Originally Posted by KindOfBlue
Look up a restaurant called "Sunset Saloon" in Montauk. It's in the bay west of Montauk lake called Fort Pond Bay. I have anchored in there and pulled the dinghy up on the beach while I had dinner. I haven't been in 2 years, but I had a great time and the sunset is amazing.
They've gone through a couple name changes in the last few years. Not sure of the current name. Also they've gone upscale a bit. Still a very good bet for a great time.
Watch the wind direction there in Fort Pond Bay. It's very exposed to any winds with a north component. And it's very deep, right off the beach. It goes to 60 feet fast. Actually it was the site of torpoedo testing during WW2. Something about it being the 3rd deepest bay/harbor/something in the world.
Also watch for very high density of lobster pots/floats. I would advise against going in or out at night.
Historical note: that was the original site of the town of Montauk. Hence the train station nearby. The hurricane back in the 1930s wiped it out. A friend's family's (grandmother's) cottage was found floating, dragged back and repositioned on much higher ground.