How To Take A Local’s Tour Of The Hamptons


The Hamptons, a bustling cluster of historic villages, is where New York City people go in the summer to enjoy the lovely sandy beaches, outdoor eating, and cozily sumptuous summer houses with wood shingles. Geographically speaking, the Hamptons are located immediately east of NYC on the South Fork of Long Island, extending from West Hampton to Montauk, or “The End,” as it is known to the locals. In this East-end neighborhood, having a summer home is wonderful, but it’s not essential to visit the restaurants, farm shops, wineries, and sandy beaches that have won over visitors from all over the globe in addition to New Yorkers.

These are the greatest spots to dine, stay, and party in the Hamptons, where dreams are made over delicious meals and tan lines persist.

Places To Stay

When visiting these beachy tiny villages, discovering the minor differences between them is half the joy (although I’d say that when seeking for a home base, choose the perfect spot to stay may make all the difference). Anything between Bridge Hampton to Amagansett would provide a welcoming escape from the city’s turmoil if you’re seeking it. Even the harshest hotel reviewers will be impressed by an extravagant stay at the Topping Rose House, a renovated 19th-century estate tucked away in Bridge Hampton where old architecture combines effortlessly with the reinvented contemporary style and flair.

The Roundtree, Amagnesett’s latest boutique hotel, may have just debuted in 2020, but the structure itself goes back centuries if it’s historic grandeur you’re looking for. These charming cottages have a traditional wood-shingled facade and ooze elegance and easy-going comfort. The shared garden is furnished with lounge chairs, plush sofas, colorful foliage, and a real s’mores station in the evening.

The Roundtree

The Roundtree

The more boisterous groups often go to Shelter Island or Montauk, just north of the action, for some fun in the sun. There are still several first-rate lodging options available, even though they are often the final few reasonably priced districts in the city. For instance, the Sunset Beach Hotel on Shelter Island has umbrellas with yellow and white stripes, glittering lights, and ice-cold frosé that make it resemble St. Tropez. Further east, Gurney’s Montauk Resort & Seawater Spa attracts the affluent travelers who want to be seen and heard, while The Surf Lodge continues to rule the roost for warm California vibes and live music. This is the nicest location to be on a Sunday, trust me on that.

A Place To Eat

While I like having a wide variety of restaurants to select from in New York City, part of the appeal of touring the South Fork of Long Island is enjoying the many farm- (or sea-) to-table cafes that provide not just fantastic cuisine but also some very enticing atmosphere. With so many premium restaurants to choose from, including French dinners like Le Bilboquet and Jean George’s farm-fresh diner at the abovementioned Topping Rose, you’re sure to run into a star or two. Speaking of famous people, Tutto Il Giorno, a must-try for traditional pasta accompanied by trendy and airy design in Southampton and Sag Harbor, was founded by the husband-and-wife team of Gianpaolo de Felice and Gabby Karan de Felice (also known as fashion queen Donna Karan’s daughter).

Tutto Il Giorno Restaurant

Tutto Il Giorno Restaurant

But at the other side, I’d argue that lobsters is the island’s true star. After all, what would a summer in New England be without a few pounds of lobster? While enjoying the new cut of the day at Duryea’s Lobster Deck in Montauk, the viewpoints will help you believe as though you’ve walked into another moment in history. Nevertheless, most local residents (myself included) will inform you that the finest lobster wraps are found at the seafood cottage in Amagansett recognized as The Lobster Roll, also known as “Lunch,” thanks to the large sign which settles at the front of the gate.



After you’ve had your fill of seafood, no trip to the Hamptons would be complete without stopping at one of the region’s farm stands, like Round Swamp Farm and Amber Waves Farm, or taking a stroll along the famed Hamptons Wine Trail, where glasses of rosé—a Hamptons staple—are never empty at wineries such as Wölffer Estate, Channing Daughters Winery, as well as Shelter Island’s latest cocktail bar, White Oak Wine Garden.

What to watch

Coopers Beach in South Hampton is among the Hamptons’ most well-liked resorts, and with good reason. In fact, Stephen Parker Leatherman, commonly known as Dr. Beach, an American geologist, coastal biologist, and author, consistently ranks as being one of the best US beaches (who rates beaches around the world). The beach stretches for kilometers, is bordered by lovely dunes, is covered with thick native beach grass, and is sporadically dotted with opulent mansions. The ideal place to start the morning surrounded by nature is to the east, on the Walking Dunes Trail in Hither Hills State Park. If you’re ready for a little sport and adventure, you can also take a picturesque bike ride to the Montauk Point Lighthouse, which is the most recognizable structure on the South Fork. From there, you can climb the lighthouse to take in the vista and watch surfers attempt to hang ten below.

There are many stylish shops, spa getaways, and a noteworthy art scene to keep you busy on days when the weather simply won’t seem to comply. Some claim that the Hamptons’ scenic appeal attracted artists like Jackson Pollock and Lee Krasner, whose home is now on display close to East Hampton, and also writer, designer, and landscaper Robert Dash, who founded Sagaponack’s Madoo Conservancy.

Most of those Hamptons’ quirky and whimsical businesses, like Gwyneth Paltrow’s first Goop brick-and-mortar store, can be found if you go back north to Sag Harbor. Contrarily, Bridgehampton is more well-known for its stores that sell items for the Hamptons uniform, such as elegant white linens and natural slip outfits à la Communitie, a brand started by another one of my favorite artists, John Patrick. The residents, like me, congregate to JECT, a boutique aesthetic salon a few steps below Community for all matters facials, skin care, and Botox. After your skin has been revived, go to East Hampton where you may treat yourself to a deep-tissue treatment at the Naturopathica Spa & Healing Center (which only employs natural and organic materials for total relaxation).

Naturopathica Spa & Healing Center

Naturopathica Spa & Healing Center

Once you’ve recovered from your East End Weekend, be sure to start making preparations for your next trip since lodging and summer houses in this area tend to sell out well in advance. Life in the Hamptons is just as delightful in the off-season as it is in the summer, even after the white linen tables have been put away, the tenants have gone home, and the patio umbrellas have been taken down.

It’s really one of the few untouched locations where you can relax in the great outdoors, immerse yourself in art and history, and indulge in a special supper or two without having to sacrifice quality. Finding seclusion and tranquility on this beach paradise “Out East” proven time and time again to be amongst the greatest ways to spend a New England summer, despite the fact that this seaside playground would always attract large crowds.



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