1. Catch waves and live music in Montauk
120 miles, 3hrs by car or LIRR
Head East and don’t stop until you reach the tip of the Hamptons, where the ritzy clubs and high-fashioned vacationers give way to lifetime native fisherman and surfers who quit New York to chase the area’s big waves. If you’re hoping to hang ten yourself, spend your mornings at Ditch Plains, a beach where you'll be among many longboarders and have access to tasty seasonal food trucks. Afterward, spend your night dining over fresh seafood at 668 The Gig Shack, hit a Lynn's Hula Hut for some tiki drinks, and say goodbye to summer with live music as the sun sets behind a pond at the hip Surf Lodge.