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Amy, go down to North Cove (the marina at the World Financial Center) and look for the Manhattan Sailing Club. They'll give you a tour and probably a ride and who knows, you might decide to join.
I think they also have some boats up at the chelsea piers, and if you take the PATH train over to NJ there's the Newport Sailing School & Cruising Club right across the river as well, 1-201-626-3210.
Great places to learn and get a lot of sailing for your buck without having to go to the outer boros.
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