American Sailing · video

What this video covers

Cory Roy transitioned from a 10-year career as a nuclear propulsion engineer on the USS Springfield to a full-time professional sailor and American Sailing Association instructor.Watch His maritime background includes working on tall ships in the Chesapeake, specifically the 105-foot Schooner Alliance and the Schooner Virginia.0:52 In 2022, he and his wife purchased Winsong, a 47-foot wooden schooner built in 1954 in Nova Scotia.1:49 Roy currently balances seasonal work, teaching for Go Sail Virgin Islands during the winter and operating tall ships in the Chesapeake during the summer.3:02 He serves on the race committee for the Great Chesapeake Bay Schooner Race.3:05 Roy advocates for aspiring sailors to gain experience by visiting local marinas and volunteering as crew on boats, noting that he has never been denied an opportunity when asking to help on a vessel.3:59

More from American Sailing

Wrap Up on the Annapolis Boat Show 2026Oct 2026Whitecaps Sailing at the Annapolis Boat Show 2026Oct 2026Belize Sailing Vacations at the Annapolis Boat Show 2026Oct 2026Cruise Abaco at the Annapolis Boat Show 2026Oct 2026

From American Sailing — see the channel’s boat, crew, and every analyzed video.

The Sailing Directory Newsletter

One email with the fleet's best finds — the moments, boats, and stories worth your watch time. Enter your own address to get your own copy.