Captain Bios

Our Captains

Sailing schools are about sailing instruction and the best sailing schools have the best sailing instruction. That’s why from Lake Erie to the Virgin Islands and back to Lake St. Clair, Fair Wind Sailing School strives to find and develop the best possible sailing instructors. Fair Wind Sailing School believes the best sailing instructors possess a combination of outstanding sailing experience, unbridled enthusiasm for sailing and a strong desire to help new sailors learn how to sail. With 6 Instructor of The Year Winners, 4 in Just the Past 2 Years our track record speaks for itself. Moreover, if want to learn from an award winning instructor in the Caribbean or Lake Erie, Fair Wind is your only option, because we have them all!!

Captain Dave

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Captain Dave is the founder of Fair Wind Sailing School and teaches at all Fair Wind locations. Captain Dave is an Instructor of The Year Award Winner. He holds a U.S. Coast Guard 100-ton Master License and is certified to teach all courses through Celestial Navigation and Ocean Passage.

Captain Francis

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Captain Francis hails from Massachusetts. He teaches for Fair Wind in the Virgin Islands, Chesapeake Bay and Bahamas. He is certified to teach through Advanced Sailing and is an Instructor of The Year Winner . Capt. Francis is a passionate about sailing and has taught for over 10 years. He is certified to teach ICSO, US Sailing and ASA classes.

Captain Gary

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Captain Gary hails from Ohio and teaches for Fair Wind Sailing School in the Virgin Islands and Great Lakes. He is a past winner of the Instructor of The Year Award .;Capt Gary is the proud owner of a beautiful ketch which he berths on St Thomas. He is FWSS's longest tenured instructor and is certified to teach ICSO, US Sailing and ASA classes.

Captain Eric

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Capt Eric teaches all Fair Wind classes in the Bahamas aboard his beautiful Morgan, Out Island 41 Dream Ketcher. He has salied fo more than 30 years and covered more than 13,000 miles in teh Abacos, Mediterranean, Caribbean and Atlantic. A Canadian citizan, he is fluent in both French and English. Capt. Eric is certified to teach both ICSO courses (through Bareboat Charter) and Canadian yachting Assoc. (CYA) classes.

Captain Keith

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Captain Keith teaches for Fair Wind Sailing School on the Chesapeake Bay. He is the founder of Upper Bay Sailing School and a past winner of the Instructor of The Year Award . Captain Keith has extensive sailing experience throughout the Chesapeake Bay, Virgin Islands and US East Coast and has completed 12 passages between the Caribbean and the Chesapeake Bay.

Captain Ethan

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Captain Ethan teaches for Fair Wind Sailing in the Caribbean since 2010.

Captain Thomas

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Captain Thomas Hamilton teaches for fair Wind Sailing for 5 years in both the Caribbean and Chesapeake Bay. Capt Tom is one of our most experienced instructors and has a detailed knowledge of both locations and FWSS yachts. He has successfully completed several open water passages between teh US East Coast, Bermuda and the Caribbean. Capt Tom is certified to teach both ICSO and ASA classes.

Fair Wind Sailing