Look up Northport Bay Long Island, that's the nearest official body of water, followed by Huntington Bay and then Long Island Sound. My brother just bought a house nearby and will have a boat too, so we can meet in the middle in Huntington Bay. It is a very nice boating area. When I was a bit younger and more daring I'd go out into LI Sound on nice days, but it can turn nasty fast and you can hit some big boat wakes out there.
I get what you mean about good healthcare, we are very lucky to have it here in the USA. As far as weather, we have hot summers, can occasionally have hurricanes (last big one was Sandy in 2012) and can have very cold winters with lots of snow, or mild with nearly none. When Sandy came I already had a generator, but the gas stations had no power so no one could get gas. Well I had 25 gallons stored up, went through that, then because we had pulled the boat out of the water, siphoned 40 more gallons out of it, to keep the generator going!
Here's a pic of me driving back with as many gas cans as I could buy about 4 hrs before the storm really got bad. The tide was not fully up yet but by nightfall that street was under water. Lucky we live on top of a hill!
