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 THREE | Open your eyes in your serene, white-on-gray room, relishing the priceless luxury of silence before you grudgingly pack your bags, take breakfast on the patio downstairs and hop in the car to make your way to Sag Harbor. Peek into Sylvester & Co. (1), the modern general store on Main Street, for a glimpse at decor that will look just as good in your pied-à-terre or suburban bungalow as it will in your beach house. Next stop is The Sag Harbor Whaling Museum (2), housed in a 19th century mansion that’s now part Masonic temple, part mariners’ time capsule. See whaling ship captains’ licenses signed by the likes of George Washington and Andrew Johnson juxtaposed with intricately carved bones and dastardly-looking spears. Portraits of prominent, long-dead townsfolk glare down at you indignantly as if to say, “Flip-flops? Really?”
Walk down to the harbor, scanning for megayachts and pleasure craft disguised as lobster boats (codesigned by Billy Joel), before heading to The American Hotel (3) for lunch on the porch. If so inclined, toast your final moments on the South Fork with a glass of chardonnay from the Wolffer Estate Vineyards in nearby Sagaponack and some Gardiners Bay oysters.
Seeking a more rustic setting, you head to the Shelter Island (4) car ferry and buy a oneway ticket. After the short trip across the bay in the breezy summer heat, you wind your Jag through the backroads of Shelter Island, where battered Volvos rule the road. For a complete retreat make your way to Ram Island, across a narrow causeway, and do some beach combing. In this secluded spot, it’s almost impossible to believe that the glitzy madness of the Hamptons is just a stone’s throw away.
Continue your adventure by taking the North Ferry to Greenport (5) on the North Fork. You sense that you’re discovering an unspoiled, lovely little town as you wander Front Street, peeking into the window of the Coronet (6), a throwback diner that’s little changed since the 1940s. Take a detour to the miniscule hamlet of Orient (population: 709) for a real sense of how unchanged life on the North Fork can be. Flags flit langorously on the porches of whitewashed houses, while three old-timers sit about watching the game in the general store, impervious to your presence.
As the afternoon light begins to deepen, you head to the North Fork Table & Inn (7), your home for the night, and settle in for an evening in locavore heaven, thanks to the fertile farmlands of the area.
Around you, elegant city dwellers and locals alike gather around the white linen–covered tables. There’s a happy, casual din as you tuck into your succulent orange-glazed Berkshire pork loin. Like Goldilocks, you think, you’ve gorged on the glamour of the South Fork, tasted the solitude of Shelter Island and have finally gotten it just right.
SARAH HORNE is never coy about her ritziness.