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.
Where To Stay
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.
Where To Stay
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.
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