Montauk, New York

If you start in New York City and head east, the very last spot you’ll hit before barreling into the Atlantic Ocean is Montauk, NY. With all the breezy style of the Hamptons, Montauk also happens to be one of the premiere surfing spots on the Eastern Seaboard. The best breaks are on Ditch Plains Beach, and if you’re thinking you might need a refresher on your surfing skills (or a first lesson), call up the East End Surf School. After hanging ten, head to Gosman’s Dock for a cup of chowder and a lobster roll.