Hoist the Jolly Roger


The daily to-do list aboard the Jolly Roger probably consists of mundane piratical activities like mixing grog, dividing the booty, marooning mutineers and counting down the days to Pirates Week.  

But before the rakish craft and her crew can take Hogsty Bay by storm in November, the Jolly Roger has to be repaired, cleaned and painted. An enormous undertaking which, until recently, could only be completed in Cuba. 

“We’ve always had to go to Cienfuegos, Cuba for dry dock,” said Harry Lalli, owner of Pirates of the Caymans. “That was the closest port to Cayman that had the ability to pull out a ship that size.” 

This year, however, the Jolly Roger was able to be hauled out of the water locally by Scotts Marine at the Barcadere Marina using a 100-ton travel lift installed just last year. 

“We’re very thrilled to be able to not have to risk the voyage across the sea to Cuba,” Mr. Lalli said. 

Anthony Scott, owner of Scotts Marine, explained that, even with the lift, getting the Jolly Roger out of the water was no easy task. 

First, the vessel had to be backed into a slip underneath the lift. 

“We only had about six inches on either side of her,” Mr. Scott said, explaining that divers had to help secure the straps underneath the hull to distribute the weight of the vessel evenly as it was raised out of the water. 

Despite fears from the Scotts Marine team that the sheer height of the ship’s stern would interfere with the lift, the 65-ton pirate ship came up without a hitch. 

Seeing a ship out of water is a little like seeing the submerged portion of an iceberg. Even with the top-heavy Jolly Roger, there is a great deal more of the ship below the waterline than above. 

“Everybody’s seen the Jolly Roger in the water but nobody knows that’s what she looks like out of the water and I think it’s quite a scene,” Mr. Lalli said. 


Careening: then and now  

Historically, pirates had limited access to dry docks. Pirates were welcome in few ports and so their ships had to be careened, a practice that involved purposely beaching the ship at low tide in order to replace rotten planks and scrape off barnacles. 

Even nowadays with the help of modern tools, maintaining the Jolly Roger requires a great deal of work. 

“It’s usually a good 30 to 45 days to get everything done properly and then it will be all shiny and ready for Pirate’s Week,” Mr. Lalli said. 

The ship will be power-washed to remove any barnacles and algae that have accumulated along the hull. Then, any rotting or damaged beams will be replaced and the hull will be painted with environmentally friendly anti-fouling paint to keep unwanted marine life from attaching to the ship. 

Because older anti-fouling paints frequently included toxins like lead, Mr. Scott said that any old anti-fouling paint stripped during the power-washing will be collected and disposed of by Scotts Marine to prevent pollutants leaching into the ground. 

Once the hull of the Jolly Roger is up to par, the work begins topside. 

“There’s a lot of work we would do while she’s in dry dock,” Mr. Lalli said, explaining that the maintenance team will then replace any wood above the waterline that is damaged, service the engine and the generator, and paint the vessel from stem to stern. 


The Valhalla  

The need for a local marina that could handle the large vessels was made clear last year when another one of Mr. Lalli’s rogue fleet, the Valhalla, was sunk off Cuba. 

The ship was severely damaged by Hurricane Sandy as the storm swept through Cuba four days before hitting the U.S. After languishing in the harbor for months, she eventually sank. 

“For me, it’s just a godsend to be able to not have to worry about sending the Jolly Roger away from the Caymans for its annual dry dock,” Mr. Lalli said. 

The only people who might miss the voyage to Cuba are the pirate crew of the Jolly Roger. 

“I don’t have sea legs so I’ve never actually gone across on a long journey on her but the crew, they love it,” Mr. Lalli said. “They have great stories of dolphins that swim beside it and over the bow for miles and miles.” 


The Jolly Roger sits on dry land at the Barcadere Marina while undergoing maintenance work in preparation for Pirates Week. – PHOTO: CHRIS COURT


  1. Loved the article on the Jolly Roger. Was sad to read that the VALHALLA sank in Cuba last year as a result of Hurricane Sandy! My family and friends have wonderful memories of fun, crazy times on the VALHALLA…

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