Becoming Captain: Living A Dream In The Virgin Islands

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Coy Theobalt's sailboat, Gypsy Wind. (Courtesy Coy Theobalt)
Coy Theobalt's sailboat, Gypsy Wind. (Courtesy Coy Theobalt)

Coy Theobalt was first enchanted by the open sea when he was 8 years old. After a fishing trip with his father, Theobalt says he made up his mind: He wanted to become a boat captain.

But it wasn't until years later that Theobalt actually became "The Captain."

After 17 years of work in therapy and counseling, Theobalt was tired of working in an office. He took his corporate leadership development practice to the field (and ocean), guiding outdoor excursions, boating trips and more.

On one visit to St. Thomas in the spring of 2005, Theobalt found his calling.

"I was standing at a gas dock about to pay my gasoline bill for the boat, and I picked up this little island rag and opened it up, and there was this boat and this business, and everything just spoke to me right then," Theobalt says. "I just looked at that and said, 'I think that's my boat.'"

(Courtesy Coy Theobalt)
"The Captain" at work. (Courtesy Coy Theobalt)

By November, the move from Colorado to the U.S. Virgin Islands was complete. But adjustment to island life took some time.

"When people come to the islands, you're either gonna have to slow down or you'll go crazy," Theobalt says.

When he finally got his new charter sailing business off the ground, Theobalt had found peace.

"Just sitting in the cockpit and leaning back and looking at the sky and looking at the clouds, and the water, and the sun, and just saying, 'Wow, this is my new life, and I love it,'" he says.

His business flourished ... at first.

But on one trip through the Caribbean, Theobalt — and his boat — were in danger.

"It was one of the most terrifying 25, 30 minutes of my life," he says.

Click the play button next to the headline at the top of the page to hear the full story. And learn more about Coy Theobalt's life as a charter captain in St. Thomas in his book "Gypsy Wind Speaks."

This segment aired on January 14, 2017.


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Gary Waleik Producer, Only A Game
Gary Waleik is a producer for Only A Game.



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