The Hamptons,
New York:
Before & After.
“We were at Westhampton Beach in the early teens — boating, swimming, eating well, relaxed in a way the Hamptons has largely forgotten how to be. We came back as young adults living in Manhattan and took the train out to Southampton. The beaches were still extraordinary. They still are. The Hamptons is worth knowing despite everything it became — you just need to know how to find the version that still matters.”
In this guide
01 — Before & after
The Hamptons we knew.
The Hamptons that exists now.
The Hamptons in the early 1970s and 1980s was a collection of beautiful Long Island beach towns that happened to be where wealthy New Yorkers went in summer. The beaches were extraordinary — wide, clean, Atlantic-facing, the best ocean swimming within reach of the city. The towns were charming. The restaurants were good. The whole thing was relaxed in a way that didn’t require explaining or defending.
We went as teenagers — boating, swimming, eating well, the children of parents whose New York friends had the connection. Westhampton Beach specifically, the westernmost of the Hamptons towns and the closest to the city. Down to earth. Nothing flashy about it. A beach club, a boat, the ocean, and the kind of summer that doesn’t need to be documented to be remembered.
The Hamptons — 1970s & 80s
Beach clubs, boating, relaxed summers. The Hamptons before it became a brand. Westhampton Beach specifically — the closest, the least flashy, the most genuine of the group.
A train or bus from the city. Not a helicopter. Not a $3,000 summer pass. Just the LIRR and the beach at the end of it.
The beauty was already there. The production hadn’t arrived yet.
The Hamptons — now
$595 helicopter seats. $50,000 weekly rentals. Celebrity sightings in July. A “Hamptons aesthetic” that gets licensed to everything.
Also: still the same extraordinary beaches. Still the same Atlantic. Still the best ocean swimming within reach of New York City. The bones are unchanged.
Worth knowing despite what it became — if you know how to navigate it.
“The Hamptons didn’t ruin its beaches when it became famous. The beaches were always that good. The question is whether you can get to them without the production getting in the way.”
We also came back as young adults living in Manhattan — taking the train out to Southampton, staying in a rental house with friends, experiencing the Hamptons through clear and present eyes. The beaches held up. Southampton in the off-season especially — quieter, more honest, the summer crowd gone and the town returning to itself. That version of the Hamptons is still there. This guide is partly about finding it.
02 — The towns
Eight towns.
Very different from each other.
The Hamptons is not one place. It’s a string of towns along the South Fork of Long Island, each with a distinct personality, price point, and crowd. Understanding which town fits which kind of trip is the most useful thing this guide can tell you.
Our starting point
Westhampton Beach
The closest Hamptons town to NYC — 90 minutes by car, direct LIRR service. The most down-to-earth of the group. Real town, real beach, none of the East Hampton pretension. Where we started. Still the right call for most people.
Classic money
Southampton
Old money, beautiful estates, excellent beaches. The most traditional of the Hamptons towns. Main Street shopping, serious restaurants, the Parrish Art Museum. Where we returned as adults. The beaches are among the best on the East Coast.
The scene
East Hampton
The celebrity epicenter. Georgica Beach, Barefoot Contessa, the Main Street that makes New York magazine’s summer coverage every year. Beautiful and exhausting in equal measure in July. October is a different story.
The charmer
Sag Harbor
Former whaling village on the bay side. Independent bookstore, excellent restaurants, a Main Street that feels genuinely like a town rather than a summer performance. The most livable of the Hamptons villages.
The end of the road
Montauk
The easternmost point of Long Island. Surf culture, lighthouse, the Atlantic at its most dramatic. Less manicured than the other Hamptons towns — more honest, more elemental. Increasingly discovered but still has the edge that made it worth discovering.
Wine country
Bridgehampton
Wolffer Estate Vineyard is here — the most beautiful winery in the Hamptons. Polo fields, farmland, the surprising agricultural heart of a destination that forgets it’s built on farmland.
03 — Getting there
Take the train.
We always did. It still works.
The Hamptons traffic situation in 2026 is exactly as bad as you’ve heard. Summer Friday afternoons on the Long Island Expressway run 4.5 to 5 hours from midtown. Sunday afternoons heading back are worse. Driving to the Hamptons on a summer weekend is a choice that requires either genuine stoicism or a very good podcast collection.
The train was always the right answer and it remains the right answer. We took it from Manhattan in both eras — as teenagers with our parents’ friends and as adults living in the city — and the LIRR to the Hamptons is one of those rare New York experiences that is exactly as good as it should be.
The Cannonball — worth knowing about
The LIRR’s summer Friday express service to the Hamptons — nicknamed the Cannonball — runs from Penn Station with limited stops, reaching Southampton in about 2 hours and 45 minutes. It’s extremely popular and sells out. Book in advance through the MTA app. For the cost of a taxi to the airport you get a scenic two-hour train ride through Long Island and arrive at the Hamptons without having sat in traffic for five hours.
04 — Where to stay
Rent a house.
The Hamptons was built for it.
The Hamptons accommodation model has always been the rental house — large shingled properties with pools and beach access, rented by the week, shared among families and friend groups. Hotels exist in the Hamptons but they’re not why people come. The rental house is the experience.
We stayed in rental houses in both eras — as teenagers with our parents’ friends and as young adults from Manhattan. The house is what makes the trip work. The right house, in the right town, with the right people, is the whole Hamptons experience. Everything else is secondary.
The right answer for most people
Rental house — any town
A shingled house with a pool, walking distance to the beach, enough bedrooms for the whole group. This is how the Hamptons has always been done and it’s still the right call. VRBO has excellent inventory across all the Hampton towns — Westhampton for proximity, Southampton for beaches, East Hampton for scene, Montauk for edge.
Best for: everyone who’s going with more than two people
Boutique Inn — Southampton
The Capri Southampton
A redesigned mid-century motel that became one of the cooler Hamptons stays. Pool, great design, walking distance to Southampton village. For couples or solo travelers who want the boutique hotel experience without the corporate resort feel.
Best for: couples, design-focused travelers
Luxury Inn — Bridgehampton
Topping Rose House
A restored 1842 Greek Revival farmhouse with a Tom Colicchio restaurant on property, pool, spa, and the kind of service that makes you feel the price was worth it. The most elegant stay in the Hamptons that isn’t someone’s private house.
Best for: special occasions, anyone who wants the best
Waterfront Inn — Hampton Bays
Canoe Place Inn
A historic waterfront property on the Shinnecock Canal — full service spa, marina, restaurant, and waterfront access that puts you on the water in a different way than the ocean beach crowd. Worth knowing as an alternative to the main Hamptons scene.
Best for: boaters, water-lovers, off-peak visits
Hamptons rental reality in 2026
Peak summer weeks — July 4th, mid-July, and Labor Day — for desirable properties in Southampton and East Hampton book out 6 to 12 months in advance. Westhampton Beach has better availability and lower rates than the more famous towns while still offering the same Atlantic beach. September after Labor Day is the Hamptons at its most honest — same houses, same beaches, fraction of the crowd, significantly lower rates.
05 — Where to eat
It always has.
The Hamptons food scene has always punched above its weight — serious restaurants arrived here before they became a feature of every beach town, and the combination of wealthy clientele, fresh local seafood, and Long Island’s surprisingly productive farmland has sustained genuinely good cooking for decades. Here’s where to eat across the towns.
Westhampton Beach
flora
Currently the top-rated restaurant in Westhampton Beach — contemporary American with local ingredients, excellent service, the kind of cooking that earns its reputation quietly rather than loudly. The burrata is consistently praised. Make a reservation.
$$$
Ivy on Main
A Westhampton staple with an upscale American menu, professional service, and the kind of reliable excellence that brings people back year after year. The bar program is serious. Good for a long dinner on a summer evening.
$$$
Baby Moon
The beloved Italian institution — Sicilian recipes, enormous portions, dine-in or takeout, a Westhampton family staple for years. The kind of place where locals eat on a Tuesday and visitors discover on their third day. Not the trendiest spot in town. One of the most consistently good.
$$
Southampton & beyond
Sant Ambroeus Southampton
The Milanese café that became a Hamptons institution — espresso, pastries, beautiful pasta, the kind of Italian that doesn’t need to try hard because it’s the real thing. The summer lunch crowd is a scene. Worth joining once. The espresso is worth joining every morning.
$$$
Wolffer Estate Vineyard
In Bridgehampton — one of the most beautiful wineries on the East Coast. Rosé that’s become genuinely famous, estate wines that deserve more attention than the rosé gets, a tasting room and farm stand open daily. The sunset happy hour on the terrace is the Hamptons at its most effortless and most worth it.
$$
Nick & Toni’s
The East Hampton institution since 1988 — wood-fired Italian, locally sourced, the restaurant that celebrities and regulars have been filling for decades. The wood-roasted chicken is legendary. Reservations weeks in advance in July. Worth the effort.
$$$$
The Golden Pear
The Hamptons breakfast chain — multiple locations across the towns — that has been feeding summer people since 1988. Egg sandwiches, coffee, baked goods, the kind of no-nonsense morning fuel that gets you to the beach efficiently. Every Hamptons regular has a Golden Pear morning in them.
$
06 — Things to do
The beach, the wine,
and the things worth doing once.
Be on the beach — all day
The Hamptons beaches are the whole point. Wide, clean, Atlantic-facing, with consistent waves and the kind of ocean swimming that reminds you why people have been making this trip for a hundred years. We went boating and swimming as teenagers and came back as adults and swam again. The ocean doesn’t change. Cooper’s Beach in Southampton is consistently rated among the best in the country. Get there early for a spot.
Wine tasting at Wolffer Estate
The estate in Bridgehampton is genuinely beautiful — rows of vines, a handsome tasting room, a farm stand, and the most famous rosé on the East Coast. Even people who came for the beach end up here. The late afternoon light on the vineyard in summer is the Hamptons postcard that never gets old. Open daily; no reservation required for the tasting room.
Montauk Lighthouse
The eastern tip of Long Island, commissioned by George Washington in 1792, the fourth oldest working lighthouse in the United States. The drive out from the main Hamptons towns takes about an hour but the approach — past the Hither Hills dunes, through the Montauk moorland — is one of the better drives in the Northeast. The lighthouse sits on a bluff above the Atlantic and the view from the base is genuinely stirring.
Sag Harbor for an afternoon
The most livable and least performative of the Hamptons villages. The Whaling Museum tells the story of a town that was a major maritime center before the summer people arrived. The independent bookstore — Canio’s Books — has been a community anchor since 1980. The American Hotel bar is worth a drink regardless of what time it is. Walk the Main Street slowly and let Sag Harbor be what it is.
The Parrish Art Museum
In Water Mill, between Southampton and Bridgehampton — a serious museum in a spectacular building designed by Herzog & de Meuron. The permanent collection focuses on artists who lived and worked in eastern Long Island — Fairfield Porter, William Merritt Chase, Childe Hassam — and the building itself, a long low structure that echoes the barns of the Hamptons landscape, is worth the visit before you see a single painting.
Go in the off season
We enjoyed the Hamptons in the off season — the towns quiet, the beaches empty, the restaurants with actual tables available. October in Southampton is one of the genuinely underrated East Coast experiences. The light is different. The pace is different. The Hamptons reveals itself as a place rather than a production when the summer crowd goes home.
07 — Westhampton specifically
and the one we started with.
Westhampton Beach deserves its own section because it’s the Hamptons town most people overlook and the one that best represents what the Hamptons was before the money fully arrived. The westernmost of the Hampton towns, it’s 90 minutes from Manhattan by car when traffic cooperates, and direct LIRR service makes it the most accessible of the group.
The beach club culture in Westhampton — the clubs along Dune Road specifically — is old East Coast summer in the best way. Not flashy. Not performative. Just the Atlantic, a pool, a boat, people who have been coming back every summer for decades. We knew it in that era. It hasn’t fully left.
Dune Road
The barrier beach road running along the oceanfront — beach clubs, private homes, direct ocean access. The Hamptons beach experience at its most elemental. Cupsogue Beach County Park at the western end of Dune Road is public, beautiful, and significantly less crowded than the Southampton town beaches.
The village
Main Street Westhampton Beach has good independent restaurants, a cinema, galleries, and the kind of walkable village center that the more famous Hamptons towns have largely priced out of existence. Worth an evening browse.
Westhampton Beach Brewing Co.
The local craft brewery — a relaxed hangout with solid beer and the kind of unpretentious energy that Westhampton has always had more of than its famous neighbors. Good for an afternoon when the beach feels like enough for the day.
The LIRR option
Direct LIRR service to Westhampton from Penn Station — about 2 hours. The station is a short taxi or rideshare from Dune Road. This is the most accessible Hamptons town from the city without a car. The way we always went. Still works perfectly.
08 — Practical tips
this place actually teaches you.
Don’t drive on summer Fridays
The LIE on a summer Friday afternoon is 4.5 to 5 hours of your life you won’t get back. Take the Cannonball train or the Hampton Jitney. Leave very early or very late if you must drive. The traffic is not a myth.
Westhampton for first-timers
If you’ve never been to the Hamptons, start in Westhampton Beach. It’s the most accessible, the most down-to-earth, and the best introduction to what the Hamptons actually is underneath everything it performs.
September is the answer
The Hamptons in September — after Labor Day — is quieter, more honest, and significantly less expensive than July. The beaches are the same. The Atlantic is still warm. The restaurants have tables. Go in September once and you may not go back to July.
Book early for summer
Peak summer rentals and popular restaurants in East Hampton and Southampton book out months in advance. Westhampton has better availability. Wherever you’re staying, book accommodations before you book anything else.
Beach parking fills fast
Southampton and East Hampton town beaches require town parking permits for non-residents in summer. Either stay walking distance from the beach, rent a house with beach access, or use Westhampton’s more accessible public beach options.
The Hamptons is worth it
The production can be exhausting. The prices are real. The traffic is genuinely bad. And the beaches are still among the best on the East Coast. The Atlantic at Southampton on a clear July morning is the same Atlantic it’s always been. That part hasn’t changed. It won’t.
The beaches were always that good. They still are.
We went as teenagers — boating, swimming, eating well, relaxed in a way the Hamptons has largely forgotten how to be. We came back as adults from Manhattan and took the train and swam in the same ocean. We went in the off season and found the towns returning to themselves. The production changes. The Atlantic doesn’t.
The Hamptons is worth knowing despite what it became. Westhampton Beach for the most honest version. Southampton for the classic experience. Sag Harbor for an afternoon of actual town life. Montauk for the end of the road and the beginning of the open ocean. And September — always September — for the version that doesn’t need to perform.
The beaches were always the point. They remain the point.