforgettable memory!

We are planning a private pirate ceremony and would like to have a rough time guideline. Do you have an itinerary you follow for private charters?

Yes, we do have an itinerary. The charter begins with a safety tour and - depending on preferences and if kids on board - we do pirate entertainment (e.g. learn how to become a pirate with scrubbing the floor, some quiz etc) and then swim and snorkel stop. If you have specific wishes, please let us know - we try to make it happen!

Will we have a chance to stop and swim during our charter?

Yes, the Jolly Roger has several (four!!!!) decks and a plank with different heights above water level, offering a great choice for daredevils who want to do their jump of their life from over 15 feet height to just a little splash at 3 foot above water level.

What about guests who don’t behave?

They walk the plank!

How can we contact you?

Our email contact is