Fifteen little pirates complete with swords, eye patches and a full vocabulary of sea-worthy words boarded the Sea Gypsy in the Oak Bluffs Harbor on a recent morning. Under the capable hand of Capt’n Flint, young pirates with names such as Cutlass Cole, Wild Man Willie and Osprey Olivia discovered a treasure map, fought a fierce water fight with a treasonous pirate and hauled up a treasure chest.

Jeremiah McCarthy: once feared on land as a lawyer, now feared at sea as a pirate. — Mark Lovewell

In approximately an hour, the pirates returned to the mainland, handfuls of treasure safely stored in zip-lock bags and memories of the adventure locked away in their heads.

But for Jeremiah McCarthy, the pirate life is the life for him all summer long.

Mr. McCarthy grew up on the Vineyard and before taking on the moniker of Capt’n Flint he was a lawyer, practicing at a firm in Edgartown.

“I like the uniform better,” Mr. McCarthy said referring to his switch from legal work. “I’m barefoot 95 per cent of the time, and I prefer that to patent leather.”

Mr. McCarthy was making the transition from law to taking over the management and ownership of Dockside, an indoor market that borders the Oak Bluffs harbor, from his parents, when his wife Catherine (Lady Pearl in pirate circles) suggested pirating. She had just been aboard a similar pirate cruise and thought it seemed like a perfect fit for the business.

Capt'n hauls in some booty. — Mark Lovewell

They had the dock space, the imagination and the dramatic flair, so the McCarthys commissioned a pirate ship, toured other pirate cruises and created Pirate Adventures Martha’s Vineyard.

On and off board, Capt’n Flint is assisted by his crew, including manager Coral Castaway, plus Rudder and Throttle. Beyond trading an office for the sea, Pirate Adventures also provides a child-oriented daytime activity in Oak Bluffs. Mr. McCarthy’s experience with programing children’s activities comes from being a dad, he said. With two kids aged four and seven, he knows how delicate family vacation time can be and the importance of imaginative play.

On a recent trip, two-and-a-half year old Aye-Aye Abel (all the kids get official pirate names) donned his eye patch and was ready to go. Young Aye-Aye is an experienced pirate, having set sail three times already.

“We’ve done it in the sun and in the rain. It’s fun no matter what,” said Aye-Aye Abel’s mother, Nina Kiendzior.

Though guided through the adventure by the crew, the little pirates are the star players in the trip, and each one gets an individual part. Mad-Dog Mary was sent to ask Capt’n Flint if he had the last piece of the map puzzle they were putting together. The little pirates chanted, “I hope he has the piece,” while crossing their fingers.

“He did,” Mad-Dog Mary announced, running back to the bow triumphantly with the final piece of the map.

Aboard the Sea Gypsy with Pirate Adventures. — Mark Lovewell

“The whole idea is they are figuring it out,” said Mr. McCarthy. Whether it’s assembling the map, spotting the floating bottle or figuring out clues to the treasure, the kids are at the steering wheel.

Mr. McCarthy, who is drawn to the whimsical elements of being a pirate, is often described as a kid at heart. It’s a description he embraces.

“Basically I own an ice cream and candy store and I play pirate all day,” he said.

To book a pirate adventure visit

More photos of a trip to sea with Pirate Adventures.