Sailing Story: JT Quinn

“I had no idea how to right the boat and threw a full tantrum in the water,” Captain JT laughed. “I swore I’d never set foot on a sailboat again. Looking back, that messy first sail makes me laugh—and it serves as a reminder of how far I’ve come and how much I loves being on the water today.”

The Virgin Islands offer some of the best sailing grounds in the world, making them an incredible place for JT to teach. The steady winds and calm anchorages create ideal conditions for learning the fundamentals, while the vibrant scenery and island culture keep every experience exciting. What truly motivates him, though, is helping students build a sense of confidence that lasts long after the course is over—confidence not just in sailing, but in themselves.

“The sea has a way of showing us what we’re capable of, one tack at a time,” he said.

One of JT’s favorite snorkel spots is Cow & Calf Rock in the USVI.

“It’s not a destination that’s always accessible—conditions have to be just right—but that’s part of what makes it special,” he explained. “When the weather cooperates, the water comes alive with schools of tropical fish, colorful coral, spotted eagle rays gliding through the shallows, and even small reef sharks that keep a respectful distance. For many, it becomes an unforgettable highlight of the week.”

JT’s goal as an instructor is to develop confident sailors who not only grasp the technical aspects of sailing but also know how to truly enjoy it. He strives to help students feel capable at the helm, excited to explore the islands, and ready for whatever adventure comes next—whether it’s navigating through a tight anchorage or hunting for lobster in a secluded bay.

“I encourages students to see the course as a learning vacation. There’s no need to arrive with anxiety about the material or fear of handling the boat,” he said.

JT ensures that everything is done safely, in a relaxed and supportive atmosphere. Students are encouraged to ask questions, build skills at their own pace, and have fun while growing their confidence on the water.