Ahoy mates! Pirate Adventures is underway in Oak Bluffs

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The young crew uses water cannons to repel Bootstrap, a rogue crew member. — Photo by Michael Cummo

The Dockside complex in Oak Bluffs hosts a number of familiar Island businesses such as Hy-Line Cruises and Coop de Ville restaurant. However, a recent investigation by the Times has discovered an unlikely addition to the waterfront commercial property’s tenant roster: a nest of pirates.

The Oak Bluffs Police Department has been hesitant to provide much information on the pirates, citing an ongoing joint investigation with the U.S. Coast Guard into what they described as a recent spate of “coastal marauding.” They did disclose that a vessel called the Sea Gypsy was of great suspicion. After a bit of sleuthing, The Times was able to find a square-rigger berthed in Oak Bluffs Harbor, bristling with cannons and flying a Jolly Roger. A closer inspection of the vessel revealed the name Sea Gypsy emblazoned on the prow, as well as twin Yamaha outboards off the stern. Evidently the Sea Gypsy wasn’t subject to the vagaries of the winds, as it might otherwise seem. Pirates are crafty.

After what appeared to be a bit of flag semaphore with cocktail napkins, a bartender at Coop de Ville was able to summon the captain of the Sea Gypsy for The Times to question. The gentleman who came forth wore a tricorn hat, Tortuga pants, high-buckled boots, and several other articles of clothing not often seen outside Renaissance fairs.

He introduced himself as Captain Flint and, after putting a hand atop the cutlass at his waist and grinning devilishly, said he’d arrived at “terms” with the owners of the Sea Gypsy, Catherine and Jeremiah McCarthy, terms that kept him at the helm and them free of perforations. He said that those terms would remain in force for the foreseeable future.

Captain Flint claimed times were tough for pirates. For example, the last Hatteras cruiser he “appropriated” sank before he could flip it to his cousin in Port Royal. He also owes some cutthroats on Chappaquiddick his body weight in silver coins (he’s been dieting). Strapped, he’s resorted to tourism. In fact, five times a day, he’s taking children out on the Sea Gypsy to give them a taste of the swashbuckling life. The kids come in looking too clean-cut for Captain Flint, so he decorates them with tattoos and outfits them with bona fide pirate gear before letting them aboard. For about 70 minutes he and his mates sail the Sea Gypsy out of the harbor and down off Inkwell Beach, teaching the youngsters the tricks of the trade. Inevitably there’s action, suspense, and of course, adventure. Captain Flint claimed to be a magnet for such things. He also admitted, with a bit of a scowl, that the kids seem to have a lot of fun.

“Our first day we had two trips, one of which was sold out. It was amazing. We had parents and kids gushing over how much fun they had,” the captain said.


Pirate Adventures Martha’s Vineyard, 12 Circuit Avenue Extension, Oak Bluffs. Now operating a full schedule through Labor Day, with up to five sails daily (weather permitting). Tickets $32 for all pirates, regardless of age. Reservations required. All Dukes County residents receive a 20 percent discount for locals and their kids and grandkids. Visit mvpirates.com, or call 508-687-2739 for more information.