Peter Whinn

Pete Whinn does startup business stuff for a 9-5 grind, but spends evenings and weekends (and the occasional beautiful weekday afternoon, don’t tell his boss) teaching Learn to Sail and Advanced at the Boston Sailing Center. A Cape Cod native, he has a sailboat tattoo on his left arm representing his hometown of Brewster – you’ve seen the thing where you can use your arm to make the shape of Cape Cod – where he learned to sail at a young age. He has been teaching sailing to people aged 9-95 since his first job at 14 years old. He came back to Boston in 2015 after ten years of foolishly not living in New England and loves sharing his excitement for sailing with the BSC student community. 

Outside of Boston Harbor, he’s a frequent charterer and has captained trips on catamarans and monohulls out of Maine, Rhode Island, Florida, New York, and a bunch of Caribbean destinations. Ask him about getting into bareboat chartering via the BSC courses – it’s the best way to vacation! On the rare occasions in his free time when he’s not on a sailboat you can find him on a red motorcycle through Boston traffic or in a scenic area crashing his camera drone into the scenery. He lives in Roxbury with his boyfriend Dominick whom he taught how to sail, motorcycle, and ski and who in return tolerates his excessive number of hobbies. 

Meet

The Team

Instructor

Leo Gaskell

Leo has a life-long passion for sailing, and especially for helping other people to get the most out of the sport!

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General Manager

Dave Bryan

David joined the staff in 1988 as an instructor and after many seasons of running the instructional program he became the general manager of the BSC.

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Instructor

Jonathan Kannair

Joining BSC as a member in 1995, Jonathan immediately fell in love with sailing at BSC. He’s been crew and skipper during frostbite racing and Soling racing at BSC.

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Instructor

Martha Rand

Before coming to the Boston Sailing Center, she worked at the Southport Yacht Club in Maine where she would spend weekends racing her family’s J-27 or her pink and purple turnabout named Dazzle.

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