Escaping the Hamptons may seem silly, but maybe you have your reasons - or maybe you need a reason. Shelter Island has a perfect one.
The alfresco dining patio of Red Maple at The Chequit inn on Shelter Island.
Hop on the Shelter Island Ferry from Sag Harbor and make a beeline for The Chequit. This former religious retreat turned high-society destination—once visited by Marilyn Monroe and Frank Sinatra—has been redone to the nines, all pale pinks and grays with Navajo touches, rattan and slate, reclaimed floors, Turkish towels, and straw hats, not to mention killer views of the harbor.
We suggest shacking up in the Terrace Suite with its adorable lounge swings and string lights—but every room is just right.
A deluxe king room in pale pinks and grays.
A cold brew at The White Hill, the coffee shop downstairs, is a must, along with one of its picnics to go. Take a stroll and peek into the beautiful Victorian homes, or explore the quiet beaches, or have some serious boat envy in Deering Harbor. Or don’t. Hole up on The Chequit’s wraparound porch for the fabulous cocktail hour, surrounded by lanterns, throw rugs, and rockers.
In the evening, grab an outdoor seat at the inn’s Red Maple restaurant, with everything made for sharing. We recommend cornmeal calamari, local fish with Sylvester Manor veggies, and a couple of flatbreads for good measure. At this point, you may be too relaxed to consider dessert on Sunset Beach, but consider it anyway. You’re on vacation from your vacation, after all. The Chequit, 23 Grand Ave., Shelter Island, 631-749-0018; thechequit.com