Issue 17.2: April / May 2014

Aloha, Ye Scurvy Dogs

Story by Michael Shapiro
Photo by Davis Bell

Alan Shepard must be the hardest-working pirate in show biz. As swarthy buccaneer Captain Hammerhead Alan, he fires water cannons at passing yachts, duels with six-year-olds armed with foam cutlasses and blasts sea shanties at surfers off Waikiki from speakers affixed to his masts. It’s all in a day’s privateering for The Treasure Seeker, one of Hawai‘i’s newest and weirdest tour boats.

If you’ve been down near Waikiki’s bounding main recently, no doubt you’ve seen a black, three-masted pirate ship terrorizing/ amusing anyone else out on the water. No ordinary pleasure cruise be this: Alan and his three-man crew—graduates of the University of Hawai‘i’s theater department all — engage passengers in hilarious pirate improv. Best to play along: They won’t break character and they’ll give modernity no quarter. “Yar, we be inconveniencin’ someone talkin’ to the future!” Captain Alan chastises a woman who answers her cellphone mid-skit. When the ship pulls alongside Jada II out for a cruise, first mate Smilin’ Jimmy Straw (ably played by Lavour Addison) opens fire with the water cannons. Everyone aboard Jada II answers the broadside with their backsides.

“Oh, we get mooned, flashed—anything you can think of—at least twice a week,” laughs Shepard, who landed a “dream job” as Hammerhead Alan by answering a Craigslist ad: “Looking to be a pirate? Call this number.” That led him to Greg Longnecker, owner of Xtreme Parasail, one of the state’s largest watersports tour operators. Longnecker was looking for something a little less extreme: He bought an old salmon fishing boat in San Diego, retrofitted it to resemble a corsair, sailed it to Honolulu and launched Hawaii Pirate Ship Adventures.

The Treasure Seeker has been running ninety-minute cruises since last June: The adults-only BYOB night cruise is for those yearning to commit higher crimes on the high seas, but the day sails are mainly for kids, who enjoy the adventure almost as much as the actors, like the climactic moment when Captain Alan hauls up a treasure chest full of plastic doubloons moored to a buoy. “The kids’ eyes light up,” he says, momentarily dropping his accent, “and they think it’s just the greatest thing ever.”