A pirate's life for me: On deck with Hilton Head's preeminent privateers

A pirate's life for me: On deck with Hilton Head's preeminent privateersAndy Carpenter remembers visiting the island as a kid with his family and being faced with two options with which to busy himself: play some golf, or go to the beach. “A vacation that does not actually make,” says Carpenter, now a copy editor and page designer at The Island Packet.

Hilton Head has always been big on passive summertime activities, happily bypassing the tacky approach to tourist amusement embraced by, say, Myrtle Beach’s cheesy theme parks and ugly water slides.

But lately, the island is finding new ways to balance the excitement of family amusement with its natural amenities — and even adding a few educational opportunities as well. Pirate tours are the hot thing on the water this summer, offering droves of eager children the adventure of a sea voyage with their own salty buccaneer guides. The tours let kids be the crew on a ship as it explores the local waters, hunts other scalawags in the sea and searches for treasure.

And now — after answering an ad on Craigslist — Carpenter gets to put “professional pirate” on his resume. He’s one of the pirates you’ll see leading the boatful of young buccaneers on the Schooner Welcome pirate sail tours out of Shelter Cove.

“It’s one of the only jobs when everyone is excited to see you,” he says. “It’s like driving the Oscar Meyer Wienermobile.”


More Monthly: Arrrr there pirates in Hilton Head's history? (Sorry. So very sorry.)


These entrepreneurs might have a little Johnny Depp-fueled movie franchise to thank for part of their popularity, but it’s the pure fun of acting the pirate part that keeps it going.

“It’s such a good family destination: beautiful water, a calm area. But there’s really not a lot for the kids to do here,” says Patrick Coughlin, owner of the Pirates of Hilton Head tour, which departs from Harbour Town. “Finding treasure: What little kid doesn’t like that?”

The Black Dagger, Coughlin’s brand-new, custom-built boat, departs on a 75-minute tour from the Harbour Town pier. Before getting in the boat, kids get ready for the pirate experience by donning pirate-style hats, bandanas, tattoos and scarves and learning the finer points of pirate lingo.

“We make them the crew when they’re out there,” Coughlin says. “The whole experience is making them do everything.”




Photos / Mark Staff


The climax of the voyage is an attack on a pirate named Stinky Pete, who, the crew learns, stole the key to the treasure. The battle flag goes up, pirate songs are sung and an assault is launched from the ship’s mounted water cannons.

Coughlin, who previously owned a chain skate/snow/surf shops and then a medical equipment company, was originally looking to start the pirate tour near his home in New Jersey. But the mix of natural beauty, vacation crowds and a touch of local pirate lore made Hilton Head the perfect fit, so he moved the operation south.

“Being a pirate is something that’s just really easy to jump into,” Coughlin says.


Carpenter, of the Schooner Welcome, moved to the island In February 2009, but needed some extra work to help cover student loans (“Looking for summat to help me in regards to booty,” as he phrased it on his cover letter). “It was something I’d have kicked myself for not applying for,” he says.

To get into character, he starts assembling his multi-part pirate outfit, which includes old necklaces and thrift store pants that have been shredded up.


Where to be a pirate


“As you’re sort of changing into this costume, piece by piece, you start to feel like a pirate,” he says.
The role locks into place with the final bandanna and a fake gold tooth. “By the time that’s on, I’m in the zone,” he says.  He’s got the hang of the pirate lingo, but parroting the gruff pirate brogue can be trying.

“It sounds like I’ve been chain-smoking,” he says. “The first couple weeks of getting back into it, I drink a lot of tea. Otherwise it just shreds the vocal chords. You start sounding like Gollum.”

The kids on the boat get a goodie bag with a mix of pirate stuff: swords, bandannas, and, eye patches, and they pick a pirate name. Once in the water, Carpenter and the other characters discuss lore, play games and look for other boats.

“It’s something you can do for kids and get them out on the water,” says Matthew Milling, who owns the Schooner Welcome.

In the offseason, Milling uses the boat to give tours for the Lowcountry Maritime Society, a non-profit group Schooner Welcome started to teach kids about local waters. “We really tried to make the boat an environmental ambassador to the Lowcountry,” he says.

The adventure and allure of the pirate lifestyle is hard to resist. “When I was a kid, you couldn’t pay me to go on a sailboat,” Carpenter says. “But if you told me I was going to get to be on a pirate ship and be a pirate an hour and a half, I would have signed right up.”