How to Spend the Perfect Long Weekend in the Hamptons
In the summer, New Yorkers are packing their white linens and heading to the Hamptons. The eastward summer Friday migration sees groups of 20-somethings piling onto the Jitney (a dedicated bus to the Hamptons) and the Long Island Railroad, equipped with rosé to set the scene. Some weekenders will opt to hack the traffic and drive out from the city, which can be convenient for getting around once you’re actually there. And, some will splash out on helicopter rides and seaplanes for the most glamorous of arrivals.
Each year, the Hamptons attracts groups of friends, families, and the 0.001% that escape to the kind of properties seen in Sotheby’s catalogues where eight-figure listings are the norm. Different crowds gravitate towards different areas: in Montauk it’s all about the music, surfing, and late nights; East Hampton and Southampton tend to draw more refined groups, couples, and billionaires; and Sag Harbor has traditionally been more low-key and family-oriented.
The region has very stringent building regulations, so unlike many seaside holiday destinations, you won’t find any hotel chains, which, in many ways, adds to its charm. It does, however, make it essential to plan well in advance due to limited accommodation options. Timeshares are one way to go (but you generally need a solid group and it can be quite expensive), and Airbnb also has a presence, but what you get for your money could often be better spent on a long weekend in the Caribbean. There are several boutique hotels that are highly recommended, but getting in early is vital as they tend to book out. Similarly, it’s worthwhile making reservations at popular restaurants in advance as crowds escalate during the height of the season and getting a good table on a Saturday night can be dicey.
But, like the concrete jungle itself, the Hamptons seems to reinvent itself each year and the start of each season brings new bars, restaurants, hotels, and pop-ups that quickly become hotspots, ready to be geotagged. Whether you’re interested in the new or the time-honored establishments, we’ve charted the best places to visit in the Hamptons.
Where to stay
Gurney’s Star Island Resort & Marina
Gurney’s Star Island, a 107-room resort that is located on the largest marina in the Hamptons, is a new player to the scene. The luxury enclave features a private beach, two outdoor pools, a kids’ club, and an upscale restaurant called Showfish, which has a menu built around seasonal ingredients and seafood delivered directly to the docks by local fisherman.
Shou Sugi Ban House
The launch of Shou Sugi Ban House marked the Hamptons’ first comprehensive wellness retreat, filling a glaring gap in the market. The private three-acre sanctuary has thirteen guest studios, a spa with hydrotherapy pools and a roof deck, a fitness center, organic vegetable gardens, a library, and a Healing Arts Barn. Holistic wellness practices are customized to each guest and designed to revive even the most jaded New Yorker.
Baker House 1650
One of the most gorgeous B&Bs in the Hamptons is Baker House 1650, which is like being welcomed into the home of a friend with excellent taste. It’s cozy yet luxurious with plush furnishings, well-appointed suites, sprawling gardens, a spa, and three pools. If you were looking for a wedding venue or a place to host a special event or a garden party, this would be a great location.
Topping Rose House
Topping Rose House is one of the stateliest properties in Bridgehampton and one of the few hotels that remains open year-round. There is a pool, a Jean-Georges restaurant, a spa, a library and a complimentary car service that transports guests from the beach to dinner and anywhere else they may desire within a 2-mile radius.
Sunset Beach is one of the latest projects by legendary hotelier, André Balazs — the man behind Chateau Marmont, The Mercer, and The Standard. It’s located on Crescent Beach in Shelter Island and it has only twenty guest rooms, so it’s an intimate escape. The style is low-key but elevated — perfect for couples.
Gurney’s is the only luxury hotel in the Hamptons that is located right on the beach — a major highlight that has kept it firmly set at number one. The resort has 146 rooms, suites, and beachfront cottages, each with panoramic ocean views and access to The Beach Club, which packs out early during summer weekends, especially if you’re wanting to secure a cabana. It’s also home to Scarpetta Beach, an Italian restaurant which is one of the best dining experiences out east.
Baron’s Cove underwent a major renovation in 2015, and the result is an elegant, nautical-inspired resort with 67 guest rooms and suites. Highlights include the waterfront pool framed with sun loungers, a tennis court, the seafood-centric restaurant (in particular, the fresh lobster rolls), and the cocktail bar, complete with a pianist. There’s also live entertainment every night during the summer and guests can enjoy yoga sessions and various watersport options.
Hero Beach Club
Definitely one for younger groups and those setting out to embrace Montauk’s party scene, Hero Beach Club is a low-key hotel with 34 rooms that look like they’ve been outfitted entirely in West Elm. It has a pool surrounded with daybeds, and is located right by the beach.
Where to shop
Cult lifestyle brand goop is open in twoa brick-and-mortar locations in Sag Harbor and Amagansett. Here you'll find a beautifully curated mix of beauty, fashion, home, and wellness items and a series of cocktail parties, wellness workshops, family days, and various events throughout the season.
Serena + Lily
For a hit of interior décor inspiration, step into Serena + Lily where you’ll find a whitewashed mix of coastal Californian furniture, woven baskets, elegant homeware, lighting, and art.
Need a book to read while lounging by the pool? Look no further than BookHampton, which has a wide selection of fiction and non-fiction novels, coffee table books, and educational books for children.
Zimmermann’s collections are fit for the world’s most chic beach destinations. Last year, a boutique was set up in Saint-Tropez, and this year, a pop-up launching in Capri. The Australian-born brand has had a space in East Hampton for several seasons now, and it’s become a destination for elevated summer essentials. If you’re looking for a beautiful floral blouse, a stylish kaftan to throw over a bikini, or a feminine cocktail dress, this is the place to go.
For a smart-casual mix of men’s and women’s clothing and accessories, head to Club Monaco in East Hampton. The Ralph Lauren-owned brand offers timeless essentials to suit any Hamptons occasion and translate well back in urban territory.
Stepping into LoveShackFancy feels like being on a movie set from a bygone era where girls wear lace dresses and hats with ribbons and vibrant peonies are in full bloom. The boutique opened in Sag Harbor last summer with an ultra-feminine mix of clothing and accessories for women and little girls, artfully arranged in a French country-style setting.
Consider this your go-to for anything beauty-related, whether it’s a Moroccanoil hair mask to revive salt-drenched locks or to collect Dr. Barbara Sturm’s travel-sized essentials kit if you’ve left your skincare at home and need reviving. There’s also a beautiful mix of candles and fragrances on offer including Tom Ford’s appropriately summery Neroli Portofino and Jo Malone’s popular diffusers.
AYR Beach House
Located in Sag Harbor, AYR’s Hamptons outpost offers the uniform essentials that it has become renowned for: denim, shirts, slip dresses, and jackets. “We wanted to offer a range of pieces that are core to our DNA and also a mix of items that capture a beach town sensibility,” says AYR’s creative director, Jac Cameron.
Local favorite, Carissa’s The Bakery, is slated to open a new 3,500-square-foot space in East Hampton this season, which will include a bakeshop, a large production area for crafting signature pastries and breads (including the renowned pickled rye), and a restaurant, which will serve wine and cocktails and will have outdoor seating for dining al fresco. Homemade gelato, soups, and sandwiches will also be on offer.
Acclaimed chef Terrence Brennan recently opened his first restaurant in Southampton, called Blu Mar, occupying the former Maison Vivienne space. It is open for lunch, dinner and weekend brunch and serves Mediterranean-inspired menus.
Located in the heart of East Hampton village, Babette’s has been the go-to brunch spot since 1995. Here you will find modern, healthy cuisine in a casual café setting with photos of celebrity regulars lining the walls. The atmosphere is unpretentious and the servings are generous. It’s particularly notable for its wide range of egg dishes (benedicts, omelettes, huevos rancheros), and freshly squeezed juices.
Highway Restaurant & Bar
It looks like a diner on the outside, but step into the Highway Restaurant & Bar and you’ll find an elegant space serving New American cuisine with international influences. It’s under the same management as Eleven Madison Park, Charlie Bird, and the Restaurant at the NoMad Hotel, and the group’s high standards are on show.
Jean-Georges at Topping Rose House
Like some of Jean-Georges’ hotel-affiliated restaurants in New York (including locations at PUBLIC, The Mercer, and The Mark), the Topping Rose House outpost offers classics like the black truffle pizza, spicy tuna tartare, and the peekytoe crab cakes. The wide variety of entrees leaves little to be desired, with a long list of options to appease any palette. Also, it’s a good spot for a cocktail in the evening.
The American Hotel Restaurant
If you want to be serenaded by a tuxedoed pianist during dinner service in a historic, character-filled setting, The American Hotel Restaurant is one to book in. The Sag Harbor establishment first opened in 1846, and with much of the original architecture still intact, it feels like being transported to another era. The food is classic American and the bartender makes excellent textbook cocktails.
The Golden Pear
The Golden Pear is the place to go for coffee that’s a step up from Starbucks. There are locations in Bridgehampton, Southampton, East Hampton and Sag Harbor, all of which also offer salads, pastries and simple food that’s a good option if you’re on the move (though, if you’re shopping for a beach picnic, it’s best to head to Citarella which has locations in East Hampton, Southampton, and Bridgehampton).
The name ‘1770 House’ refers to the year that this Hamptons icon was first recognized as an inn. It has amassed a lot of history since the 18th century, and today, it remains one of the best dining destinations in the Hamptons. It offers special tasting menus, a la carte, and an excellent wine program.
Like its New York City locations, Sant Ambroeus Southampton serves classic Milanese cuisine in an ‘80s-style setting. It’s a reliable spot for a pasta and a piece of cake from the display cabinet. Head there for lunch and wander around the village.
Page at 63 Main
This Sag Harbor restaurant is devoted to serving organic cuisine, utilizing fresh produce from its own aquaponic gardens. It’s family friendly and has crowd-pleasing menus featuring salads, seafood, sandwiches, pasta, and entrees alongside a bar menu with shared plates of sliders, burgers, and crispy calamari.
Things to Do
Parrish Art Museum
The Parrish Art museum is to the Hamptons what The Whitney is to Manhattan. It features a variety of ultramodern and, sometimes, unconventional works from notable artists. Perhaps the most impressive exhibition on show currently is "Picture," which includes photorealism style paintings and juxtaposed figures from Michaelangelo’s Sistine Chapel ceiling.
Wölffer Estate Vineyard
Come right to the source of Instagram’s most photogenic rosé (Summer in a Bottle) and enjoy wine tastings, live music, and a picnic by the vines. It’s a gorgeous spot to set up with friends and family at sunset.
Guild Hall is an established, multidisciplinary arts center, with a mix of everything from live Cuban music performances to art exhibitions and film festival screenings. Check the website for a list of events coming up this season.
Sag Harbor Whaling & Historical Museum
Particularly popular with families, the Sag Harbor Whaling & Historical Museum presents a glimpse into the village’s rich history. There are also contemporary exhibits on display.
Each season, The Breakers is known to host a number of fashion, lifestyle, and wellness pop-ups, and recenetly started a series of HIIT classes by Nomad East Fitness along with bootcamp and yoga sessions with EIR NYC and Starfysh.
Southampton Hunt & Polo Club
Learn how to play polo at Southampton’s Hunt & Polo club, which offers classes for all levels. It’s also open to the public for watching tournaments.
On the easternmost point of Long Island lies Montauk Lighthouse — a historic site that hosts a wide variety of events and festivals.
The Surf Lodge
The Surf Lodge is always a hive of activity during the summer, hosting a constant flow of concerts and events.
If you’re up for a big night, head to Stephen Talkhouse in Amagansett, which is renowned for its live music. The rustic venue has played host to some of the industry’s most notable acts, including the Rolling Stones and Paul McCartney. On a regular night, you’re more likely to encounter a local band and a rowdy mix of Manhattanites that are 12-beers-plus deep.
The Montauk Beach House
A major part of Montauk’s social scene is Montauk Beach House, which has pop-up boutiques, wellness sessions, and live DJs through into the night. A great spot to go with a group for the evening.
Located in the former 1 Oak space, AM Southampton is a place to go if you’re into bottle service and the classic nightclub scene.
Ask anyone what their favorite beach is in the Hamptons, and chances are they’ll say it’s Cooper’s Beach, which has pristine white sand and never gets too packed. It’s an appealing destination to park up for a day of sun and relaxation with a civilized crowd.
Atlantic Avenue Beach, Amagansett
Families, groups and singles alike flock to Amagansett’s Atlantic Beach, which is a popular spot during the height of the season. You can rent umbrellas and beach chairs for the day, and there is a casual takeout joint called the Beach Hut where people go for milkshakes and burgers.
East Hampton Main Beach
Often featured on lists of the beach beaches in America, East Hampton’s Main Beach is a popular spot during the summer season. Like Cooper’s Beach, it has pristine white sand and a decent crowd. Parking can be a challenge, so it’s recommended to arrive early in the day or catch an Uber.
Ditch Plains Beach
Located in Montauk, Ditch Plains Beach is considered one of the best spots for surfing. The currents can become quite strong, so you’ll see a lot of lifeguards on the shoreline.
Cupsogue Beach County Park
Slightly more removed, Cupsogue Beach County Park tends to draw older crowds that want the beach without the scene. Many have caught on, so you’ll still need to arrive early to secure a carpark.