Insider guide: How to holiday in the Hamptons

Follow our insider guide to this famous celebrity playground.

The Hamptons exist for most of us as a mirage of magnificent wealth hovering in the distance just out of reach. In reality, the term refers to a string of cedar-shingled historic villages on the East End of the South Fork of Long Island, about 175 kilometres from New York City. These villages are surrounded by mansions and endless white-sand beaches and, come summer, they are the epicentre of celebrity-studded parties, designer boutiques and see-and-be-seen restaurants.

Each of the Hamptons village enclaves has its own personality and style. Closest to Manhattan, Southampton with its soaring privet hedges oozes an Old Money ambiance. Heading east, you pass expansive mansions that have popped up in what once were potato and corn fields in Bridgehampton and Sagaponack, now some of the most expensive real estate in the United States. A little north on Long Island Sound, the former whaling town of Sag Harbor is a vibrant year-round community with some of the best restaurants on the East End. Next comes East Hampton, which was once more low key and arty than Southampton, but is now full of designer boutiques and Ferrari-driving bankers and entertainment industry types. Diminutive Amagansett is becoming increasingly hip with inns, bars and boutiques, while the tricked-up motels and seafood shacks in Montauk appeal to 20-something surfers and other hipsters.

In the past, it's been difficult for Aussies to join in the fun without renting a summer house for tens if not hundreds of thousands of dollars. Now, there are some chic tucked-away inns that give you access to the very best Hamptons style

Here's the insider lowdown to help you tack on a Hamptons getaway to your New York City sojourn.

The "summer season" goes from Memorial Day weekend (the last weekend in May) to Labor Day weekend (the first weekend in September) with the peak period being August, when the heat and humidity of the Big Apple become unbearable. Prices will be high whenever you come during this period, however if you stay midweek you're more likely to get better deals. The shoulder seasons of May and September are also excellent, with the weather reliably good and the prices much lower.

The Roundtree, Amagansett, has a sleek selection of shingled cottages, villas and studios which are dotted around expansive tree-shaded grassy grounds in the heart of Amagansett village. A delicious continental breakfast is served in rooms or on tables under the trees and every evening there's a s'mores happy hour around firepits where guests enjoy popcorn and toast marshmellows with complimentary champagne and other drinks. Other inns worth checking out include the Reform Club in Amagansett, the Maidstone in East Hampton and the Topping Rose House in Bridgehampton.

Avoid driving if you possibly can as the traffic is horrendous during summer. It's always wise to stay off Highway 27. Luckily, there are plenty of mansion-studded back roads which offer decidedly more atmospheric alternative routes. Take the Long Island Railroad from Penn Station, Grand Central or Jamaica, Queens; or the Hampton Jitney or Hampton Luxury Liner bus from several pick-up points in Manhattan. If you're staying in East Hampton, Amagansett, Bridgehampton or Sag Harbor you will easily be able to walk to restaurants, bars and shops from your accommodation. Most inns offer free bicycles which are the ideal mode of transport over the generally flat terrain.

You can also rent e-bikes or cars in Southampton, Bridgehampton and East Hampton, and don't forget the Turo car rental marketplace with super-convenient pick-up and drop-off arrangements. Whatever you decide to do, book early.

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All the Hamptons beaches require cars to have beach parking permits. On a bike you can access any beach including tucked-away gems such as Egypt and Wiborg ocean beaches, and Louse Point and Gerard bay beaches in East Hampton, Beach Lane in Wainscott, Gibson Beach in Sagaponack, Wyandanch and Gin beaches in Southampton, and Ocean Road and Mecox beaches in Bridgehampton.

Check out the live music line-up at the funky Stephen Talkhouse in Amagansett where famous (think Ed Sheeran) and not-yet-famous bands perform. Go to a performance or exhibition at East Hampton's Guild Hall, which has long been a bijou venue for world-renowned performing and visual artists who summer in the Hamptons.

Make an appointment to visit the Pollock-Krasner House in Springs. You'll see where the most valuable artwork in the Australian national collection, Jackson Pollock's Blue Poles, was painted.

Time your visit to coincide with some star-studded annual local events, which could range from the Hampton's Classic Horse Show, the Bridgehampton Polo Show and the Hamptons International Film Festival to the Artists and Writers Charity Softball Game, the Hamptons Beach Master Sand Sculpting Classic and, for something a little different, the Shinnecock Native American Powwow.

Standing the test of time, the American Hotel in Sag Harbor, with its flower-draped deck overlooking Main Street and its clubby interior, offers exceptional seafood, duck and steaks and the finest wine list in the Hamptons. Also in Sag Harbor is the superb Japanese restaurant Sen, the coastal chic locally inspired New American restaurant Page and Tutto il Giorno, a classy Southern Italian fine diner run by Gabby Karan (fashion designer Donna's daughter) and her Italian husband Gianpaolo de Felice. There's another outpost in Southampton.

In East Hampton, the place to be is the farm-to-table, Italian-leaning Nick & Toni's Tuscan-style farmhouse while Jean-Georges at The Topping Rose House in Bridgehampton sports an exceptional restaurant by acclaimed Michelin-star chef Jean-Georges Vongerichten.

Retro seafood shacks the Clam Bar and Lunch: Lobster Roll can be found on Highway 27 outside Amagansett on the way to Montauk.

The writer was a guest of the Roundtree Amagansett.

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