Jolly Roger in Grand Cayman

Pirates of the Caribbean: Treasure on Grand Cayman

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A year ago, Grand Cayman had a well-known, highly-attended pirate festival—but no pirate ship. This year, the times, they are a changin’. Because, folks, the Jolly Roger is now in business.

Jolly Roger in Grand Cayman-1


Earlier this year, a pair of guys both named Chris bought the dilapidated ship and gussied her up.

Arrrr! A Pirate Adventure in the Cayman Islands

Right after I landed in Grand Cayman last month, I drove myself straight to the George Town harbor where the Jolly Roger was parked. For the Travel Mindset project I was working on, they had me booked to go out on an afternoon cruise. Well, the Jolly Roger’s schedule is largely determined by the dozens of cruise ships that visit Grand Cayman each month, and I lucked upon an afternoon when there were none in port. Which means I had the ship to myself. Lucky girl, right, being taken out to the high seas—ALONE—by a band of swashbuckling pirates? I was OK with it.

Arrrr! A Pirate Adventure in the Cayman Islands

They gave me a safety briefing as we pulled out and then a sneak peek of some of their routine (which typically includes having kids swab the deck and then tying up their parents before throwing their fellow pirates overboard after a sword fight!).

Arrrr! A Pirate Adventure in the Cayman Islands

After I got a bit of a preview of what a typical trip might entail, we all settled in with our rum punch (included in the cost of the pirate cruise) as we sailed alongside Seven Mile Beach and got to know one another.

Arrrr! A Pirate Adventure in the Cayman Islands

There’s Jaz—chief wench, she told me—who was new to the company, having just come over to the Caymans from the UK a couple months prior. She manned the bar during our two-hour tour.

Arrrr! A Pirate Adventure in the Cayman Islands

Bebe is a divemaster who came over from Honduras, where he previously lived in the Bay Islands. He and I did a little underwater exploration and some free diving once the captain anchored the ship.

Ryan, a transient Floridian working in real estate, was passing through Grand Cayman for a few months, mainly to help out his buddy Chris. As he said, “you don’t say ‘no’ when someone gives you the opportunity to become a professional pirate!”

Arrrr! A Pirate Adventure in the Cayman Islands

Then there’s the Cap’n … who I only knew as the Cap’n. A native, he made sure our ship safely navigated the high seas of the Caribbean as the rest of us downed some rum punch. He traded some of the ship’s beer supply for fish—which was tossed directly from one boat to another—as a pair of fishermen motored passed us.

Arrrr! A Pirate Adventure in the Cayman Islands
Arrrr! A Pirate Adventure in the Cayman Islands

And lastly, there’s Chris, one of the two owners who is essentially the public face of the brand (the other Chris, I’m told, keeps things running in the office). A native Floridian, he and his wife had been in the islands a few years already—he was a bar manager at Margaritaville—when he and Other Chris decided to purchase the aging ship, gussy her up and launch their own pirate brand, the only one on the island. It’s every 20-something’s dream, right? I’d say they struck gold—or maybe stumbled upon buried treasure?—when they dreamed up their company.

Arrrr! A Pirate Adventure in the Cayman Islands

I had such a blast spending a few hours with this motley crew, swimming and snorkeling and doing flips off the bow and getting to know each of them, that I seriously considered going back for one of their sunset adult booze cruises later in the week. Unfortunately, the timing didn’t work out, but this will be one of the first stops I make when I return to Grand Cayman with SVV, hopefully something I can make happen soon (because the diving! Good Lord Almighty, the diving! just wait until I tell you all about the diving!).

Arrrr! A Pirate Adventure in the Cayman Islands
Arrrr! A Pirate Adventure in the Cayman Islands

Because who wouldn’t want to be stranded out at sea with these guys?

Starting tomorrow, Grand Cayman celebrates its annual 10-day long Pirates Week Festival, full of costumes galore, events, fireworks and even a mock pirate invasion. Now, I’m all about themes and anything kitschy, so obviously, the discovery of such a fest has quickly propelled this to the top of my travel to-do list.

Jolly Roger in Grand Cayman

Who out there has participated in a pirate festival before? Is it every bit as fun as I imagine it to be? (You better say yes, or my friends aboard the Jolly Roger will have you walking the plank!)

  • November 6, 2014

    Haha that one photo of the guy diving! Cracks me up 🙂

    • November 7, 2014

      He was the biggest goofball of them all!

  • November 9, 2014

    This looks like so much fun! I’d love to do this trip, actually I’d love to become a professional pirate for a while. What a great job!

  • February 19, 2015

    I just wanted to say that i Becky and my four children had a blast on the grand cayman pirate a adventure. The pirate Chris was really good with making sure we had a great time. I just wish I could of gotten to know him a little better for he was super sweet. It would mean a lot if your company would send him this review . We were there on the ship on Friday February 13 2015 with carnival ship Splendor. Thanks again sincerely Becky Decker from sartell Minnesota

    • February 19, 2015

      I just forwarded this to them! SO glad you guys had a great experience with the Jolly Roger. I also adored Chris and the whole team and would love to go back and spend more time with them all soon.

  • May 20, 2015

    Amazing challenges once and for all, you just gotten any brand fresh readers. Quantity people suggest of your create which you made some . blue cruise turkeydays in the past? Any specific?

  • September 16, 2015

    Trying to book with you and your website won’t let me. Can’t find a phone number for your company. All posts are from 2014. Are you closed?

  • November 6, 2015

    Late to this post, but wow this looks like a good time! Even better, I’ve now learned about the Pirate Festival, which has just rocketed up my “must do” list! It’s been a long time since I’ve been to the Caribbean, but it looks like it’s time to go back. Thanks for sharing!

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