An Insider's Guide To The Hamptons
sailboat
Like Malibu or the French Riviera, the Hamptons is more of a state of mind than a zip code. The towns practically drip with perfection—from the quaint streets to the picture-perfect houses and manicured hedgerows—everything looks like it belongs exactly where it is.
In the Hamptons you don’t visit a town, you spend time in a village—even the names of which seem fancy: Amagansett, Sagaponack, Wainscott.
But for all its regalia and reputation, the Hamptons is, at the end of the day, a place like any other—one that is made up of locals and tourists, store owners and shoppers, corner delis and world-class bistros. And in the fall, after the tourists pack up and before the store fronts quiet down for the off season, it’s one of our favorite places to be.
Hamptons 101: The Towns
Sag Harbor sign

Sag Harbor

As the name implies, the heartbeat of Sag Harbor is, well, the harbor. Unlike its neighbors to the south, Sag Harbor Village is intimately tied to the waterfront—once a working port of nearby Gardiner’s Bay, Sag has been bustling with activity since the region’s top employer was the whaling industry. Rich in history and postcard-perfect views, this is a must-visit destination.
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house in Southampton

Southampton

Marking the entrance to “The Hamptons” and the South Fork of Long Island, Southampton is one of the two main towns in the Hamptons. Consisting of a collection of picturesque villages and hamlets, Southampton is the definition of over-the-top luxury. Stroll the streets downtown, visit a farmer’s market or two, and take in the breathtaking views of the ocean—Southampton is truly an idyllic destination.
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windmill in East Hampton

East Hampton

Making up the eastern end of the South Fork, East Hampton is the other major “town” in the Hamptons. East Hampton played a major part in early American settlement, was a hub of the whaling industry and was home to the influential Montaukett Native Americans—and this history is evident almost everywhere you go. From the posh streets of Amagansett to the open dunes and rugged beaches of Montauk, East Hampton has something for everyone.
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What To Do
beach shore

Hit The Beach

Even in the offseason, enjoying a day at one of the Hamptons’ renowned beaches is worth the trip. For visitors on the ocean side, Coopers Beach is a family-friendly spot to dig your toes into the sand, while those on the bay side will want to check out Havens Beach for the views of the Peconic River and Sag Harbor Bay.

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tube float on boat

Get On The Water

The best place to take in the scenic beauty of the Long Island coastline is from the water. And while there are plenty of charters to choose from, one of our favorites is the Kelpie, a 78-foot schooner, originally built in 1928, helmed by our good friend Shannon Carleton. The sunset sails are an absolute bucket list activity.

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couple next to a Jeep

Invite Your Friends

You don’t need to be a celebrity to enjoy the Hamptons legendary party scene. In fact, hosting your own get-together with friends and family is often the social event of the season. (If you’re looking for a little help with your next seaside fête, we recommend top-notch catering and party planning company Hamptons Aristocrat—you won’t be disappointed.)

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Where To Eat & Drink
Pierre’s owner

Pierre’s

With its iconic awnings and outdoor seating—and its fantastic food—Pierre’s brings the vibes of a Parisian bistro to Bridgehampton. Under the watchful eye (and friendly smile) of restaurateur Pierre Webber, Pierre’s is a great place for lunch, for a cocktail, or just for watching the scene. pierresbridgehampton.com

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Wölffer Estate Vineyard

Wölffer Estate Vineyard

There is no shortage of vineyards in the Hamptons, but one of our favorites to visit is Wölffer Estate Vineyard. The grounds are stunning, the wine is amazing, and there’s always something fun going on during the fall. wolffer.com

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Sag Harbor Pizza neon light sign

Sag Harbor Pizza

Sag Harbor Pizza is proof that not everything in the Hamptons is fancy, but it’s all really good. Sag Harbor Pizza is small, old school and delicious. If you’re looking for a no-brainer meal, check it out. sagpizza.com

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Kerber’s Farm 'Home' sign

Kerber’s Farm

Technically speaking Kerber’s Farm is not in the Hamptons. It’s located in Huntington, New York. But, it’s so beautiful and happy, full of delicious food and brimming with community love, it’s a must-stop if you’re going to, or heading home from, the Hamptons. Restored and run by our good friend Nick Voulgaris, Kerber’s is a must-visit if you’re in (or near) the area. kerbersfarm.com

Where To stay
The American Hotel front

The American Hotel

Situated along Sag Harbor’s historic Main Street and just a short walk from the town’s picturesque wharf, the American Hotel seamlessly blends historic charm and modern comforts. Built in 1846 as a trading post and boarding house for the whaling industry, the American— now featuring eight guest rooms, a fine dining restaurant and some of the best cocktails in town—continues to build on its legacy as a welcoming space for all members of the community to meet. theamericanhotel.com

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Baron’s Cove sign

Baron’s Cove

With gorgeous harbor views, top-notch amenities and local ties dating back to the 1950s, Baron’s Cove offers a best-in-class resort atmosphere paired with a real slice of Sag Harbor life. The saltwater pool, luxuriously appointed rooms and interior decor are all tributes to the area’s nautical past. Stop in for a drink with friends at the hotel lounge then head outside onto the deck to take in the sunset. caperesorts.com/barons-cove

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Room At The Beach sign

Room At The Beach

Heading eastbound on the Montauk Highway, right past Bridgehampton, you might spot what appears to be a classic roadside motel on your left. Upon closer inspection, you’ll find that Room At The Beach is anything but average. Fully restored and reimagined, the 10 guest rooms, pool and beautifully manicured grounds and garden offer guests a serene homebase for their Hamptons getaway. Iwantaroomatthebeach.com

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The 1708 House

The 1708 House

Within walking distance of Southampton’s quaint shops, restaurants and galleries, the 1708 House is one of the most unique stays in the area. As the name suggests, the house dates back to 1708, but it’s fully restored to offer guests a welcoming, memorable experience. After enjoying breakfast, head out on bikes to spend the day at Coopers Beach or set off on an adventure to the area’s many points of interest.
1708house.com