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Monday, Nov 02, 2026

Even without a ship, Cayman pirates take island

With the loss of their usual Pirates Week transport, buccaneers have to improvise

How do you mount a pirate invasion when you don’t have a pirate ship?

That was the challenge facing Cayman’s band of cutthroats this year as they planned their attack on George Town as part of the annual Pirates Week festivities.

The tall-masted Jolly Roger that has been a Pirates Week fixture for years was still undergoing repairs after running aground and partially sinking earlier this year. The Grosse Ile, a Canadian schooner that was recruited into service in the past, is no longer plying Cayman waters.

Darvin Ebanks, leader of the Bloody Bay Buccaneers, said Pirates Week General Manager Melanie McField came up with a scenario that solved the problem.

“Our pirate ship was sunk by the British Navy,” Ebanks said, sitting at the bar in Paradise Restaurant after successfully taking over George Town and putting Governor Martyn Roper in chains. “We were rescued by the catboats.”

In fact, to the surprise of many in the crowd lining the waterfront to enjoy the typically hilarious cardboard boat race Saturday morning, two catboats came ashore just as the adult division participants were lined up to launch their soon-to-be-soggy craft. Interrupting the contest, Ebanks and several other pirates leapt from the catboats as they hit the sand, declaring their ship had gone down at sea.

Moments later, they spotted a conveniently moored modern sailboat on the dock of Hog Sty Bay, commandeered it and sailed away. Two hours later they would return, the sailboat, with several pirate flags flapping from its rigging, and a trailing tender fully loaded with the scurvy, scowling band of ruffians the Cayman crowd has come to expect.

While it may have lacked some of the flair of past years, the energy level of the sneering, snarling, raiders – spouting threats threaded with far more Rs than any other letters in the alphabet – seemed just as potent as ever.

The landing had the added feature of a simultaneous performance by the 14-member Caymanite Synchro synchronised swimming team, decked out in gold caps, glitter and mermaid scale leggings.

At the same time, from beneath the surface of the water, a barnacled and seaweed-covered John Ferguson – aided by scuba divers – suddenly rose from the sea, stepping onto the beach as Davy Jones to applause from the crowd.

The invaders quickly captured the governor as his red coat army surrendered with little fight.

Roper said he was enjoying his second Pirates Week experience.

“Last year, we had just arrived,” he said, recalling taking office in Cayman. “At least now, I know what to expect.”

He lamented that his participation was limited.

“I wish they would let me get involved in the kidnapping,” he said prior to the parade. “I have a double to do that. They’re worried about my safety.”

Unless his double was a twin, it appeared Roper used his authority to get his wish to be hauled through the crowd by the pirates to a waiting pirate ship parade float.

He called Pirates Week is “a wonderful thing for our tourism industry”.

Nick Smith, 37, of London, was one of those tourists who came to enjoy the event. He said he timed his first-ever visit with friends living in Cayman to coincide with Pirates Week.

“We brought costumes specifically for this,” Smith said, sporting a tricorn hat and a gold brocaded coat. He described the festivities as “really happening”.

Steve Kidd, 42, was also visiting from the UK. His costume got a little wetter than he anticipated. Kidd was a member of the Pearl of the Poseidon cardboard boat crew, and fell into the water shortly after the boat was launched.

He remained floating offshore, cheering on the Pearl as it sped through the course. But just as it was rounding the rock in the middle of Hog Sty Bay and heading back to shore, well ahead of its closest competitor, Usain Boat, the race announcer reminded the crews that every member had to complete to course or their boat would be disqualified.

Kidd was left with only one option: swim for it.

He floundered through the water, weighed down by his regalia.

“This outfit was not made for swimming,” he said, once back on shore. “I lost my pants three times and had to put them back on. My teammates needed to pull me in the last five metres.”

By then, Usain Boat had finished, its crew surprised to learn that even though the Pearl had come ashore first, the trailing Kidd gave them the win.

“We heard we won and we were, ‘What?’” said Jess Hughes, 31, of George Town, captain of four-person crew that included her husband and another couple. “We just didn’t want to lose.”

More importantly, they didn’t want to sink. Hughes, an English teacher at Cayman Prep and High School, said some of her friends have built and raced boats in previous years, but none have made it back to shore.

During the week-long process to build their boat, she said, “We’ve been going through a whole roller coaster of emotions, thinking it was going to sink right away. We thought we were going to bring it home in bin bags.”

She looked at the intact vessel on the sand.

“I’m not sure what we’re going to do with it,” she said.

Other events featured during the festival included an opening night fireworks show on Friday, nighttime soca concerts, a pooch parade, a beach clean-up, an underwater treasure hunt for divers, a turtle release and an illuminated parade Monday evening followed by a closing show of fireworks.

Ben and Lorna Twidle, of Savannah, arrived in Cayman two months ago, but began preparing for Pirates Week before that, with costumes they ordered on Amazon.

“We knew this was coming, so we prepared for it,” said Ben Twidle, 27, as he and his wife walked the waterfront, impressed by all the activity. “It’s nice to see so much going on.”

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