The Hamptons: Insiders Guide

If there’s one destination that guarantees a seductive mix of Hollywood glamour, society cool and beautiful white sand beaches it’s The Hamptons. Playground for the rich, very rich and very famous, The Hamptons is where New York society and half of Hollywood heads to for the summer – although which part of The Hamptons they head to depends on what they’re looking for. From Old Money mansions to Surfer Hangouts, there’s somewhere in The Hamptons for everyone.



Set on the Eastern End of Long Island, the Hamptons are made up of a string of villages and towns stretching along the coastline. Only a few hours drive from New York in the winter, it can take hours during the high season, meaning that the best way to get there is by train (or if you’re a celebrity by helicopter).



Southampton HouseKnown as a hub for Old Money families, Southampton is home to huge houses and serious wealth. This is where scions of banking dynasties, CEOs of banks and New York’s movers and shakers come to play.


East Hampton

East HamptonsCelebrity central, East Hampton is monied, but slightly glitzier, more Hollywood than Southampton with boutiques such as Tiffany’s and Elie Tahari on the Main Street.



Amagansett HamptonsMore low-key than East Hampton and Southampton, Amagansett has the feel of a sleepy village, albeit one with residents such as Gwyneth Paltrow and Sir Paul McCartney.



Montauk HamptonsIf you’re looking for a classic beach town vibe where shorts and flip flops, rather than designer dresses are de rigeur, then Montauk is where it’s at.


There’s so much to see and so much to do in the various parts of The Hamptons. Here are some of our favourite places…



Wölffer Kitchen, Amagansett

Wolffer Kitchen Hamptons

A relaxed restaurant with a rosé-inspired menu, what’s not to love? The restaurant is linked to the Wölffer Estate, which is a beautiful Long Island vineyard that makes a rosé that’s loved by many in The Hamptons. On Friday and Saturday afternoons in the summer (from 5pm) head to the Estate with a picnic blanket to drink wine and watch a jazz band play.


Bay Kitchen Bar, East Hampton

Bay Kitchen Bar

If you are looking to eat on the water, Bay Kitchen Bar in East Hampton is beautiful and the food is excellent. You can have a drink before dinner as you watch the sun set over the bay.


Inlet Seafood, Montauk

Inlet Seafood

Situated on an inlet close to Montauk, you can expect great seafood and sushi.


The Lobster Roll

The Lobster Roll

On the highway between Amagansett and Montauk, The Lobster Roll offers great seafood served in a basket. It was put on the map by its appearance in the TV show The Affair.  Also try Boswicks on the highway for seafood.



Because most people rent houses in The Hamptons, there aren’t a huge number of hotels. However, these recommendations are definitely worth visiting.


The Crow’s Nest, Montauk

Crows Nest Montauk

Near Montauk, the Crows Nest is a wonderful restaurant overlooking the bay. Rooms are small but cool with small cottages also available to rent.


The Surf Lodge, Montauk

The Surf Lodge

One of the hipper restaurant / hotels to stay and eat at is The Surf Lodge in Montauk. With queues of cars and people to get in in the summer, it’s also known for its concert series.


Sunset Beach, Shelter Island

Sunset Beach


Great food and a beautiful location, made all the more special by having to take a boat to get to Shelter Island. The twenty ocean-view rooms all have private decks.



Main Beach East Hampton

The beaches are pretty similar along the coast, so what you choose them on is vibe. Main Beach in East Hamptons (above image) has a friendly atmosphere and is a good choice for everyone. If you’re looking for a hipper feel then head to Gibson Beach in Sagaponack or Flying Point Beach in Water Mill. For surfing, Dutch Plains Beach in Montauk is a great spot (image below).

Ditch Plains Beach New York


Travel Contributor: Alex Gorton


Image credits: 1) 2) 3) 4) 5) 6) 7) 8) 9) 10) 11)