We used to take the Hampton Jitney out from the city — sometimes the train from Penn Station. The beaches were gorgeous. It was relaxed. That was before it became a production.
I first went to the Hamptons as a young teenager — my parents’ New York friends had a connection to Westhampton Beach, and for a few summers in the late 1970s and early 80s that’s where we ended up. The Hampton Jitney from the city, sometimes the train from Penn Station, and then the beach. Gorgeous sand, relaxed energy, boating on the bay, eating well. The Hamptons before anyone called it the Hamptons the way people call it that now. Then years later, a beach share house in Southampton — a completely different life, the same ocean. The Hamptons I know spans two eras and two versions of myself, and neither one looked like what you see in the magazines.
Which Hamptons Town Is Right for You?
Five distinct villages. Know which one you want before you book — they are not interchangeable.
Westhampton Beach
The western gateway to the Hamptons — less crowded than East Hampton or Southampton, more affordable, gorgeous beach, and the one that still feels most like what the Hamptons used to be. The Jitney stops here first.
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The oldest and most patrician of the Hamptons villages — historic estates, Main Street shops, Cooper’s Beach consistently rated one of the best in America. More understated than East Hampton.
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The luxury center — best restaurant concentration, most celebrated hotels, the social center of peak summer. Nick & Toni’s is here. More intense than Southampton. The celebrity version of the Hamptons.
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The tip of the island — lower prices, real surf, the lighthouse, Camp Hero. The anti-Hamptons Hamptons. For people who want the ocean more than the scene around it.
Search RentalsThe Hamptons I Remember
Westhampton Beach in the late 1970s and early 80s was a beautiful, relaxed place. The beach was pristine. People went boating. You ate well. Nobody was performing anything. It was just summer on Long Island’s South Fork.
My parents’ New York friends had a connection out there — the kind of access that came from knowing people, not from booking a hotel. We took the Hampton Jitney from the city, sometimes the train from Penn Station to Southampton and then a car the rest of the way. It was an easy trip from the city in those years, before the Friday traffic became its own weather system.
Westhampton was the first stop and in some ways the most genuine. Less famous than East Hampton or Southampton, which meant less production around it. The beach did exactly what the beach is supposed to do. The bay was right there for boating. The town was small and unpretentious. That version of the Hamptons — accessible, gorgeous, unhurried — is harder to find now but it hasn’t entirely disappeared.
Later, in the 1990s, a summer beach share in Southampton. A house full of people, the same ocean, completely different energy. Southampton has a formal quality that Westhampton doesn’t — the historic estates, the manicured hedges, the sense that this town has been doing exactly this for a very long time and intends to keep doing it. The beaches are extraordinary. Cooper’s Beach in Southampton is one of the finest stretches of sand on the East Coast.
Getting There
The Hampton Jitney and the Long Island Rail Road are still the right answer from the city. The car is still the wrong answer on a Friday afternoon in July.
Hampton Jitney
The iconic Hamptons bus service — departs from multiple Manhattan locations, stops through all the major villages, comfortable and reliable. Book in advance for summer weekends. The Jitney is not a concession to not having a car — it’s genuinely the better way to go. You arrive relaxed instead of arriving having survived the LIE on a Friday. hamptonjitney.com
Long Island Rail Road
Penn Station to Southampton, East Hampton, or Montauk. Roughly 2–2.5 hours depending on destination. The Cannonball — a direct express to the Hamptons — runs on summer Fridays and is exactly what it sounds like. No stops, no stalling, straight out to the South Fork.
By Car
About 2 hours from Manhattan in light traffic. Budget 4–5 hours on a summer Friday. Leave before noon or plan to leave after 7pm. The Southern State Parkway to Sunrise Highway is typically faster than the LIE. The Sunday return from Montauk on a peak summer weekend is its own experience — leave before noon or accept what happens.
The Jitney premium is worth it: You pay a bit more than the LIRR but the pickup locations are more convenient from Manhattan, the service runs frequently, and you don’t have to navigate a train connection. For most people making a Hamptons weekend, the Jitney is the move.
Westhampton Beach
The first Hamptons town on the South Fork and the one that still feels most like what the Hamptons used to be. Less famous, less expensive, less produced. The beach is as good as anything further east.
Westhampton Beach sits at the western end of the Hamptons corridor — the first village you reach coming from the city, and the one that gets the least attention in the magazine version of the Hamptons. That’s its advantage. The beach is gorgeous — wide, clean, the same Atlantic that Southampton and East Hampton are charging more to access. The town has real shops and restaurants without the East Hampton price premium. For the experience of the Hamptons without the performance of the Hamptons, Westhampton Beach is the answer.
Southampton
Southampton is the Hamptons at its most historically grounded — settled in 1640, one of the oldest English settlements in New York State. The Main Street has a quiet dignity that East Hampton’s doesn’t always maintain. The estates behind the hedgerows are the real thing, not new money trying to look old. Cooper’s Beach is consistently rated one of the best beaches in the United States — wide, pristine, well-maintained, with the full Atlantic doing what the Atlantic does.
East Hampton & Beyond
East Hampton
The social center of the peak-season Hamptons — the best restaurant concentration, the most celebrated hotels, the version of the Hamptons that ends up in the magazines. Nick & Toni’s has been the anchor dining destination for decades. Main Beach is extraordinary. The Maidstone hotel is the intimate luxury option. More intense than Southampton, more self-aware than Westhampton. Worth a visit, maybe less worth a week.
Sag Harbor
Former whaling port with genuine history, a working waterfront, an excellent independent bookshop, good restaurants, and significantly less pretension than the other villages. The Hamptons for people who find the Hamptons exhausting. An afternoon in Sag Harbor resets the scale of the whole trip.
Montauk
The tip of the island — the lighthouse built in 1796 at George Washington’s direction, Camp Hero State Park with its decommissioned radar towers, Ditch Plains Beach with its consistent surf. Lower prices than the villages. A genuinely casual vibe that the rest of the Hamptons can’t manufacture. Come here for the ocean, not the scene.
The Beaches
The beaches are what the Hamptons has always had and what no amount of development has diminished. Cooper’s Beach in Southampton. Main Beach in East Hampton. Coopers Neck, Mecox, Sagg Main. Wide, clean, fine white sand with the full Atlantic. These are genuinely excellent beaches — the best on the entire Long Island coastline — and they were excellent before anyone was famous for going to them.
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Book early for summer — July 4th and Labor Day weekend book out months ahead. September is the secret season: same beaches, half the people, lower rates.
What the Hamptons Is Now
The Hamptons of the magazines — the celebrity sightings, the hedge fund houses, the $45 lunches — is real. It’s also not the whole story. The beaches are unchanged. The ocean is unchanged. The bones of what made it worth going to in the first place are still there.
The production around it has grown significantly. The traffic on summer Fridays is genuinely one of the more unpleasant experiences available to humans in the Northeast. The prices at restaurants and hotels reflect decades of demand that shows no signs of softening. The celebrity-spotting economy has created a kind of Hamptons tourism that has nothing to do with the beach.
But Cooper’s Beach at 8am, before anyone is there, is still one of the best beaches on the East Coast. The Jitney still takes you there from the city in a few hours. Westhampton Beach is still the relaxed version. Sag Harbor still has the bookshop and the waterfront and the sense that not everything has been priced out of reason. The Hamptons is still worth going to — you just have to know which version you’re going for.
Quick Reference: The Hamptons
| Category | The Answer |
|---|---|
| Getting there from NYC | Hampton Jitney or LIRR from Penn Station — skip the car on Fridays |
| Best beach | Cooper’s Beach, Southampton — consistently rated one of the best in America |
| Most underrated town | Westhampton Beach — same ocean, less production, lower prices |
| Most charming | Sag Harbor — real history, working waterfront, less pretension |
| Best restaurants | East Hampton — Nick & Toni’s, book weeks ahead for summer |
| Skip the scene | Montauk — lower prices, real surf, the lighthouse |
| Secret season | September — same beaches, dramatically fewer people |
| Friday traffic | Leave NYC before noon or after 7pm — no exceptions |
| Best transport | Hampton Jitney — more convenient than LIRR for most visitors |
The Jitney still runs. The beach is still there. The water is still the same Atlantic. Some things about the Hamptons have stayed exactly as they were when I first took that bus out from the city as a teenager. Those are the things worth going for.