From the tony South Fork to its rustic northerly counterpart, Long Island is both a playpen for the well-to-do and a calming, cozy respite.
Author Sarah Horne
DAY ONE | Awake in a cloud of exuberantly preppy Ralph Lauren sheets in a graceful four-poster bed at the 1708 House (1), an old-fashioned B&B on Southampton’s Main Street. At breakfast, in the antiques-crammed formal dining room, you remember your posture and steel yourself for a day among the Social Register set.
Stepping out into the sunshine on Main Street, you take in the trapped-in-time village. At a distance, with its church steeple peeking through the trees, genteel Southampton could be any well-preserved town in America. But the yellow Lamborghini careering around the corner gives you a hint that all is not quite as it seems.
You pop into BookHampton (2), where the local gentry pick up their highbrow poolside reading, then check out Hildreth’s Department Store (3), a rambling relic that’s been in business here since 1842. Forget penny candy—this is where young wives have bought their scallop-edged throw pillows and rattan porch furnishings for generations.
Next, stop in the Parrish Art Museum (4), a 19th century gallery with an impressive collection of paintings by the likes of Willem de Kooning, Roy Lichtenstein and Chuck Close, before perusing Jobs Lane’s (5) various shrines to resort wear. At Vilebrequin, you check out the baby blue swim trunks dotted with Adirondack chairs; at Harmont & Blaine, it’s corduroy pants in magenta or jade. Finally Stubbs & Wootton lures you in with a pair of velvet slippers. At the register you ponder yacht names. What has come over you?
In your new duds, you stand a bit taller as you swan into Silver’s (6) to lunch (it’s a verb here) and watch Manhattan’s business elite twitching under the handwritten “No cell phones” sign. You order the house specialty, a mammoth $17 BLT like none you’ve ever tasted: thick slabs of warm Eli’s Tuscan bread, rashers of smoky bacon and a generous slathering of mayo. Your cardiologist might be alarmed, but not to worry: You’re about to offset the meal with a hearty walk.
Hop in your Jaguar XK convertible and drive through the village’s Estate Section (privet hedge–lined streets packed with nine-bedroom “cottages”) before you find Gin Lane and the beach. Park near St. Andrew’s Dune Church (7), an old life-saving station turned seaside chapel, and doff your shoes before climbing up the slope to Cooper’s Beach (8). Walk east until the sunbathers thin out and it’s just you and the locals in their rolled-up khakis, letting their Labradors stretch their legs. Then find a spot in the dunes to take in the gnashing Atlantic.
After walking until your calves begin to protest, you drive around Lake Agawam to Meadow Lane, top down, listening to the firm pop of the tennis balls at the prestigious Meadow Club (9) and peeking at the slivers of vast houses down ominously long private driveways.
Then it’s back to your lodgings for a quick snooze before you freshen up for dinner at Red/Bar Brasserie (10), a Mediterranean eatery in a sprawling farmhouse that served as a speakeasy during Prohibition. In honor of the repeal, sidle up to the bar before positioning yourself at a corner table to watch the jovial crowd while you dine on Malpeque oysters and black truffle–stuffed chicken breast. It’s good to be king.