Give Me Shelter

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



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.


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.


If you can’t handle the car journey, you can always hop on Andre Balazs’ seaplane, Stnd Air and be on the Island in 45 minutes from Manhattan.
If you want a simpler life, you can catch the Long Island Rail Road all the way to Greenport. The station is about 100 yards from the Shelter Island Ferry.  Catch the ferry as a foot passenger, or even better still, bring your bike on the train and then ride around the island all weekend.
The Rams Head Inn. 108 Ram Island Drive. Shelter Island. New York. 11965. Tel: 631 741 0811
The Chequit Inn. 23 Grand Avenue. Shelter Island Heights. New York. 11965.  Tel: 631 749 0018
La Maison Blanche Hotel. 11 Sterns Point Road. Shelter Island, New York. 11965. Tel. 631 749 1633
Shelter Island Kayak Tours
Mashomack Preserve
Vine Street Cafe. 41 South Ferry Road. Shelter Island, New York. 11965. Tel: 631 749 3210
Reddings Market. 184 North Ferry Road. Shelter Island, New York. 11965. Tel: 631 749 0003 
Long Island Rail Road
Shelter Island North Ferry

Sunset Beach

IMG_0357Shelter Island is much closer to Manhattan that we realize.  Yesterday on a whim, we decided to head down there for lunch.  It took only an hour and a half from the City to the ferry at Greenport, then a relaxing five minute boat ride to the island.

We adore Shelter Island.  Nestled between the North and South Fork of Long Island, it’s remained untouched by all the development that has exploded throughout the Hamptons over the years and still feels like a sleepy and idyllic island get away.


The first and only hip hotel on the island, Sunset Beach is part of the empire of hotelier Andre Balazs, which includes the famous Chateau Marmont in West Hollywood, The Standard Hotels and The Mercer Hotel in Soho.  We sometimes wonder if he opened this place so he’d have somewhere to go for a good glass of rosé near his own Shelter Island weekend house.

The hotel manages to make you feel like you’re somewhere between the South of France and St Barths. Beautiful, well travelled staff serve French inspired salads and rosé  to a discerning Hamptons crowd who zooms over on the ferry to hang out in what might be the chicest place in all of the Hamptons. The open air restaurant looks at the beach across the road, which lends the place a French Caribbean feeling.  That and the cooler than cool African and French music they play from the upstairs open air bar, just makes you want to pull up a stool and stay here all day.

Look closely and you’ll see that the cafe and restaurant walls have wonderful photo collages of some of the fun that’s been had at Sunset Beach over the years as well as beach scenes with the likes of Bridget Bardot in the South of France.  These photos are really the essence of the place.

The hotel rooms are simple but stylish and functional and the location on the island can’t be beat.  Right across from  a gorgeous mellow sandy beach, wonderful for both swimming laps, kayaking and paddle boarding.  There’s a pétanque court, table tennis and fire pit too, so there’s very little reason to leave the compound.

They have their own cute little boutique at the hotel and it’s the only spot on the island to get a fashion fix.  One of the many reasons we love Shelter Island, as it’s not about shopping but, if like us, you sometimes desperately need a new pair of the latest sunglasses, an Isabel Marant summer dress, a Balinese sarong, a copy of the Paris Review to read and a Jonathan Adler candle (another island inhabitant), then the boutique has what you’re looking for.

As the summer gets in to full swing, the restaurant and bar get pretty crowded, so if you’re heading here for a meal, it pays to call ahead and book.  Our favorite time to stay is mid-week.  It’s charming and you get to experience the beauty of the island with just the locals.

Sunset Beach Hotel. 35 Shore Road. Shelter Island. New York. 11965. Tel: 631 749 2001