How To Explore The Hamptons Like A Local

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vacation guide to hamptons

A vibrant collection of historic towns, the Hamptons is where New York City residents flock come summer to soak in the idyllic sandy beaches, al fresco dining, and cozy wood-shingled summer homes that are every bit as charming as they are opulent. Geographically speaking, the Hamptons spans across Long Island’s South Fork from West Hampton to Montauk — or as the locals call it, “The End”— just east of NYC. While it's certainly nice to have a summer house in this East-end enclave, it’s not necessary when it comes to exploring the local eateries, farm stands, vineyards, and sandy shores that have captured the hearts of not just New York natives, but people from all over the world.

Having lived in the Hamptons for the last two years, what I miss the most about this urban escape isn’t the celebrity sightings or extravagant restaurants, but rather the way the salty air smells at dawn, the sound of the waves, and the friendly smile you get from a local who you’re sure you’ve seen once or twice before. The South Shore is not just a way to relax and get away from it all, for most it’s a home away from home that never ceases to deliver on unforgettable memories. From memories shared over exquisite meals to tan lines that never seem to fade away, these are the best places to eat, stay, and play in the Hamptons.

Where To Stay

Gurney’s Montauk Resort & Seawater Spa

Exploring the subtle nuances between towns is half the fun when it comes to checking out these beachy small towns (although I'd argue when it comes to looking for a home base, choosing the right place to stay can make all the difference). If you’re looking for a serene refuge from the chaos of the city, anywhere from Bridge Hampton to Amagansett will provide a cozy reprieve. For over-the-top luxury, an ultra-posh stay at the Topping Rose House, a reimagined 19th-century mansion nestled in Bridge Hampton where traditional architecture blends seamlessly with the reimagined modern design and flair, will impress even the toughest of hotel critics.

Although if it’s historic architecture you seek, Amagnesett’s newest boutique hotel, The Roundtree, may have only opened in 2020, however, the building itself dates back as far as the 17th century. With a classic wood-shingled exterior, these cozy cottages exude elegance and laid-back relaxation with a communal backyard adorned with lounge chairs, comfy couches, vibrant greenery, and a proper s’mores station come nightfall.

Just north of the action, the livelier crowds tend to flock to Shelter Island or Montauk for a little sun and fun. While these tend to be the last few affordable areas in town, there are still plenty of top-notch accommodations to choose from. Shelter Island’s Sunset Beach Hotel, for example, is reminiscent of St. Tropez with its twinkling lights, yellow and white striped umbrellas, and ice-cold frosé. Farther out east, you’ll find the luxury enthusiasts shacking up at Gurney’s Montauk Resort & Seawater Spa to see-and-be-seen while The Surf Lodge still reigns king for cozy Cali vibes and live music. Trust me when I say, this is the coolest place to be on a Sunday.

Where To Eat

Courtesy of Wölffer Estate

While there’s nothing I love more than having my fair share of restaurants to choose from in NYC, part of the charm of visiting the South Fork of Long Island is experiencing the several farm- (or sea-) to-table eateries that, in addition to great food, serve up some serious ambiance. From French affairs at Le Bilboquet to Jean George’s farm-fresh eatery at the aforementioned Topping Rose, you’re guaranteed to rub elbows with a celebrity or two as upscale eateries are in no short supply. Speaking of celebrities, Tutto Il Giorno opened by husband and wife duo, Gianpaolo de Felice and Gabby Karan de Felice (aka fashion icon Donna Karan’s daughter), with friend, David Mayer, is another must for authentic pasta complemented by chic and airy decor in Southampton and Sag Harbor.

On the other hand, I’d contend that the real star on this island is — lobster! After all, what's a New England summer without a pound of lobster or two? The views at Duryea’s Lobster Deck in Montauk will make you feel like you’ve stepped into another place and time while cracking open the fresh catch of the day, however, most locals (including myself) will tell you the best lobster rolls come from the seafood shack in Amagansett called The Lobster Roll — better known as “Lunch” —thanks to the huge sign that sits in front of the entrance.

Once you’ve had your fair share of seafood, no visit to the Hamptons would be complete without exploring the local farm stands, like Round Swamp Farm and Amber Waves Farm, or the infamous Hamptons Wine Trail where glasses of rosé (a Hamptons staple) are always overflowing at vineyards like Wölffer Estate, Channing Daughters Winery, and Shelter Island’s newest wine bar, White Oak Wine Garden.

What To See

Courtesy of JECT

One of the most popular beaches in the Hamptons, and rightfully so, is Coopers Beach in South Hampton. In fact, it ranks as one of the top US beaches year after year, by Stephen Parker Leatherman, also known as Dr. Beach, an American geoscientist, coastal ecologist, and author (who rates beaches around the world). The beach is miles wide, backed by picturesque dunes, adorned with tall native beach grass, and intermittently sprinkled with a decadent mansion or two. To the east, the Walking Dunes Trail in Hither Hills State Park is the best way to start the morning immersed in nature. Or for a little sport and adventure, a scenic cycle down to the South Fork’s most iconic landmark, the Montauk Point Lighthouse, will delight you as you hike up New York State’s oldest lighthouse while enjoying the view and watching surfers try their best to hang ten below.

On days when the weather just won’t seem to cooperate, there are plenty of chic boutiques, wellness retreats, and an impressive art scene to occupy your time. In fact, some would argue that the Hamptons is so picturesque, it’s drawn in creatives such as Jackson Pollock and artist Lee Krasner, whose house is on exhibit near East Hampton, as well as artist, writer, and gardener Robert Dash, who created Sagaponack’s Madoo Conservancy (which provides a refreshing reprieve from the harsh sun as you stroll through the perfectly manicured gardens).

If you head back north to Sag Harbor you’ll find many of the Hamptons’ quirkiest and most playful boutiques, including Gwyneth Paltrow’s first Goop brick-and-mortar shop. Bridgehampton, on the other hand, is better known for its boutiques that cater to a Hamptons uniform, AKA chic white linens and organic slip dresses a la Communitie founded by one of my favorite designers, John Patrick. A few steps down from Communitie, you’ll find JECT, a boutique cosmetic spa where the locals, myself included, gather for all things Botox, skin care, and facials. Once your skin is refreshed, head over to East Hampton where you can indulge in a deep-tissue massage at the Naturopathica Spa & Healing Center (which only uses organic and holistic products) to melt away the stress of city life for complete relaxation.

After feeling rejuvenated from your East End Weekend, be sure to get a jumpstart on your plans for your next visit as hotels and summer homes tend to book ahead well in advance here. Even long after the white linen tablecloths are tucked away, the renters go home, and the patio umbrellas come down, life in the Hamptons is every bit as charming in the off-season as it is in the summer.

It’s truly one of the few unspoiled places to unwind in nature, immerse yourself in art and history, and treat yourself to an upscale dinner or too, without having to compromise on quality. While this coastal playground will always draw in the masses, finding solitude and solace on this seaside paradise “Out East” proves time and time again to still be one of the best ways to enjoy a New England summer.