The Hamptons are, of course, synonymous with summer. A destination long frequented by New Yorkers who want a thriving food scene, fashion, and a few familiar faces—but with a beachy backdrop. It’s New York’s most storied summer escape, made iconic by residents like Jackie Kennedy, Truman Capote, Lee Radziwill, and Gloria Vanderbilt, and still a magnet for artists, editors, designers, and well-heeled vacationers who treat summering out East as something closer to a ritual than a vacation.
By August, the pace doesn’t slow—it intensifies. There’s a final push to savor it all: every golden-hour dinner, every farmers’ market haul, every salty swim and post-beach glass of wine. Tables are still fully booked, the boutiques still bustling, and everyone is chasing that one last weekend that might just be the best of the season.
While new shops and pop-ups debut each season, the heart of the Hamptons remains unchanged—quietly appreciated by those who skip the scene and return for the unflashy, unforgettable places they’ve known for years.
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To do it right, you need more than a map—you need a few names whispered over dinner. The trusted haunts, the just-opened gems, the stylish pit stops worth pulling off for on the way in or out (because, let’s face it, the traffic rarely shows mercy) to grab a linen set or a last-minute hostess gift before the final stretch east. Around here, word-of-mouth is everything—and knowing where to go makes all the difference between a good weekend and a great one.
The Hamptons may sprawl across towns and beaches, but those who return year after year know: where you stay shapes how you experience it. From low-key motels in Montauk to designer-drenched guest houses in Bridgehampton, there’s no shortage of places to hang your hat. But for a stay that’s quietly elegant, grounded, and central to it all, The Maidstone is the perennial favorite.
Tucked into East Hampton’s historic district, the hotel has been a fixture on the East End for more than 150 years—and while the interiors have been thoughtfully refreshed, it hasn’t lost its soul. Morning coffee in the garden feels like something out of a Slim Aarons photo, and its 19 guest rooms—done in sandy neutrals, warm ambers, and soft peaches—channel the kind of effortless coastal calm that defines the region. From here, you can walk to town, bike to the beach, or hit 27 to explore the rest of the South Fork without ever feeling too far from home base.
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The Hamptons isn’t a place that demands an itinerary; it encourages the opposite. Long breakfasts, beachy afternoons, and unplanned stops at flower stands or wineries are part of the rhythm. Still, a little foresight goes a long way, especially when it comes to arrival and departure. Weekend traffic has its own agenda, and the savviest travelers know to turn the drive into part of the experience. That might mean timing your trip around a smart pit stop. Just off the highway, Belmont Park Village has quietly become a go-to among in-the-know travelers. The open-air luxury outlet is a welcome surprise on the way to—or from—the South Fork, especially if you’re in the mood to pick up something new for the weekend. A Missoni set, for instance, that works just as well for a day on the beach as it does for dinner later. Or a classic Brunello Cucinelli linen shirt. With stores like Valentino, Vivienne Westwood, and Thom Browne, plus good food (a rarity on the Long Island Expressway), it’s the kind of stop that you look forward to and makes the weekend feel like it’s already started—and hopefully, a well-timed shopping stop that pays off in the form of the perfect summer bag.
Once you’ve made it out East, start the day with a visit to Carissa’s, then head to Main Beach before the crowds arrive. Spend an hour or two wandering Main Street in East Hampton, where Prada, Loewe, Gucci, and Rolex blend into white-shingled storefronts showcasing the newest summer collections. Tenet Shop offers a carefully curated edit, and The Monogram Shop is always a good choice for a cheeky gift or a custom beach towel. If you’re in the mood for culture, a trip to the Pollock-Krasner House and Study Center in East Hampton offers a rare, intimate look at the former home and studio of Jackson Pollock and Lee Krasner—complete with splattered floors that still bear the marks of mid-century masterpieces. For something slower, book a few hours at Shou Sugi Ban House in Water Mill, a wellness retreat offering holistic spa treatments in a serene, cedar-scented setting. Or if you prefer ocean views with your deep tissue massage, the spa at Gurney’s in Montauk remains a classic. The trick is not to do too much. The Hamptons rewards the unhurried—whether you’re spending the weekend on the sand, in a sauna, or just stretching the drive home a little longer.
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When it comes to eating and drinking in the Hamptons, it’s all about knowing where to go—and when. Lunch at Duryea’s in Montauk is a must: order the oysters and the viral lobster cobb salad as yachts drift by and the breeze rolls in off the harbor. It’s a see-and-be-seen spot, yes, but the view alone is worth it—and your Missoni beach set won’t be out of place. For dinner, LDV at The Maidstone offers a romantic garden setting surrounded by blooming hydrangeas. The menu leans Italian with a coastal spin: burrata, gnocchi with clams, and market-fresh seafood served with just the right amount of ceremony. And no visit is complete without a reservation at Nick & Toni’s, the East Hampton institution where fried zucchini, their signature romaine salad, roasted chicken, and steak are as essential to summer as SPF and a nice glass of rosé,
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