Shelter Island is a gorgeous place to escape to for a relaxing summer weekend out of the City. Here’s our complete low down on what to do and where to stay on Shelter Island this summer.
THE RAM’S HEAD INN – a throw back to the island’s hey day. This ye olde hotel is incredibly charming. Rooms have no tv and lovely simple white linens and antique furniture. We find the old-fashioned charm endearing and it’s certainly far from the maddening crowds of Sunset Beach on a summer weekend.
THE CHEQUIT INN. Built at the end of the 1800s, this inn is in the historic Shelter Island Heights district and has a very old-fashioned air to it, totally befitting of the island. Simple, antique filled rooms makes this a darling little spot, right in the middle of the bustling harbor area.
SUNSET BEACH Hotel. The hippest hotel on the island. Click here to read the post
LA MAISON BLANCHE. A chic, French inspired country inn. Click here to read the post
WHAT TO DO
COCKTAILS AT THE RAM’S HEAD INN
We love to go to the Ram’s Head Inn for sunset cocktails. An old-fashioned island institution, we always head here around 5pm, grab an adirondack chair on the hill, order a glass of champagne and watch the sunset over the water.
On the drive over to the Rams Head, you pass through the historic Dering Harbor area filled with white gin palaces built in a very different time. They make us think of the Great Gatsby and we always make a detour to look at these perfectly preserved houses.
The entire island is so green and lush, it feels like you are in the middle of the country side, not an island in the Hamptons. Terrific for a scenic drive or a leisurely bike ride through the quiet country roads.
Shelter Island is a fantastic spot to go kayaking. Because it is situated between the North and South Fork of Long Island, the water is very calm. Hire a Kayak at Shelter Island Kayak Tours and set off to explore the island’s many harbors, creeks and vast, calm shoreline.
Mashomack Preserve in the middle of the island spans over 2,100 acres. It covers over a third of Shelter Island and was taken over by the Nature Conservancy in 1980 as a way of protecting this perfect peninsula on the island. It’s a great place to hike and truly get lost in nature.
WHERE TO EAT
Vine Street Cafe is the fanciest restaurant on the island. People jump the ferry from the Hamptons to eat at this swish joint. They serve seasonal dishes prepared with local organic ingredients in a clever and inspired way. Make sure to book ahead, as this place is quite the hot spot, it gets booked up weeks in advance.
Sunset Beach & La Maison Blanche also have lovely restaurants. Check out the links above for further information.
Reddings Market is a family owned food emporium perfect for picking up a picnic for your Shelter Island excursion or day at the beach. A great one stop shop for a snack or a casual lunch in a wonderful spot, right on the harbor.