Weekend holidaymakers will be spending the bulk of their time sunning and swimming, but East Hampton is a retail hub where you can find more than just a pair of swimming trunks and a boogie board. The Aerin, Gucci and Altuzarra boutiques are havens for stylish folk, along with Ralph Lauren’s RRL barn, where visitors come for the one-off RL finds and stay for the idyllic gardens and rigorously produced mise-en-scène. Those who stay fit pop into Mr Jimmy Minardi’s beach workouts or hit the road on their bikes. “I’m a big biker and The Hamptons has really amazing and well-kept mountain biking trails,” says Brinkley-Cook. “My go-to is the Paumanok trail system off Route 114 in East Hampton.”

There’s considerable star wattage woven into this idyllic setting too, with the occasional famous face popping up. “My favourite neighbour is Julianne Moore,” says Mr Matt Albiani, a photographer and Style Council Member. “Whenever we pass each other on a beach walk, I’m greeted with the best smile and a genuine hello. She is just the best.” Interior designer Mr Nate Berkus can be found there, too. “I love stopping by Round Swamp Farm for snacks and walking across the street to the beach,” he says.

Additional recommendations

• Moby’s, a coastal Italian eatery founded by Aussies Messrs Lincoln Pilcher and Nick Hatsatouris.

• Pollock-Krasner House, the preserved home and studio of artist Mr Jackson Pollock and his wife, Ms Lee Krasner.

• Minardi Training for beach workouts to work off your dinner.

• The Monogram Shop, a mom-and-pop shop where nearly anything can be emblazoned with your crest or initials.

North of East Hampton, you’ll find Sag Harbor, where a mix of well-heeled New Yorkers rub elbows with a more arts-minded community. Situated in the harbour itself is Le Bilboquet, which becomes a clubhouse of sorts for locals and visitors, thanks to its expansive outdoor seating and a bar scene that’s known to party on until the wee small hours. For a sweeping sunset, gallerist Mr Robert Stilin prefers Long Beach or the deck at The Beacon, or taking a small journey to Sunset Beach, situated on the shores of nearby Shelter Island and accessible by a brief ferry ride. “In the summer on a sunny day, there is nothing better than dinner and a drink on the upper deck,” he says.

Nearby, there’s Wölffer Estate Vineyard, one of the few remaining vintners still located on the South Fork, where the Wölffer family can often be found leading tastings and tours. They’re known best for their Summer In A Bottle rosé, which is seemingly consumed in gallons between Memorial Day and Labor Day, the unofficial start and finish of the Hamptons season.

Additional recommendations

• Loaves & Fishes Foodstore, a beloved local shop for provisions and prepared foods.

• Estia’s Little Kitchen for the best breakfast burritos in town.

• Menard Acupuncture, a traditional Chinese medicine clinic run by Mr Kevin Menard.

• Onda Beauty, the natural, clean and non-toxic beauty retailer founded by Mses Larissa Thomson, Naomi Watts and Sarah Bryden-Brown.

• Marie Eiffel Market, dockside organic market and café that prepares a catch of the day and allows guests to bring their own wines.

En route to the end of the world (see below) and the most relaxed option when it comes to Hamptons hamlets, Amagansett maintains a subdued air with a tight-knit community that often congregates on its Main Street, which spans just two blocks and one town square. Here, you’ll find cult favourite lunch spot Hampton Chutney Co, which serves up foot-long dosas, along with the Stephen Talkhouse, or just Talkhouse for short, where Coldplay and Mumford & Sons have been known to perform an impromptu gig.

Slightly off the beaten path is Maidstone Park Beach, which Mr Aki Suzuki, the former general manager of Scarpetta Montauk and now head of American Cut Steakhouse in Tribeca, frequents for sunsets and the occasional kiteboarding excursion, weather permitting. Otherwise, the gusts in Napeague Harbor are preferred.

Additional recommendations

• Vinnie & Nick’s Barber Shop offers traditional cuts and shaves.

• Stuart’s Seafood Market, a no-frills seafood shop with an equally no-frills but incredibly tasty lobster roll.

• Cavaniola's Gourmet, family-owned gourmet cheese shop.

• Love Adorned for eclectic jewellery, homewares and vintage finds.

The farthest point east and often referred to as “the end of the world”, Montauk was once a haven for commercial fisherman. These days, while it still has several operating ports, it’s also a centre of gravity for those looking for a good time. The Surf Lodge, Hero Beach Club and Memory Motel, once a hangout for The Rolling Stones, are longstanding hives of action, along with The Crow’s Nest, where Albiani can often be found enjoying a sunset cocktail. “There is no place more magical,” he says. “Have a cocktail down by the water and then head up to the restaurant when they call your name. Magic!” During the day, it’s Duryea’s Lobster Deck, where yachts often rock up for pricy provisions such as the decadent lobster Cobb salad and plenty of rosé.

For some highlights slightly off the beaten path, founder of Montauk Brewing Company Mr Vaughan Cutillo of course recommends a visit to his own brewery, where basketball ace Mr JJ Reddick and singer Lady Gaga have been known to appear, followed by The Dock, a dive bar where phones are strictly forbidden. “Don’t say I didn’t warn you,” he says. “But really, the list of dinner options is endless – Inlet Seafood, Shagwong, The Point, Harvest. I could go on and on. Just pop in to any spot and support local.” To work it off, he looks to Dan Good Yoga and Truth Training, when he wants to be pushed to his limits. “I didn’t know humans could sweat that much,” he says.

Additional recommendations

• Deep Blue Vintage at The Montauket Hotel, a tightly curated selection of vintage clothing and antiques.

• Best Pizza & Dive Bar, newly-opened pizza joint with frozen cocktails.

• Ditch Witch, sandwich and sushi truck at the entrance to Ditch Plains Beach.

• Cashin Coffee Roasters, coffee purveyor offering weekend pick-up of freshly ground coffee beans at its Montauk roastery. Dawn Patrol roast is the crowd favourite.

• John’s Pancake House, a diner that’s as famous for its crowds as it is for its pancakes.

• Showfish at Gurney’s Star Island, a new outpost of the famous Gurney’s Hotel.

• South Etna, a charming gallery in the centre of town, opened in 2020 by Ms Amalia Dayan and Mr Adam Lindemann. The gallery’s sign was painted by American artist Mr Julian Schnabel.