THE ADVENTURE: With consistent swells up to 10 feet, Ditch Plains Beach, just two miles from Montauk’s shop-lined main drag, is one of the top surf breaks in the east. Rent a longboard from Air and Speed Board Shop, rise at dawn, and hit the break before the wind picks up and the crowds arrive (board rentals, $40).
THE MEAL: Ditch Witch is a beachside food truck where surfers, locals, and urban refugees congregate for pastries, grilled sandwiches (try the turkey pesto), and breakfast burritos. The basic menu, scrawled on an old surfboard, belies the quality of the food. Even a cappuccino tastes better with a view of the surf. No phone or website (beautiful); east of town, Ditch Plains Road at Otis Road.