Montauk
New York
Surfer bros and biddies will want to hop straight on the Jitney or LIRR on a Friday afternoon to head out to Long Island's easternmost point. Known for its chill surfer vibes (despite recently attracting swells of cool-kid crowds), beach bars and gnarly waves, Montauk is a summer paradise for those in need of a good break. Hit the water first thing Saturday morning and then beat the crowds to Gurney's or Surf Lodge for a well-deserved bottle of rosé.