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Sailing Story: Corey Roy

Smiling man with sunglasses on a boat, quote about sailing above, Virgin Islands charter logo in corner.Corey Roy has always loved the water. In part, that’s what drew him to join the Navy. While his time in the military was perfect for his engineering and science mind, he realized it wasn’t exactly the best way to enjoy the beauty of the water. 

“I joined the Navy to see the ocean. Then I was stuck in a black tube and never saw anything,” Corey laughed about his experience working on a nuclear submarine. “Unless you are one of the people working on the bridge and doing the navigation, you’re not really seeing anything anyway.”

Corey spent a total of two and a half years underwater during his time in the Navy and once spent 42 straight days in a submarine before resurfacing. Luckily, he was able to find another way to enjoy the water while still active duty— sailboats!

“I learned how to sail in 2013 in Norfolk, Virginia on the Chesapeake Bay,” he explained. “I absolutely loved it.”

However, his introduction to sailing was a far cry from the luxury yachts of the Virgin Islands. Corey’s friends introduced him to sailing schooners, the historic tall ships with large fore-and-aft sails. 

“Within a year of learning how to sail I started volunteering on some of those tall ships,” Corey explained. Then, when he got out of the Navy in 2015, he began working on tall ships full-time.

He received his first coastguard license and then his captain’s license. Before long he was the chief mate on Schooner Virginia.

“Oh this could be a real career,” he remembered thinking about his first job with health insurance and retirement outside of the Navy. Then, his sailing career took yet another turn while he was at a local nautical festival on his own 47 foot schooner. 

He was looking for extra work and had docked next to some people looking to hire an ASA instructor.

“What’s ASA?” he had asked. Then, as it was explained to him he remembers thinking, “That’s kind of what I do every day [as a Chief Mate on Schooners]. It’s a lot of education and I was in charge of training our crew.”

In 2022, he received his American Sailing instructor certifications and traded in the tall ships for sailing yachts.

“The scope and hardware is the difference,” Corey said. “The hands-on experience of being on a sailing vessel is the same no matter where you go.” 

Corey described how you tack and jibe is virtually the same on any sailboat but what draws people to the vessel is different.

The historic factor gets people involved on tall ships. It’s nostalgia,” Corey said. On sailing yachts he notices it is more about the vacation element and says it’s, “cool seeing people do it for their own knowledge or enjoyment.”

Corey says those are aspects of teaching students how to sail luxury yachts in the Virgin Islands that he truly enjoys himself as well.

“I especially love St. John. That’s probably my favorite place I’ve been because it’s a National Park and you get a lot of places that are protected,” he said. “I really like just passing what I know on to people so they can go experience what I have.”

From submarines, to tall ships, and now to catamarans in the Virgin Islands, Corey is happily tied to the water for life. A perfect place to be for a man who believes “a nice sunset never gets old.”