Once a haven for serious surfers and scruffy fisherman, Montauk today is a Hamptons-like destination for those looking for less stuffiness and chill vibes. Getting out there takes some commitment since it's in the eastern-most part of the state. There is traffic - and lots of it - before you reach the town line. On peak summer weekends it can take up to four hours from NYC suburbs.
The 17-square-mile town is bordered by the Atlantic and Block Island Sound. If you are looking for a quieter visit head to "the End," as locals call it, in the fall. If you are okay with crowds brave the swell of summer visitors to escape from the city and see boats on the sparkling ocean.
If you are an avid surfer don't miss Ditch Plains, with legendary breaks and jagged cliffs. Or hang ten with beginners lessons on one of the beach-front schools.
What will your Montauk story be?