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I am on eastern Long Island on the North Fork. Not sure if I would attempt that in a 17 footer. When I was younger (16) I brought my father's Sea Ray 280 Sundancer from Hempstead Harbor to Montauk. It can get kind of rough out there in Gardiner's Bay. I was just there last weekend.

If you do give it a shot I would come around Orient Point through the Plum Gut and then come west to Shelter Island. Cross Gardiner's Bay close to Shelter Island, head south to the South Fork, then east to Montauk. You could even stop in Greenport for fuel and food, and then head across to Lake Montauk.