I’ve driven through countless times — Amagansett — the last Hamptons town before Montauk, “The End” as locals call it. But I never stopped, save for a quick lobster roll at Lunch, the roadside spot long known to locals and officially made famous in Showtime’s The Affair. Despite Amagansett’s picturesque downtown, replete with cedar-shake boutiques, NYC-outpost restaurants, white-sand beaches, and blooming-in-summer hydrangea, I have never properly visited.
But this time is different. This time, I intentionally design a stay in Amagansett. Like many Hamptons towns, Amagansett’s hotel scene is limited. Most visitors stay in their own homes — or their friends’ — many of them high-profile names. Paul McCartney, Sarah Jessica Parker and Matthew Broderick, Gwyneth Paltrow, Jerry Seinfeld, and Billy Joel are among those who own homes or visit frequently. But after hearing about Amagansett’s The Roundtree — a member of the Small Luxury Hotels of the World — I decided to spend a few shoulder-season days exploring the coastal town’s quietly emerging luxe hotel scene.
Checking in, Slowing Down
Although the famed Hampton Jitney (that runs from Manhattan) stops directly in front of The Roundtree, I choose to drive — a relaxing-enough experience in the off season. But within an hour of my arrival to the two-acre, 14-room property spread across renovated cottages and centuries-old barns, it is clear I do not need a car. Complimentary bicycles are available to ride at whim; ‘downtown’ is literally right down the street, and one of the most known farmers markets, Amber Waves, is just a block away. Popping inside the vibey market, amidst wildflower bouquets and artisanal cheeses, I spot ‘Summer in a Bottle,’ a 2024 rosé produced at nearby Wolffer Estate in Sagaponack. But later, as I settle onto my private outdoor terrace to watch the sky turn from blue to sunset pink, I realize a wine purchase isn’t necessary. Staying here is like overnighting in a close friend’s home.
“White or rosé?”
Inside the hotel’s intimate reception cottage, a bottle of white — or rosé instead — chills on ice, alongside savory snacks, jars of homemade cookies, and colorful coffee table books, many with narratives of Southampton, Bridgehampton, Sagaponack, and Montauk. The wine and nibbles are there for the taking, as are the neatly wrapped brown paper bags of chocolate bars, marshmallows, and graham crackers (complete with sticks for s’more making) discreetly positioned by the various fire pits scattered around the great lawn.
Low-Key Luxury, Old-Hamptons Style
While luxurious amenities continue to reveal inside my two-bedroom cottage: Frette linens, Grown Alchemist bath products, and minibar pre-stocked with sparkling water, fresh fruit, and a few surprises like locally made South Fork Bakery brownies, the vibe is low key. Couples stroll hand in hand to town; others take bikes to the beach or to dinner at nearby Il Buco al Mare. A dog rests at the feet of its person (a few cottages are designated dog friendly) in front of a fire pit, while friends converse over wine at tables on the lawn.
Journalist Dan Rattiner, who has lived in the Hamptons most of his adult life, once wrote that “Nobody just winds up here by accident while drifting through to somewhere else. We stick out into the sea. You have to decide to come to the Hamptons. It’s a decision.”
Each Hamptons town is said to have its own personality and story. Where Southampton is high glam and tastefully flashy, Bridgehampton covets designer stores, rolling vineyards, and horses. And where Sag Harbor is nautical, a former whaling colony, and forever artistic (writers, especially, come here), Amagansett is quiet and discreet, with emphasis on natural beauty, mid-century modernism, and the sea.
From Whalers to Weekenders
Certainly, with street names like Ship Wreck, Atlantic, and Surf Drive, there’s no denying Amagansett’s deeply rooted maritime connection. The weathered cedar-shake Marine Museum, overlooking the ocean on Bluff Road, tells the tales of whalers and fishermen, while even the beaches come with their own whispering narratives. Atlantic Beach, where I walked every morning during my stay, was reportedly where four German spies were dropped off by submarine (during WWII). Indian Wells — now a family-friendly stretch dotted with dunes and food trucks selling açaí bowls — was known in the 1970s as “Asparagus Beach,” a playful nod to the clusters of singles who stood like asparagus stalks on the lookout in hopes of finding a date.
The Hamptons’ first settlers, sent by the King of England, arrived in 1640 (on a sailboat from Massachusetts), laying the foundation for today’s seven white-steepled villages and sprawling farmland — much of it once devoted to potatoes. But it was the arrival of the railroad in the 1800s that brought New York City’s elite. Whitneys, Woolworths, Dukes, Fords, Hearsts, Vanderbilts, Hiltons, and Rockefellers were among those who built grand, 10-bedroom beachfront cottages, launching a legacy of summering in the Hamptons. Each spring, cottage owners were given a “Blue Book” filled with the names, addresses, and phone numbers of fellow home owners, along with their children’s names and the Ivy League universities they attended. Writers — Arthur Miller, John Steinbeck, Truman Capote — and artists William de Kooning, Jackson Pollack, Roy Lichenstein, and Andy Warhol soon followed.
Today, newly built mansions fuse with the original sprawling cottages — now known as Devon Colony — along with those built in the 1960s and 70s as part of the Amagansett modernism movement. While not a formal architectural style, the Amagansett movement embraces the key principles of California modernism most often seen in Palm Springs (open floor plan, clean lines, minimalist aesthetic) with the unique character of the Amagansett sea-and-dune landscape. Architects Norman Jaffe, Paul Rudolph, and Richard Meier were among those closely linked to the movement; their materials of choice: glass, steel, wood, and concrete.
Neil Simon Slept Here
Although not considered part of the Amagansett modernism movement (due to its traditional mid-century shingle style), Beach House — found in the prestigious Amagansett Dunes neighborhood (and The Roundtree’s most luxurious accommodation) — offers insight into the area’s modern design concept. Built in the 1960s by renowned East Hampton architect Alfred Scheffer, the house was originally owned by Tony Award-winning playwright, Neil Simon (best known for the Odd Couple).
Now part of The Roundtree, the recently renovated bungalow — close to both the ocean and hotel — features three bedrooms and spa-like bathrooms, a wood-burning fireplace, gourmet kitchen, and a separate, two-story guest cottage. The house, which can be rented for the entire summer, also comes with a personal concierge and most recently, access to the hotel’s newly launched personal chef-in-residence experience.
Bali Meets the Hamptons
There is no formal restaurant at The Roundtree although a complimentary continual breakfast with pastries by nearby Il Buco, is served daily. But with the recent arrival of French-trained, Bali-born Chef Dewa Wijaya, Roundtree guests are now privy to a new menu of wellness-centric a la carte items.
No stranger to luxury hotels (or wellness), Chef Wijaya perfected his craft at COMO Shambhala Estate (Bali) where he led the acclaimed Glow restaurant and Kudus House — overseeing the culinary experiences for noted public figures, celebrities, and global gastro travelers. He also developed wellness-driven dining programs across COMO’s properties, and created the popular “Taste of COMO” culinary pop ups.
“Chef’s philosophy aligns perfectly with our vision of understated luxury and personalized wellness,” says Roundtree owner Sylvia Wong. “We’re excited to offer our guests something truly original — a nourishing, immersive culinary experience that reflects the spirit of this place.”
For Chef Wijaya, The Roundtree, which he describes as “an incredibly special place: peaceful, intentional, and deeply personal,” offers the perfect synergy. “I was drawn to the idea of creating transformative culinary experiences without the structure of a traditional restaurant,” he says. “It allows for a deeper connection to guests and to Long Island’s rich and diverse bounty of produce and ingredients.”
In addition to his wellness menu, Chef works one on one with guests to personalize meal planning throughout their stay — be it solo dining or relaxed, family-style dinners under the stars — and leads hands-on cooking demonstrations and intimate classes highlighting the connection between mindfulness and meal preparation. Even non guests can tap into Chef Wijaya’s expertise by bringing his culinary consultations and private chef services into their private Hamptons (or even New York City) homes.
While my stay at The Roundtree sadly pre-empted Chef Wijaya’s arrival, I have long been a fan of COMO Hotels & Resorts — especially COMO Parrot Cay (Turks and Caicos) and COMO Shambhala (Bali), where I’ve spent transformative wellness time. Now, in Amagansett, the thought of pairing Chef’s healthful cuisine with morning yoga, daily beach walks, bike rides, and nights under starry skies — coupled with my newfound fascination for Amagansett modernism — makes me never want to pass through again.
But to stay.
Feature image, courtesy of The Round Tree.
