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Insider's Guide to the Hamptons

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Photo: Theo Morrison

On my first visit to the Hamptons some 20 years ago, I stayed with friends at a sprawling rental in Southampton. We hired a now-defunct taxi service (Mercedes-Benzes, of course) to take us to overpriced restaurants and red-rope clubs. It was exactly how I’d pictured Long Island’s South Fork—a bit pretentious for my tastes.

But there was something about this beachy New York destination that spoke to me: the dramatic dunes; the shingled windmills; and that famous light that has attracted artists as varied as Jackson Pollock and Winslow Homer. So I kept coming back, renting houses with friends and staying at inns from Amagansett to Sag Harbor, East Hampton to Montauk. Eventually, I bought a cottage in Amagansett with my husband (whom I met at a bonfire on Atlantic Beach).

Over the years, I’ve discovered a very different side to this coastal getaway. My Hamptons is all about low-key seafood shacks, quirky antiques shops, and placid bays that are perfect for beachcombing. Sure, you might run into Paul McCartney at the local café or spot Gwyneth Paltrow’s kids selling lemonade at a makeshift stand—but that is just evidence of the Hamptons’ many faces.

Read on for my highly selective guide.

Where to Stay

The Classics

The Maidstone Arms, a sprawling Greek Revival inn overlooking the town pond, has been the place to stay in East Hampton for generations. A much-welcome overhaul gave it an offbeat new name, c/o The Maidstone, and a Swedish design sensibility; most of the 16 rooms and three cottages are inspired by famous Scandinavians (Arne Jacobsen, Hans Christian Andersen, even Edvard Munch). Just down the street behind an ivy-covered façade is the Baker House 1650, with five Arts and Crafts–style rooms and two lovely outdoor pools. Another updated classic is the Inn at Quogue, in an 1824 farmhouse. The rooms now have a suitably beachy, if slightly cookie-cutter, feel. The American Hotel, a red-brick Victorian in the center of Sag Harbor, stands in stark contrast: it hasn’t changed much since 1846. And that’s just how guests like it, with its faded elegance, backgammon tables in the lobby, and a bartender who will soon know your name. Another popular dowager: Southampton’s 152-year-old A Butler’s Manor, which is surrounded by lush English gardens. Each of the five individually decorated rooms is named after an estate where co-owner Christopher Allen—a former butler—once worked.

The New Guard

By far the most luxurious hotel in the area is Amagansett’s Inn at Windmill Lane, briefly known as the Reform Club (rumor has it the owners changed the name because it sounded like a rehab center). It is worth the splurge: the seven suites have wood-burning fireplaces; each of the three cottages also has its own gym and steam room. In Montauk, Ruschmeyer’s is a summer camp for grown-ups. Think cabins clustered around a decorative tepee, bingo nights, Ping-Pong, and a bar in an oversize sandbox. Solé East Resort is set in a Tudor-style house, with 61 whitewashed rooms; an allée of bamboo leads to eight garden cabanas out back. On Shelter Island, La Maison Blanche, named after a hotel in St.-Tropez, channels the south of France: pétanque courts, a Gallic brasserie, and an authentic boulangerie.

Waterfront Hotels

There are surprisingly few good hotels on the water in the Hamptons, but the rooms are clean and simple at Amagansett’s White Sands Resort Hotel, smack on a spectacular Atlantic beach. Worth booking for the ocean views alone is Montauk’s hillside Panoramic View Resort & Residences; the pastel bathrooms and kitchenettes betray its previous life as a 1950’s motel. On a small islet, the Montauk Yacht Club Resort & Marina has a scaled-down replica of the town’s famous lighthouse, not to mention three pools, four tennis courts, a spa, and a marina. For a dose of glamour by the sea, check out Shelter Island’s Sunset Beach, which has a vibrant social scene, its own brand of rosé, and spectacular sunsets (as the name would suggest). Last summer, owner André Balazs introduced StndAir, a bright red seaplane from Manhattan to East Hampton that sometimes lands in the cove in front of the hotel. One-way rates start at a very democratic $99—though those seats go fast.

Where to Eat

The Hot Dish

The East End is buzzing with anticipation over chef Tom Colicchio’s long-awaited Topping Rose House, set to open late this season in an 1800’s Bridgehampton mansion. (There will also be an adjoining hotel, designed by Alexandra Champalimaud of Hotel Bel-Air fame.) Where to eat in the meantime? Foodies flock to Shelter Island’s Vine Street Café for crisp calamari salad and miso salmon in a simple space with high, beamed ceilings. There’s a trio of gourmet finds hidden away in the tiny town of Water Mill: Robert’s, which serves meticulously prepared Italian cuisine in a 1670 stagecoach house; Mirko’s, run by a husband-and-wife team (she works the room while he’s in the kitchen making his famous Croatian stuffed cabbage); and Dish, a BYOB restaurant with only 16 seats (a charming touch: several days out, the owner confirms your reservation by e-mail and sends along the evening’s prix fixe menu). It’s no surprise that Gabby Karan De Felice’s Tutto Il Giorno is so stylish, considering her mother is Donna Karan; the lusty dishes range from branzino al forno to house-made pappardelle. The restaurant has two locations: Sag Harbor (the original) and Southampton. In Montauk, two places are adding to the town’s new culinary cred: Navy Beach, a former surfer’s bar right on the sand with a great menu of ceviches, and the waterfront Crow’s Nest, a rustic-chic spot from hipster hotelier Sean MacPherson.

Farm (and Ocean) to Table

Despite all the changes, the South Fork is still home to fishermen who make a living offshore and family farms that have been around for generations—providing ample resources for chefs such as Joe Isidori at Bridgehampton’s Southfork Kitchen. He has gained a following for his unswerving commitment to sustainable seafood, fresh produce, and Long Island wines. The most coveted reservation continues to be East Hampton’s 24-year-old Nick & Toni’s, which is a who’s who: Howard Stern, Lou Reed, and Naomi Watts, just to name a few. Chef Joseph Realmuto sources from the best local purveyors for such dishes as dandelion greens and pork-belly croutons in a white-anchovy vinaigrette. In Montauk, Jennifer Meadows, the adorable chef-owner of Fishbar, is so friendly with the fishermen that she radios them when they’re at sea to check out what they’ve caught. This summer, she’s opening Bliss Kitchen, an eclectic takeaway with a fleet of taco-delivery bikes buzzing around town. One of the toughest tables to get in Montauk is at Dave’s Grill. In-the-know diners start dialing at 4:15 p.m.—when the reservation line opens—to sample hearty cioppino and onion-and-potato-crusted flounder.

Seafood Shacks

There’s nothing like a platter of good old fried oysters or steamers by the sea. At Canal Café, tucked into a Hampton Bays marina, you’ll get one of the most generous lobster rolls around—plus great water views and salty air in your hair. In a weathered cottage on Sag Harbor’s wharf, groupies line up at the Dock House for the clam chowder and steamed lobsters; the live specimens are kept in an antique bathtub next to the front door. You can’t get a better endorsement than chef Bobby Flay, who has been spotted at Bostwick’s Chowder House, East Hampton’s destination for shoreside favorites. On the stretch between Montauk and Amagansett, look for the yellow-and-white-striped umbrellas: the open-air Clam Bar serves simple seafood (I prefer it to the more famous Lunch, a.k.a. the Lobster Roll, down the street). Bring a bottle of rosé to Duryea’s Lobster Deck, set on a rocky Montauk outcropping and renowned for its well-priced lobster. Just be prepared for a long wait.

Best Breakfasts

Almost as social as dinner, breakfast is an institution in these parts. So local residents were devastated when the decades-old Fairway Restaurant, at Sagaponack’s Poxabogue Golf Center, lost its lease in 2010. After a heated battle with the town, it soon reopened, looking as retro as ever and once again supplying happy Hamptonites with no-fuss bacon and eggs. Another unassuming cult spot in a 1959 Hampton Bays motel is the Hampton Maid, known for its fluffy omelettes and decadent French toast. A few notches up on the culinary barometer is Estia’s Little Kitchen, a modern-Mexican roadhouse in Bridgehampton where regular Alec Baldwin has a menu item named after him: the egg-white “Big Al’s Burrito.” In Amagansett, the cheddar-scallion scones alone are worth the wait at Mary’s Marvelous, a low-key neighborhood haunt that also makes addictive cookies and sweets. You’ll also encounter lines outside Montauk’s Mr. John’s Pancake House for such indulgent combinations as the “ET” (chocolate and peanut-butter chips) and the “sabre” (coconut-filled and topped with coconut syrup). On a health kick? Follow the surf crowd to Joni’s for whole-wheat breakfast burritos and chai lattes.

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