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There are a bunch of sailboat charter places on the CT shore. Suggest you google: 'sailboat charters in Connecticut'.
Also, Oyster Bay has some sailboat rentals and charters.
Any of the islands out there are destinations for sailors in the season (Block, Cuttyhunk etc.) as is the Peconic Bay area.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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