The Hamptons: Your All-Inclusive Guide

by Samantha Leal Jul 2019 Also on Digital Edition

The Hamptons, located on the South Fork of Long Island, are a respite for many New Yorkers in the summertime (and beyond). But each area has a distinct identity—perfect for when you're deciding between a social vacation or a true escape from it all. So, where do you begin? We've got you covered.

But before you go, you should know that the Hamptons are extremely popular in the summer—if that wasn't apparent. Many families and groups from the city have timeshares or summer rentals in homes spread across the area, so hotel lodging is sparse and can get expensive. Airbnbs can be your friend here, but only if booking with plenty of time before your visit or as a last-minute stay. (Oh, and make sure to check the address—some hosts will fudge the location a little to be in a more prime spot.) If you're not looking for a prime-time beach getaway, you might think of going a little off-season in September, when the water is still warm but the crowds are much less. However, some restaurants and hotels are only seasonal, so double check before choosing when to book the trip.

Amagansett

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THE VIBE

Technically part of East Hampton, this hamlet has an even more laid-back vibe than its big sister and is located between the main part of East Hampton and Montauk. It's the perfect midway point between the two—great for exploring both—and offers a scenic and quiet escape.

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WHERE TO STAY

Your best bet for staying in Amagansett is at hotels and inns throughout East Hampton, but Amagansett has a handful of resorts and B&Bs that can be booked well in advance of your stay. The Gansett Green Manor is beautiful and pristine but hosts a lot of weddings, so double-check your stay.

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WHERE TO EAT

Wölffer Kitchen Amagansett is the second eatery in the Hamptons from the team at Wölffer Estate Vineyard in Sagaponack/Southampton. (Note: All Wölffer venues have a strict no big group or bachelor/bachelorette party policy.) It's got a full wine list (obviously) and great eats for any time of the day, plus an outside patio and backyard lounge seating. La Fondita is a must for Mexican food, and you can't miss the Hampton Chutney Co.—a true Amagansett establishment—with amazing dosas.

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WHAT TO DO

The beaches: You have Indian Wells, which is a local favorite, and Atlantic Avenue Beach, which attracts pretty much everyone from the area. The Stephen Talkhouse is a great spot to watch live music in an old home and is a true East Hampton icon.

Bridgehampton

THE VIBE

Bridgehampton is quintessential Hamptons, mixing historic homes and upscale dining with casual eats and quaint beaches. You'll get a taste of everything here, whether you're looking for an easy summer getaway or something a little more luxe.

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WHERE TO STAY

Topping Rose House is a luxury hotel featuring a restaurant by Jean-Georges Vongerichten. It's picturesque, with 16 guest rooms and six suites, a pool and a spa. It's within walking distance to cafés, art galleries and more—plus, it features a Land Rover shuttle to take you to the beaches or other attractions nearby.

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WHERE TO EAT

We weren't kidding about Topping Rose House's restaurant, operated by Vongerichten (after taking over from Tom Colicchio in 2016). It's a farm-to-table restaurant with much of the produce grown on the premises. Almond is another local favorite, with locally sourced food and a menu that changes with the season. Bobby Van's is always a solid choice for a great steak. Head to Elaia Estiatorio for a Greek feast that will leave you happy and full on hummus. Candy Kitchen is a mainstay, cash-only diner (nothing fancy here) that serves some of the best homemade ice cream.

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WHAT TO DO

The Polo Match & Cocktail Party is held in Bridgehampton, while the Hampton Classic Horse Show takes place here every August. A trip to Channing Daughters Winery is great for tasting some local wine. Lastly, and obviously, the beach calls.

East Hampton

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THE VIBE

East Hampton has more of a laid-back, artsy vibe with plenty of charm and good eats. Here, you might see a celebrity (or three), and you'll have your pick of pristine beaches.

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WHERE TO STAY

The Maidstone Hotel is a boutique hotel that features 16 rooms and three cottages with their own private parking areas, private entrances, gardens and fireplaces. You can also book a room at Mill House Inn, a luxury getaway with only 10 rooms and truly unparalleled service.

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WHERE TO EAT

Babette's and Serafina are long-time classics for lazy lunches. Sam's is the choice for a great pizza pie, and Bostwick's Chowder House offers amazing seafood and chill vibes. Nick & Toni's is another long-running institution—a true go-to serving East Hampton crowds since 1988.

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WHAT TO DO

Check out the events happening at Guild Hall to catch a screening, exhibition, panel or reading. Make sure to stop by and walk the paint-splattered floor at the Pollock-Krasner House and Study Center, a studio and gallery in the home Jackson Pollock shared in the '50s with his wife, artist Lee Krasner. Ready for the beach? Main Beach is the closest to downtown East Hampton, about a 25-minute walk. (There's also a free shuttle.) It's one of the most popular beaches for exactly this reason.

Montauk

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THE VIBE

Montauk is located at the tip of the South Fork, or as many say, at “The End of the World.” In recent years, it has gone from a fisherman's village to the place to see and be seen for young city-dwellers looking for a social escape. From day dance parties at The Surf Lodge to sunbathing at Gurney's Montauk, it's definitely a summer scene.

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WHERE TO STAY

There are many options in Montauk, depending on your agenda. The Surf Lodge is an option for those who want to be a part of the action, while Gurney's Montauk is the only year-round resort in the area. Gurney's also has a new property that just opened, Gurney's Star Island Resort and Marina, which takes over the Montauk Yacht Club Resort and Marina. After a $13 million renovation in just a year, the resort has a more laid-back vibe than the original Gurney's Montauk. There's also Ruschmeyers, another place where the environment changes at night, but it's basically a camp for adults—with adorable cabins, a teepee, an outdoor bar and picnic tables.

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WHERE TO EAT

There are so many places to eat in Montauk, it's hard to narrow it down. The waterfront Crow's Nest is a rustic-chic restaurant (and hotel!) that will not disappoint. Gurney's Star Island Resort and Marina offers three new restaurants for the area helmed by executive chef Jeremy Blutstein, a James Beard-award nominated chef who most recently ran Almond in Bridgehampton. Il Forno has pizzas and Italian fare, while The Pool Club features (you guessed it) traditional summertime fare, including sriracha lobster rolls and fish tacos. Showfish is the seafood restaurant that has everyone talking. The OG Gurney's features Scarpetta Beach, the sister restaurant of the iconic Manhattan eatery. For Mexican fare, head to The Hideaway, a local favorite that's not touristy at all. John's Drive-In is a must for ice cream. Just go.

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WHAT TO DO

You have to see the Montauk Lighthouse, which was completed in 1796 and is the oldest lighthouse in New York state. Climb the 137 steps to the top to see Block Island Sound, the Atlantic Ocean and beyond. Grab a beer at Montauk Brewing Company, and stroll downtown to check out art fairs and little shops before heading to the beach. Go to Surf Lodge for a scene, including the annual summer concert series.

Sag Harbor

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THE VIBE

Sag Harbor is an idyllic village with an iconic windmill and old-school appeal. It feels like a year-round village where people actually live, and they do—giving it more of a homey feel than some of the other villages and hamlets. It's located on Gardiner's Bay and has a rich whaling history.

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WHERE TO STAY

The American Hotel has been a constant on Main Street since the '70s, though the structure dates back to the 1800s. You can't miss the brick building, and its charm is a nod to the village overall.

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WHERE TO EAT

The restaurant at The American Hotel is top-notch, while the original Tutto il Giorno is also a prime pick. Page at 63 Main features locally sourced American dishes, and Lulu Kitchen & Bar is a fixture on Main Street for good reason. Start your day with a doughnut and coffee from Grindstone Coffee & Donuts, founded by Kyle Shanahan whose stepfather is chef Michael Symon. (Just make sure you get there early—they sell out fast.) Then later grab a burger and a milkshake at LT Burger. The Beacon is another amazing spot, perfect for a more upscale dinner—and great sunset views.

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WHAT TO DO

A trip to the iconic windmill is a given, located at the foot of Main Street near the Long Wharf. Learn all about the history of the town and its connection to whaling at the Sag Harbor Whaling & Historical Museum. Across the street you can check out the Custom House, a museum that focuses on the early history of the United States. Lastly, see a play, comedy show or performance at the Bay Street Theater & Sag Harbor Center for the Arts.

Southampton

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THE VIBE

Southampton is the village of affluence. It's a mecca of shopping and celebrity, and it has an old-money vibe that translates to grand mansions, immaculately manicured lawns and unspoiled beaches. Here you'll find antique shopping, polo matches and more. Make sure to check out Main Street for shopping and restaurants, while Gin Lane features some of the aforementioned mansions.

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WHERE TO STAY

Southampton Inn is a great pick, located in the heart of the village and in walking distance (literally steps) to Main Street. It has 90 guest rooms, a pool, tennis court, and yes, you can bring your pets. Looking to re-center yourself? Shou Sugi Ban House just opened in the hamlet of Water Mill, part of Southampton, and is a wellness program, spa and retreat made up of 13 rooms located on 3 acres.

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WHERE TO EAT

75 Main is a mainstay (pun fully intended), for Italian fare since 2010. Tutto il Giorno is a chic, Italian restaurant (not surprising—it's Gabby Karan de Felice's spot, daughter of Donna Karan) with a patio that becomes a social haven for Southampton-stayers. (The original and other location is in Sag Harbor.)

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WHAT TO DO

Attend a polo match at the Southampton Hunt & Polo Club, or peruse the boutiques on Main Street. Head to Water Mill and check out the Parrish Art Museum, which focuses on works from the artist colony of the South Shore and North Shore. Right next to the museum is the South Fork location of Duck Walk Vineyards, where you can taste wines among 30 acres of grape vines.


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