Best Islands to Live On: Expat’s Life on St. John, USVI

December 12, 2012
Jamison Witbeck
Jamison Witbeck on St. John, USVI Courtesy Jamison Witbeck

Jamison Witbeck didn’t intend to move his family to St. John. Not again. He’d run a boat charter business in Maho Bay, only to move to South Carolina to pursue a conventional life. While there, he sold a catamaran he’d built to a buyer in the Virgin Islands. Well, he tried to sell it. “The story from there takes a few turns,” the 38-year-old says in the kitchen of his Fish Bay home. His wife, Claire, flips blueberry pancakes for their three kids while Jamison pours a little maple syrup into his Caribbean coffee.

Q: What’s with the syrup?
A: I grew up in a small town in Vermont. I’ve gotta represent.

Q: All right, the boat. What happened between Charleston and the USVI?
A: It’s a 50-foot wooden catamaran that I built with my brother, Ryan. We hired a British captain to deliver the boat to a guy in St. Thomas, and he left ahead of a winter storm. He was out there in the Bermuda ∏riangle, with 30-foot seas and 50-knot winds, microbursts, lighting storms, a little bit of hail. Nasty stuff.


Q: And then what happened?
A: The boat was taking on water, so the captain radioed to the Coast Guard, and he and his crew were airlifted off.

Q: No captain, no crew, no boat.
A: Sort of. The boat went missing for five days. But with the help of aircraft we found it drifting two miles from the outer wall of the Gulf Stream, nowhere near land. Amazing that it ran. Ryan and I motored back to the U.S., fixed it and sailed it over to St. Thomas ourselves.

Q: No boat-delivery guy this time?
A: No way. That sail changed my life. There was nothing out there but dolphins, whales and flat water. After all that, when we arrived the deal fell through. We decided to keep the boat and tell my family to pack up — we’re moving back to the Virgin Islands.


Q: A second move. What was that like?
A: Easier than the first time. When we originally moved to St. John, we didn’t have enough money for a beat-up car. My wife was working, so I was Mr. Mom at my charter job — driving the boat with my daughter in a carrier and stowing six bottles of milk in the cooler.

Q: This time was different because …?
A: We were smarter. The biggest question was school. There was a chance we’d go belly up, and have to pull the kids away from their friends again. We didn’t want that. So we home-school.

Q: Was it the right move?
A: Oh, yeah. There were a lot of advantages. Claire would help the kids with the hard book work from 8 to 12, then they’d have the afternoon to hike through the old sugar-mill plantation ruins or go to Cinnamon Bay to relax.


Q: Sounds like the life. Charter boat for work, blueberry pancakes for breakfast.
A: Parents can be anywhere in the world and ask, “Am I doing the best thing for my kids?” At least here we can train them to do more with less.

Q: Give some examples, please.
A: A sailboat: Put up some cloth and see how far it takes you. A treehouse: proof that all you need is six feet of dry space.

Q: Wasn’t it hard to give up your lifestyle?
A: It sounds odd, but figuring out what to do with all our stuff is one of the hardest parts. I say just give it all away. People here prove that you can live on whatever an island gives you.


Q: Anyone in particular?
A: Yeah, there was this scruffy guy who came on my boat with just a tent and a backpack. He asked me to leave him on a deserted island in the BVI.

Q: And did you?
A: Well, the guy said, “I’m gonna swim out to a moored boat and say, ‘I’m a castaway! I need some food.'” So I left him. A week later I sail up and there he is, sunburned and scruffier, saying how he was given a stateroom in a megayacht.

Q: Your boat is named Kekoa. Why?
A: In Polynesia kekoa means “the brave one,” so it’s paying homage to ocean-going travelers. People assume we named the boat after the storm, but it just worked out that way. I’m glad kekoa didn’t mean “Sinks Like a Stone”— then we might never have gotten the boat back. And I might not be back here.

Discover more about the USVI in our new Best Islands to Live On: USVI Guide.


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