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Style

Revamped Victorian inn

Setting

Slow-mo Shelter Island

The Chequit is a restored 19th-century clapboard-clad inn, set in a serene harbourside hamlet on Shelter Island. The rooms are subtly styled in pastel pink and grey, with Native American patterned rugs on the floor and Turkish towels hanging from rustic ladders next to the claw-foot bath tubs. The vintage-print veranda daybeds are all set for a snooze, but don’t forget to explore the island too; there are clearwater coves for kayaking, nature trails for hiking and country lanes for biking. A wholesome breakfast is included, and in the evenings signature cocktails flow at the bar and dinner is served around the wise old maple tree in the garden.

Smith Extra

Get this when you book through us:

A bottle of wine in your room, or over dinner at Red Maple

Facilities

Photos The Chequit facilities

Need to know

Rooms

36, including 6 suites.

Check–Out

11am. Earliest check-in, 4pm, but flexible, subject to availability.

Also

The building dates back to 1872, and was converted from a Methodist community hall into a hotel in 1874. In its 1960s heyday, the likes of Marilyn Monroe and the Kennedy family stayed here, but it later fell into a state that was a bit… err… shabby-without-the-chic. David Bowd and Kevin O’Shea (head honchos of the Salt Hotels minigroup) came to the rescue in 2014. They restored the building to the lofty standards of their Provincetown boutique hotels – Salt House Inn and Eben House – and they’ve since repeated the trick at The Asbury in New Jersey.

Hotel closed

Annually on Thanksgiving and Christmas days. From November 2017 to March 2018, the hotel will only be open on Fridays and Saturdays.

At the hotel

Café, car park. In rooms: Free WiFi, air-conditioning, minibar, free bottled water, C.O. Bigelow bath products.

Our favourite rooms

The Garden Suite boasts two bathrooms and is flooded with light from its large bay window; outside, it has a private terrace with a table and sofa built for two. The bedroom in the Loft has a claw-foot bath tub under its vaulted ceiling, almost splashing distance from the king-size bed.

Packing tips

Boots and binoculars if hiking in the Mashomack Preserve is your bag. If not, a straw sunhat and a good book – John Steinbeck lived across the water at Sag Harbor, and his Travels with Charley begins with a trip to Shelter Island.

Also

The hotel’s White Hill Café has you covered for stir-brew coffee, sweet treats from Brooklyn-based Baked, and grab-and-go picnics for the beach.

Children

All ages are welcome. Most rooms have space for a travel cot, but it’s best to check when you book. Highchairs are available in the restaurant.

Food and Drink

Photos The Chequit food and drink

Top Table

On sunny summer days, there’s no beating a table under the maple tree on the front lawn.

Dress Code

Anything at ease, and that includes shorts, t-shirts and those shoes you only really wear on holiday.

Hotel restaurant

The dinner and Sunday brunch menus at Red Maple feature American favourites expertly crafted by chef Gayle Scarberry using seasonal local produce. There’s market-fresh fish every day, and the Red Maple burger is the signature pick for carnivores. Veggies are well-looked-after too, with homestyle mac ‘n’ cheese and portobello mushroom with quinoa and goats’ cheese. Brunch is wholesome and hearty – think syrup-soaked pancakes and fillet-steak eggs Benedict. Inside, the restaurant has dark-wood floorboards, statement wallpaper and vintage furniture. Out on the lawn, tables and chairs are clustered around the mighty maple tree, and light bulbs are strung between old-world lamp posts. 

 

Hotel bar

The Red Maple bar shakes up its own takes on classic cocktails; try the punchy Ginger Cosmopolitan or Red Maple Margarita. The reception desk moonlights as the Lobby Bar each evening, serving a selection of wines by the glass and bottle. 

Last orders

Breakfast is from 8am until 10.30am. Red Maple is open for dinner and drinks from 5pm to 10pm; brunch is on Sundays only, from 10am to 3pm. The Lobby Bar serves drinks from 4pm until 9pm.

Room service

For breakfast-in-bed, just ask.

Location

Photos The Chequit location
Address
The Chequit
23 Grand Ave
Shelter Island Heights
11965
Shelter Island Heights
United States

Planes

New York’s JFK airport is the largest international hub, and it’s actually on Long Island, between the city and the Chequit – it takes just under an hour to drive from the airport to the hotel. Many major airlines also fly into LaGuardia airport (also on Long Island) and Newark airport, which is on the other side of the city.

Trains

From New York, take the Long Island Railroad from Penn Station to Greenport (the journey takes two and a half hours), then cross the street and hop on the North Ferry to Shelter Island. If you’re coming straight from JFK, all trains stop at Jamaica station, next to the airport.

Automobiles

If you plan on exploring Shelter Island and the Hamptons nearby, a car will come in handy. The area is well-connected to New York (a three-hour drive away), and the ferries to Shelter Island take cars as well as foot passengers. The best deals on car hire are usually at New York’s airports, rather than in the city. The Chequit has its own car park, which is free to use during your stay.

Other

The little boat trip is part of the charm on any trip to Shelter Island. There are two crossings, each taking just a few minutes: the North Ferry from Greenport docks just down the hill from the Chequit, while the South Ferry links the other side of the island with the Hamptons. For longer-distance roadtrippers headed north to Boston and beyond, there’s the nifty Cross Sound Ferry from nearby Orient Point to New London in Connecticut, which cuts out the drive back down Long Island.

Worth getting out of bed for

The best of the beaches are: Hay Beach for sweeping views of Gardiners Bay and Bug Light Lighthouse; Shell Beach for activities including kite-surfing and paddleboarding; Crescent Beach for pink-tinged sunsets and an excuse for cocktails at Smith-approved Sunset Beach hotel. Stop by Picozzi’s bike shop and pick up a two-wheeler for a day of island-exploring; the roads are almost all yours and energy-sapping hills are mercifully few and far between. Or, ask the hotel to book you an activity nearby: golf, fishing, sailing and kayaking are some of the most popular. Mashomack Preserve nature reserve draws hikers, bumpkins and birdwatchers to its wetland trails. Check the concert schedule at the Perlman Music Program, an academy for string musicians run by renowned violinist Itzhak Perlman. The Hamptons are just over the water on Long Island; Sag Harbor, Southampton and East Hampton are the places to see and be seen.

 

Local restaurants

Follow the winding road inland to Vine Street Café, a quaint cottage restaurant serving high-grade American classics made with produce straight from local farmers and fishermen. Modern trattoria 18 Bay, on North Ferry Road, is something of a Shelter Island institution. The four-course set menu changes weekly, but is always Italian-inspired, including an antipasti quartet and handmade pasta.

 

Local cafés

Down by the harbour, Marie Eiffel Market is Shelter Island’s own little piece of Paris. The breads and pastries are baked in-house, and the artisan cheese selection is the star of the gourmet-grocery show at the deli. The lobster roll is small but oh-so-perfectly formed, and the best spot to enjoy it is out the back on the over-water decking.

 

Local bars

For DJ-sets and seaside cocktails with the hip Hamptons crowd, head to Sunset Beach hotel. Salt is a buzzy dockside bar and grill on the south side of the island; try the house beer or signature Dark ‘n’ Stormy.

 

Reviews

Photos The Chequit reviews
Rosa Park

Anonymous review

It’s just over a two hour drive from Manhattan, yet it feels aeons away from the breakneck pace of city life. The eight minute ferry ride from Greenport to Shelter Island provides a moment for some tentative rehabilitation to begin, preparing my New York self for this slow, sleepy enclave.

After a stroll up a gentle hill, I wheel my suitcase to the front porch of the Chequit. Having the fortune to arrive at happy hour, I am soon clutching a glass of chilled Sauvignon Blanc and receiving a pearly smile from the lady at the front desk. She chats to me like we’re old friends as she kindly walks me through the practical details of my stay.

The Chequit is summery cheer and homey nostalgia at every turn. I feel as though I’ve come to stay at the rambling beach house of my favourite (and most stylish) aunt for the weekend –  if I had such an aunt that is.

The beautiful renovation of this 1870s Methodist building evokes the charm of the island’s Forties heyday, but its luxury is tailored for modern travellers – all cosy nooks, velvety plushness, and cool comfort. Canary yellow accents sing, soft pinks blush, and deep greys keep it grown up, all underlined by the beautiful blonde of restored hardwood floors. Hints of vintage may abound, but there’s not a doily or a patch of chintz in sight. A grand piano in the far right corner of the drawing room catches my eye. My head fills with romantic images of 19th-century parlours and Henry James novels, but I’m too shy to play.

Dotted around the communal spaces are hurricane candle holders and tall, brass candelabras. Everything may be pristine and perfectly managed, but friendly hospitality is communicated subliminally by well worn, lived-in details, and reflected in the truly personal service. There is no pretense here; everyone is welcome, whatever your chosen holiday-ing style. Mine being lying low, I quickly adopt the tall linen-covered armchairs in the drawing room as my favourite hang out.

My newfound personal sanctuary aside, the drawing room is where the action happens – the action consisting of breakfast-taking between 7-10:30am and wine/tea-sipping from 4-8pm.

Breakfast is accompanied by soft classical music; the crunch and crackle of newspapers; the gentle early morning hum of well-rested guests starting their day. I tuck into my hearty spread of chia pudding with yogurt and fresh berries, baked eggs and asparagus, and blueberry muffins. As you would hope, all are seasonal, fresh, locally grown, homemade – and delicious (as are the ‘breakfast cocktails’).

The Chequit has an arsenal of delightful solutions for the summer heat. These include rain head showers complete with CO Bigelow products, which fill the room with citrus-and-herb aromas, and the fluffiest of summer-weight duvets. Of course, the most quintessential is the wide, inviting, beautifully furnished porch, which wraps around the property like a hug.

There are couches aplenty stacked with pillows and blankets, vibrant palms and flowers, and more rocking chairs than I’ve ever seen in one place. The rocking chair, for me, is a symbol of unadulterated leisure. On my final afternoon I embrace this great East Coast trapping, choosing to while away some time taking in the view and savouring the gentle breeze.

While the terrace – strewn with mismatched chairs and tables, and strung with pretty lights – is made for devouring oysters and clams in the fresh salty air, I opt for dinner at the Red Maple restaurant.

As I read my book and demolish my flatbread, in pleasant anticipation of a comforting New England style entrée, I notice the sweet feeling of luxury that comes with a fading sense of urgency. I should take the ferry more often. 

 

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