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IMHO the best way to learn is to just do it with a small centerboard sloop (something like a Vanguard 420 comes to mind...) on any body of water bigger than 200 acres.
There are a number of opportunities for sailing instruction on the Chesapeake I would think but sounds like you are too far away to enjoy the environs.(?) How far are you from Lake Moomaw (just sou'west of Lexington)? Great "little" lake, some breezes though the mountains make 'em flukey.
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