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