This Gorgeous Coastal Region of New York Has Incredible Restaurants and Hotels, a Thriving Arts Scene, and Beaches Worth Visiting in Any Season

How to plan the perfect trip to New York's Hamptons in any season.

The Hamptons. The East End. Out East. No matter what you call it, this stretch of beatific bay and ocean coastline between Southampton’s Shinnecock Canal and – depending how you look at it — the outer reaches of Montauk has long been favored by the well-heeled and the well-off.

But you don’t have to be among the one-percent to enjoy eastern Long Island’s pristine beaches, thoughtful restaurants, art museums, and shopping destinations. Home to the yearly Montauk Music Festival, the critically acclaimed Hamptons International Film Festival, and numerous local wineries, including the increasingly popular Channing Daughters Winery and Wölffer Estate Vineyard, the Hamptons is far more than a place to see and be seen. It’s a place to relax, to savor, and to take in the art, beauty, and surroundings of one of New York’s most bucolic collections of communities.

Read on for the ultimate guide to planning the perfect Hamptons vacation — including when to visit, where to stay, and what to do.

Best Hotels & Resorts

Crow's Nest

Few properties offer a more compelling stay than Montauk's Crow's Nest, where bohemian decor, twinkling Edison bulbs, and a view of Lake Montauk at sunset are just part of hotelier Sean MacPherson's surf-centric vision. The hotel's mix of rooms and cottages runs adjacent to its much-beloved Mediterranean-style restaurant, which is always booming from May through September.

Roundtree

Farther west, at the 15-key Roundtree, in Amagansett, guests can explore the boutique property alone or with a furry friend (the hotel is pet-friendly). Beach bonfires, cooking classes, trips to local wineries, and guided walking tours are all signature experiences offered for a bespoke Hamptons getaway.

Marram Montauk

The 96-room Marram Montauk is a bohemian paradise, with a pool overlooking Atlantic Terrace beach (a surfing spot with a notoriously fun break). Guests are free to dine at the in-house restaurant, Mostrador Marram, with its beachy, outdoor vibe; lounge overlooking the ocean; take one of the hotel’s creative workshops; or grab a complimentary bike for a ride into town.

Baron's Cove

In Sag Harbor, the 67-room Baron's Cove offers guests a resort experience, with upscale amenities like a pool and on-site restaurant and an incomparable view of the water. Open year-round, there's not a bad time to visit the property, which boasts a cozy dining room and fireplace.

Shou Sugi Ban House

A wellness retreat just off of the highway in Watermill, Shou Sugi Ban House offers guests holistic wellness programming in 13 guest studios. Visitors have access to a spa with hydrotherapy pools, a roof deck, fitness center, organic vegetable garden, library, and healing arts barn. Meals are plant-based, but expertly created.

Best Things to Do

Stroll through the perfectly manicured gardens at Sagaponack's Madoo Conservancy. Established in 1967 by artist, writer, and gardener Robert Dash, this stunning space is like stepping into a fantasy dreamscape.

Head over to Bridgehampton's Scuttle Hole Road for Channing Daughters Winery's seated tastings (reservations are recommended). You can even make a whole day of it, stopping by Wölffer Estate Vineyard, in neighboring Sagaponack, for a glass of the winery's esteemed rosé, followed by a digestif at the South Fork's very own Sagaponack Farm Distillery.

As Victoria M. Walker reports in the August 2023 issue of Travel + Leisure, the Southampton African American Museum is a de rigueur destination for those seeking a comprehensive understanding of both Black life in the Hamptons and “Black culture in general.” “The museum,” she writes, “is dedicated to preserving the African-American story on Long Island through exhibits such as ‘Grooming a Generation,’ a poignant look at the history of Black hair salons in the region.”

Best Shopping

Walker recommends Blue One, in Bridgehampton, a boutique founded in 2007 by Jarret Willis and Crystal Smith Willis. “The shop’s fashionable wares run the gamut from dresses by Ulla Johnson and Jonathan Simkhai to blazers and denim from the avant-garde label Ser-o-ya,” Walker writes in the August 2023 issue of the magazine.

Sag Harbor’s Thriftknd, owned by Brittany Rivkind, offers up vintage and pre-owned clothing and accessories, as well as other ephemera that is typically hard-to-find in the tony Hamptons. Find everything from pre-loved denim to cute hair clips at this curated and playful Sag Harbor boutique.

Southampton’s Hidden Gem, owned by Tanya Wilock and Temidra Wilock-Morsch, reflects, Walker says, the owners’ Antiguan heritage. “Along with their own line of jewelry and accessories, the duo sources art and apparel from artisans around the world,” Walker writes.

Best Restaurants

Sant Ambroeus

New to East Hampton – the original is a stalwart in Southampton – Sant Ambroeus is, says Joey Wölffer, Hamptons resident and daughter of vintner Christian Wölffer, “just impeccable,” with ambient lighting, gray and comfortable banquette seating, and easy-to-love pasta dishes. In the August 2023 issue of Travel + Leisure, she describes the restaurant as “always on point.”

Nick & Toni's

Those in search of an established haunt can head onto N. Main Street to Nick & Toni’s, which has been going strong for over 30 years (and where anyone can reliably run into a celebrity on a Saturday night in summer). If you can make it through the maitre’d, order any manner of the restaurant’s seasonally changing Italian specials, which reflect the East End’s bounty.

Beacon

David Loewenberg’s Sag Harbor restaurant with a view, Beacon, overlooks the water and offers one of the best sunsets in town. “People visiting the region always want to know where they can get the freshest fish and vegetables outside of a fishmonger or farmer’s market, and I think this is the place,” Wölffer says. Beacon remains open through Indigenous Peoples’ Weekend each year. 

Lulu Kitchen & Bar

Lulu Kitchen & Bar, a wood-fired-centric restaurant in downtown Sag Harbor, offers some of the coziest environs for dining in the Hamptons. Bistro-style fare like steak tartare, ice-cold towers of oysters and top neck clams, and the restaurant’s signature cauliflower, arrive in a room that smells of wood smoke and expertly crafted martinis.

1770 House

It’s hard to outdo 1770 House, in East Hampton, with its hand-hewn beams and working fireplaces. “This historic house in East Hampton really did open as an inn in 1770,” Wölffer says. “I always go in the fall and winter, when the fireplace keeps things toasty.” The spicy Montauk fluke tartare, served with wasabi tobiko, is a classic, as is the roasted natural chicken, with maitake mushrooms and a Channing Daughters Ramato jus.

Best Time to Visit

Although the Hamptons is divine in its high season (summer), don't discount Long Island's South Fork during its less popular periods. May and September — two months often referred to as the shoulder season — are great times to visit this New York area. Prices are lower, crowds are thinner, and many restaurants are already (or still) open. Plus, because the Hamptons is insulated on all sides, the temperature is a bit warmer than it typically is in New York City, meaning beach weather arrives a few weeks earlier and lingers a few weeks later.

In May, Montauk hosts the Montauk Music Festival, and in October, the Hamptons hosts the Hamptons International Film Festival, two major events that are worth heading into town for. So, don't feel confined to June, July, and August when making your vacation plans. The best time to visit the Hamptons is before the crowds descend and right after they leave.

How to Get There

Montauk and East Hampton are both equipped with private airports, but the closest major airport is about an hour west, in Islip, New York. If you don’t intend to travel to the Hamptons by car, you can take the Hampton Jitney, which connects the Hamptons to New York City with hourly stops in-season through nearly every hamlet (the schedule changes in the off-season).

The Long Island Railroad, connecting New York’s Penn Station to Long Island, operates a handful of trains between Montauk and the city daily. These trains also stop in Southampton, East Bridgehampton, East Hampton, and Amagansett. The trip between Montauk and the city takes about three hours.

Neighborhoods to Visit

During your stay, walk around the hamlet of Sag Harbor, an old whaling village that was established in the early 1700s. Antique stores, charming traditional homes, and bayside charm permeate this traditional enclave. In Sag Harbor, Foster Memorial Beach (otherwise known as Long Beach) is ideal for those who prefer to swim in shallow, calm waters or like a little less of a hike from the sand. It's also open to the public.

Other hamlets with walkable centers include Southampton, East Hampton, Bridgehampton, Amagansett, and Montauk. You can find plenty to do in these villages, from shopping to dining to just walking around.

How to Get Around

Although you can hire an Uber to get from hamlet to hamlet – and although some properties do provide bicycles that you can borrow free of charge – the best way to get around the Hamptons is by car. There is no uniform public transportation currently available on the East End of Long Island. If you do not own a car, you might consider renting one before arriving on the East End, as rental options are slim.

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