5 SHELTER ISLAND
2 HOURS 30 MINUTES BY CAR
There’s no place better to while away hours by the sea than Shelter Island. Nestled between Long Island’s North and South Forks, it is separated from the competitive wealth and glamorous dissatisfaction of the Hamptons, and accessible only by a 15-minute ferry ride or by private boat. Although there are pockets of privilege, it’s low-key, even in season, when you can bake on Sunset Beach, cycle on quiet lanes or kayak up hidden inlets.
But when the wind whips up and icebergs spike the Long Island Sound, it is more special still. You can take bracing, salt-sprayed walks in the magical 2,100 acres of the Mashomack Preserve, skate on the frozen pond and hike or fly kites along empty shingle beaches.
For a peaceful place to stay, try the House on Chase Creek, or, for a touch of luxury, the Ram’s Head Inn, heading to the Shelter Island Heights Pharmacy – for eggs, bagels and overheard conversation. At the heart of this idyll lies Sylvester Manor, a house of mythic history and prettiness. Enter through the gates (open to the public Mon-Fri, 9-5) and you are in a magical world: the drive winds past gnarled trunks until the view opens to reveal a 17th-century yellow mansion so well-settled it appears to have grown there. If you come by the north ferry, leave by the south, stopping for lunch at Sag Harbour, and ending the weekend with a Bloody Bullshot and a long lunch in the old-world American Hotel.