Where to Eat: In addition to the great hotel restaurants in Puerto Escondido, new hot spot Guadua has DJs and dishes like seared tuna with teriyaki sauce and shrimp rolls. The attached beach bar with hanging beds has become one of Puerto Escondido's happening spots (at Calle Tamaulipas; 52-954-107-9254; entrées, $5–$10). If the shacks along the beaches aren't your style, head instead to the restaurant of Mazunte's Posada del Arquitecto, overlooking Playa Rinconcito. Run by Italians, it has some of the best food on the coast (52-958-583-8982; entrées, $30–$73). La Crucecita's Onix, an airy, well-designed space where steak and grilled shrimp are among the best choices, overlooks the zocalo (603 Bugambilia; 52-958-587-0520; entrées, $10–$20). El Sabor de Oaxaca specializes in regional classics such as various moles (sauces) and chapulines—fried grasshoppers, which are actually quite tasty (206 Guamuchil; 52-958-587-0060; entrées, $6–$20).

And Don't Miss: Playa Cacaluta, just outside Huatulco, the pristine beach made famous in Y Tu Mamá También and now part of a national park, is a reminder of what this coast looked like when it was completely undeveloped. Be sure you come in that four-wheel drive.
–Ondine Cohane

Montauk, New York

Why: Tagged the anti-Hamptons by its champions, this former fishing village retains a more down-to-earth atmosphere than its famous neighbors to the west. Here the draw is funky 1960s motels, laid-back restaurants, and windswept ocean bluffs and beaches, plus excellent surf breaks at Ditch Plains that attract enthusiastic amateurs from all over the East Coast.

How to Get There: From New York City's Penn Station, take the three-hour train ride on the Long Island Rail Road to Montauk (with a change at Jamaica Station) for $21 during peak times and $15.25 off-peak (lirr.org). Alternatively, the Hampton Jitney leaves from Manhattan and Brooklyn—the bus also has a JFK and LaGuardia connection. Go midweek for lighter traffic, fewer annoying fellow passengers, and the $47 round-trip special for travel Tuesday through Thursday (hamptonjitney.com; round-trip, $51). If you want to explore farther afield, rent a car.

What You'll Need: Water temperatures can be quite chilly year-round, so pack a wet suit. For your adventures on land, casual clothes will do, but bring a dressy option in case you decide to venture to one of the ritzier towns, like East Hampton.

Where to Stay: Located right in Ditch Plains, the East Deck Motel books up way in advance—in addition to surfers, magazine editors and hipsters regularly set up camp here. They don't come for the amenities—this is definitely a no-frills establishment—but for the pleasure of being right on the water and for the camp reunion atmosphere (631-668-2334; eastdeckmotel.com; doubles, $190–$255). A short drive from town and only steps from the beach, the quiet, family-run four-room Sunrise Guest House comes with rockers on the porch overlooking the ocean (631-668-7286; sunrisebnb.com; doubles, $115–$295).