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Everyone knows that the Hamptons are the long time playground of the rich and famous – or those who used to be or hope to be. And the North Fork of Long Island has in recent years become a chic summer destination for those hoping to escape the madness of summer in the Hamptons. But now a new Hamptons-adjacent destination is on the radar of those in the know: Shelter Island. Our correspondent Meredith Lepore explains why relatively remote Shelter Island is the new luxury hot spot in the Hamptons, and shares tips on where to stay, dine and what to do if you decide to make this East End hideaway your next luxury vacation destination.

where is Shelter Island, and why is it such a hot luxury vacation destination in the Hamptons right now?

Though summer is quickly coming to an end, it is always fun to look back at what became the new must go-to luxury spot.

The hands down winner of summer 2022, at least on the East End, is Shelter Island. Somehow this small island that can only be reached by boat or seaplane makes the rest of the Hamptons look like Club Med. Shelter Island is known for its natural beauty – and for being markedly more low key than its flashier neighbors in the Hamptons.

Shelter Island is the new hot luxury vacation destination in the Hamptons, tips on where to stay, what to eat and do if you decide to visit.

Where to stay, what to do and eat on Shelter Island, the hot luxury vacation destination in the Hamptons.

Shelter Island has been rediscovered as a luxury vacation destination

So, was Shelter Island just discovered? Is that why it’s so desirable at the moment? Nah. This relatively remote island squarely situated between the North and South Forks of Long Island has been inhabited since at least 1620, when it was discovered by the British.

New hotels, inns and eateries open summer 2022

Although Shelter Island has always been known and loved by those truly in the know, thanks to a number of new openings, this summer turned out to be the moment when it came into the spotlight.

For example, The Pridwin Hotel & Cottages reopened this summer after a two-year renovation. As did the Ram’s Head Inn (which is said to give off a Dirty Dancing-resort vibe for all you film buffs).

The 150-year old Chequit Hotel has also reopened, featuring three new food-and-beverage concepts. The property once played host to Marilyn Monroe and Arthur Miller, as well as a dozen or so Kennedys. Now it awaits a new generation of celebs. Somehow this summer, it seems that everything on Shelter Island is very old, but somehow brand new. And therefore in very high demand.

the Pridwin Hotel & Cottages reopens on Shelter Island

“As a historic landmark on Shelter Island, we have sought to preserve the tradition of this exceptional property while enhancing offerings for year-round enjoyment,” Curtis Bashaw, managing partner of Cape Resorts which owns The Pridwin, told Travel & Leisure. “Being on 10 acres of waterfront property is pretty spectacular and part of the unique environment of Shelter Island is getting to explore the hidden beaches, bike paths, and hiking trails that are unlike any other place, certainly on the East End.”

The Pridwin, a waterfront property with a private beach, will still be going strong this fall.  The property will continue to offer family-friendly programming throughout the fall, including lawn games, arts and crafts, live music and kids cooking classes. Plus nature walks, hiking in Mashomack, farm tours at nearby l Sylvester Manor Farm, and yoga on the lawn.

Shelter Island can only be reached by ferry or seaplane

Of course, part of the mystique and aura of exclusivity that surrounds Shelter Island is due to the fact that you can’t just drive there. You’ll need a seaplane, or you’ll have to take the ferry.

This summer, Tailwind Air partnered with The Pridwin, as well as its sister property Baron’s Cove in Sag Harbor, to shuttle guests by seaplane from New York and Boston. The service runs from May through Thanksgiving weekend, weather permitting. At this time, both resorts offer guests the opportunity to book a la carte flights.

Where to stay and what to do and eat on a luxury vacation on Shelter Island in the Hamptons.

Where to stay and what to do and eat on a luxury vacation on Shelter Island in the Hamptons.

home prices on the upswing

With the three hotel overhauls, there has also been a surge in real estate prices. The island looks like it is out of a coffee table book so it is no wonder. According to Redfin, as of July of this year Shelter Island home prices were up 152.4% compared to last year, selling at a median price of $3.3 million.

But like all beautiful remote places comes the people that want to put it on the map. This can be both a positive and a negative. Will it lose its essence or its specialness when the influencers and the celebrities and the paparazzi come? Will it lose its unique identity and just become another East Hamptons town run over by “cidiots” as The New York Post asked this summer? There was even a Louis Vuitton popup this summer. 

Where to stay and what to do and eat on a luxury vacation on Shelter Island in the Hamptons.

The glamour is finding Shelter Island but perhaps it was always there and is just being discovered more now.  Here are a few more places you should check out if you manage to find yourself there soon.

What to do, eat and see when on Shelter Island in the Hamptons

1. where to stay: Sunset Beach Hotel

Perhaps the buzziest of all the hotels, inns and eateries on Shelter Island, Sunset Beach is a boutique hotel with just 20 ocean-view rooms and suites, owned by Mercer Hotel founder André Balazs.

Shelter Island in the Hamptons

Sunset Beach hotel on Shelter Island in the Hamptons. Photo Credit: Marty Lores.

It’s a go-to for the smart set – so dress accordingly. The people-watching is first-rate – and you can name-check photographer Gray Malin, who shot one of his iconic beach photos at Sunset Beach. Also adding to the appeal? You can literally walk off a seaplane and into the bar for a cocktail.

2. Marie Eiffel Market.

Step into a Nancy Meyers movie with this adorable market and restaurant by Marie Eiffel.

3. Léon 1909.

Another recent Shelter Island renovation, Léon 1909 is the site of a former bank that has been turned into a fine dining establishment. Valerie Mnuchin and her father Robert Mnuchin, the art dealer and banker, are the owners and hosts. The French and Italian restaurant strives to bring a bit of Europe to the island.

“During the early days of quarantine, we were spending so much time on Shelter Island and absolutely fell in love with it,” Munchin told Behind the Hedges. “The energy of the island reminded us of the Riviera and of the open fire, seaside experience at La Chaumière, a restaurant we love outside of Nice. We wanted to embody that spirit at Léon.”

4. Black Cat Books.

You’ll need a good book for the beach or when curling up in all those beautiful porch chairs. Try Black Cat Books, which moved from Sag Harbor 10 years ago. It has a strong selection of art, design and photography books.

5. Shelter Island Yacht Club.

This one may only be by invitation only, unless you are a member, but it would be an amazing invite to snag if you can pull it off. The Club was founded in 1876, and its in the National Sailing Hall of Fame.

Shelter Island is the Newest hot luxury vacation destination in the Hamptons

That’s our overview of Shelter Island, and what to do and see and where to stay, eat and drink if you go. What do you think, dear reader? Autumn escape sounding like a good idea right about now? Have fun.

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Meredith Lepore

Meredith Lepore is a travel and luxury writer and editor whose work has appeared in Travel + Leisure,, Marie Claire, Self and more. She’s visited many top hotels and restaurants (although she’s still waiting on that private jet ride, which she insists would help her get over her fear of flying.) Her personal definition of luxury is Doritos and The Gilmore Girls, plus the occasional meal at Per Se. Meredith resides in New York City with her Yorkie, Otis; her preferred home décor vibe channels Valley of the Dolls.