Travel time: 1hr 50min
What to bring: The black card, sunscreen, and swim trunks
Best for: High rollers

Anybody who's a somebody in the Big Apple has partied in the Hamptons at one time or another. If you haven't yet, it may be time to reevaluate your life. Old money runs deep around these parts. A cluster of beyond wealthy enclaves at the eastern tip of Long Island, the Hamptons have a long history of attracting the highest of high rollers—from stockbrokers, to celebrities, and everyone else in between. Even Jay Z needs at least three weeks in the Hamptons. As for beaches, you can't go wrong with whichever you end up on. Still, if you're looking for the best in women and sunshine, hit up Coopers Beach in Southampton and/or Main Beach in East Hampton. If you're in the mood to party amongst the fishermen and surfers, head east to Montauk for some clams and waves.