How To Soak In The Final Weeks Of Summer In The Hamptons

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vacation guide to hamptons

It’s that time of year. This mid-summer season sees the Hamptons filled to the brim with East Coasters looking 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 area spans across Long Island’s South Fork from West Hampton to Montauk — or as the locals call it, “The End”— just east of NYC. And this summer, every inch of it will be charged with seasonal activities, pop-ups, events, and general festivities, solidifying it as the epitome of summer destinations. And while it's certainly nice to have a home 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 three 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

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. Speaking of the latter, the iconic hotel and restaurant will be kicking off its Summer 2023 Concert Series, running from May 26 through September 4. Its weekly musical acts include big names like Aloe Blacc, Busta Rhymes, ARIZONA, DJ Cassidy, Blondish, Lauv, DJ Pee Wee of Anderson Paak, Fisher, Lauv, and more. This is a can’t miss.

In Sag Harbor, Maison Margiela has partnered with celebrity stylist Cameron Silver for his second annual East Coast Summer fashion residency at Sage & Madison. As part of the partnership, Margiela is taking over the hotel’s dining room space for a pop-up experience running through July 31, which will include women’s ready-to-wear, accessories, and shoes highlighting the label’s new colorama handbags and the iconic 5AC styles from the CoEd23 Exit 1 Collection.

Where To Eat

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.

Where To Beach

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.

Where To Shop

On days when the weather just won’t seem to cooperate, there are plenty of chic boutiques 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.

Also, the CHANEL Ephemeral Boutique in East Hampton is now reopened for the summer. The 2,500- square-foot two-story shop has been reimagined for the season as a “perfectly Parisian summer fantasy” according to a press release. Offering a luxe selection of handbags, small leather goods, accessories, watches and fine jewelry, fragrance and beauty, as well as the Coco Beach and Métiers d’art 2023-24 collections by Virginie Viard, this little haven will certainly provide some much needed retail therapy.

And, while you’re on the East side of town, swing by Loewe’s new permanent store on Main Street, opening on August 2. Decked out in brightly colored natural fiber carpets, cool Utrecht chairs, and traditional Loewe handmade ceramic tiles, the shop is an experience in itself. A full range of men and women’s offerings will be available, including ready-to-wear, handbags, shoes, jewelry, and home scents.

Where To Pamper & Refresh

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.

Knockout Beauty Bridgehampton is also a great place to spend your Memorial Day holiday weekend. On May 26 and 27, renowned esthetician Ludmila Daletskaya will offer facials before returning to her homebase of NYC. However, should your need for indulgent beauty treatments arise throughout your post-holiday Hamptons stay, the Hamptons shop will reopen for the summer on June 28, offering facials from Wednesday to Saturday.

And if you happen to find yourself in the Hamptons between June 16 and July 7 be sure to book an treatment with the GOAT of all dermatologists Dr. Macrene Alexiades, who will be there for a limited residency. The skin care expert, who holds a whopping three Harvard degrees, a BA in Biology, an MD and PhD in genetics, offers 55 technologies to treat a range of concerns, including body sculpting treatments such as NuEra, Profound, and Morpheus.

And come August 4, JLo Beauty will have a weekend residency at Curio @ Project Hamptons, ending on August 6. Swing by to try the brand’s most popular products, including That JLo Glo Serum, That Big Screen Broad Spectrum SPF 30 Moisturizer, and the JLo Body collection’s Firm + Flaunt Targeted Booty Balm.

For more cutting edge body treatments, pay a visit to Dr. Anne Chapas newly opened UnionDerm Hamptons location. The beloved dermatologist’s third aesthetics destination, this buzzy locale will cater to all your toning and tightening needs (sans downtime), with services like Accufit and Sofwave at your disposal.

And for those looking to add some movement to their summer vacation plans, Tracy Anderson’s Hamptons Vitality Week is certainly for you. Taking place in the instructor’s Sag Harbor studio in July and August, these designated weeks will feature festivities celebrating the one-year anniversary of TA’s full-body, holistic MYMODE program. The agenda includes MYMODE classes and lectures with Anderson herself, morning coffee receptions, and state-of-the-art health experiences. Be sure to reserve your spot quickly, as these will likely be sold-out events!

The Hamptons is 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.

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