What to Do: Start your surf adventure at Ditch Plains, which has fast left- and right-breaking waves (lifeguards are there to keep an eye on you from 10 A.M. until 5 P.M. during the summer). The baked goods and breakfast burritos of Ditch Witch, a food truck in the beach parking lot, are justly famous and give you the requisite carbs for the next couple of hours. If you are in need of a refresher course, book a surf lesson through Air & Speed Board Shop. The teachers are patient and knowledgeable, although the front office's attitude can be indifferent (795 Montauk Hwy.; 631-668-0356; lessons, $100 including wet suit). Advanced surfers looking for more of a challenge and less of a crowd head to Camp Hero or Turtle Cove, both just below Montauk's iconic lighthouse and arguably the area's best breaks. When you are finished with your wave-riding day, join local geezers and tanned surfers exchanging battle stories at the bar at the Shagwong Tavern Restaurant. The food's nothing special, but the old-school atmosphere's great for a drink (774 Main St.; 631-668-3050). On a Friday or Saturday night, head to the Liar's Saloon for karaoke and cheap beer (408 W. Lake Dr.; 631-668-9597).

On your second day in town, join the crowd gathering for coffee and jelly croissants at the Montauk Bake Shoppe—the sugar fix will get you through another day of activity (Montauk Plaza; 631-668-2439). Rent some wheels at the Montauk Bike Shop (725A Montauk Hwy.; 631-668-8975) and set off for Montauk Point State Park, on the easternmost tip of Long Island. Trails will lead you to the lighthouse, built in 1796, with its fantastic views. You may even see seals sunning themselves on the rocks. Shoppers should dig for beachy vintage finds like Lilly Pulitzer dresses at Screaming Mimi's (662 Montauk Hwy.; 631-668-1631). At Tauk, you'll find everything from retro Tretorns to delicate jewelry and pretty housewares (54 S. Erie Ave.; 631-668-3686).

Where to Eat: Joni's has the best breakfast around—order the egg, avocado, and bacon wrap (9 S. Edison St.; 631-668-3663). On a sunny afternoon, Duryea's Lobster Deck is so good that people drive for an hour from other Hampton towns just for the melt-in-your-mouth lobster rolls, buckets of steamers, and whole lobsters, all in one of the prettiest settings in Montauk, on a wood deck overlooking the bay (65 Tuthill Rd.; 631-668-2410; entrées, $6–$33). It's BYOB, so stop in at White's Liquor beforehand and pick up a bottle of the Shinn Estate's 2005 Rosé, a rising star of North Fork Vineyards (771 Montauk Hwy.; 631-668-2426). Cheeseburgers and milk shakes are among the diner-style choices at John's Drive-In, with its 1960s-style booths and fabulous ice cream (695 Montauk Hwy.; 631-668-5515; entrées, $1–$9). If you are in search of a taste of the Hamptons scene, Nick and Toni's, in East Hampton, is Tinseltown transplanted to the East End, with Steven Spielberg and Gwyneth Paltrow among the patrons (136 N. Main St.; 631-324-3550; entrées, $22–$48).