You should post this in the Northeast forum for more/better responses. I had a lot of fun in Montauk last summer. Its all the way out at "the end" of LI though. If you hit any traffic, forget it!
The End I spent the summer out there in 08. Beautiful area, 60% open space with water everywhere. the waves are really nice, it holds swell pretty well and there are some great Longboard waves. If you happen to be surfing in the summer and especially on a weekend, it will be more crowded than any break you've surfed. LI runs west-east so there are a variety of exposures from almost due south to southeast. Oh yeah, traffic can be kinda bad too.
