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Are the Hamptons Overrated? The ‘Good Guys’ Weigh In

July 26, 2025

The Hamptons loom large in every New Yorker’s summer moonage daydream, but the shine fades fast when you factor in $42 lobster rolls, four-hour bar lines, and a $100 Uber to Montauk.

On Good Guys, hosts Josh Peck and Ben Soffer peel back the hydrangea curtain and talk money, miles, and the madness of “the happening spot.” Their assessment reflects a growing sentiment among younger travelers. Simply put: The Hamptons have become a pricey headache, and the vibe is slipping.

Fortunately, the East End of Long Island is not just billionaires with beachfront mansions. But it’s also not exactly the scrappy dive-bar crowd either, and it’s increasingly difficult for most visitors to access the authentic community that exists beyond the velvet ropes and Instagram hotspots.

Are the Hamptons overrated?

For the uninitiated, “The Hamptons” is a catch-all phrase that refers to two townships on the East End of Long Island: Southampton and East Hampton. There are also several small towns within those townships, including Sag Harbor, Water Mill (where many celebrities reside and which is often associated with “The Hamptons” in popular perception), Sagaponack, and Montauk.

Hierarchy matters out east, and Soffer lays it bare: “If you’re on the beach, Josh, it’s a trillion dollars. It doesn’t matter what Hampton you’re in. If you are beachfront and have a house on the beach, you’re going to spend at least $15,000,000 for a shack. It doesn’t matter where you are.”

When even the comedians are citing eight-figure shacks, young professionals eyeing a beach weekend are increasingly calling the Hamptons overrated—and they’re starting to look elsewhere.

The price tag isn’t cute

Soffer follows with, “And I would say that there are very, very few people, if any, that would rent a house on the water in the Hamptons. It just doesn’t make sense. Because if you’re gonna spend $500,000 a month to be on the water, you might as well just put a down payment on a house. Like, it’s such a ludicrous amount of money.”

So, unless you’re casually choosing between a down payment and a July rental, you’re better off elsewhere—like the happening, hip, nowhere-near-as-pretentious Fire Island.

Surf Lodge, $50 guac, and the scene fatigue

Peck asks the question everyone outside the velvet rope wonders: “Are you doing any of, like, the Hampton-y things? Like, what is it? The Surf Lodge? And why is that place a thing? That’s, like, the real happening spot. Right?”

Soffer confirms the myth and the markup: “Surf Lodge is just great music, great food. They’ll bring you a lobster roll to the table. Okay? And is it like I’ve heard, it’s around $50 for guac and chips? It’s expensive for sure.” (Although the Surf Lodge’s menu pricing is far from cheap, $50 for chips and guacamole is a bit of an exaggeration.)

Even if you snag a table, Soffer reminds you how they work it: “You have a table minimum, and you can use it towards food. So even if the guac is $50, you don’t care.”

Except that plenty of younger millennials and Gen Zers do care because they’re not blowing their rent money on dipping chips in this economy.

Traffic, distance, and two-hour treks

Beyond cost, logistics are a beast. Soffer notes, “You’re driving so far. For instance, if the house were in Montauk and I lived there, and it was just down the road, no problem. Right? But I’m, like, a solid hour from it. The Hamptons stretch from west to Montauk. It could take you two hours just to get from one part of the Hamptons to the other.”

This is to say nothing of limited public beaches, packed parking lots, and overpriced rides. It’s clear why so many 20-somethings are pivoting to places that don’t require a second mortgage or an air traffic controller to plan a night out.

Montauk “used to be” chill—now “it’s ruined”

Nostalgia creeps in when Soffer says, “Montauk used to be the beach town. It used to not be built up. There was no Surf Lodge. I would go out there with my parents. We’d stay at a bed and breakfast. It was really like a hotel. It was more rustic. It was still beautiful water, and now it’s basically ruined.”

“Everyone you hate in the city wearing shorts”…but regular folks exist

Peck drops Jon Stewart’s classic burn: “The problem with the Hamptons and why the Jersey Shore is superior is that the Hamptons is everyone you hate in the city wearing shorts in the woods.” Soffer pushes back—sort of. “If you wanna find those people, you can find them,” he says. “But if you wanna find regular folk, I’d say that 90 percent of the Hamptons are people that live here full time.”

Yes, full-timers exist, but tourists aren’t exactly accessing that community. They’re stuck in four-hour lines outside Stephen Talkhouse, fighting for resident-only beach access, and getting hedges instead of house-peeping.

So… should you still go?

If you crave authenticity, there are better bets. The hosts gush over the Jersey Shore dive-bar energy, and other locals have high praise for Fire Island, Long Beach, and Atlantic Beach. Today, the Hamptons rarely give gritty, communal fun. They give curated, expensive “lore.” The Hamptons are gorgeous, but for most budgets and patience levels, they’re overrated.