Luxury holidays in Long Island

East of the Big Apple, Long island is as diverse as they come with 125 miles of green farmland, vineyard-flanked villages and world-class beaches within its remit. The skinny isle is known best as a vacation playground for city-slickers, many of whom spend their summers in the high-society enclave of the Hamptons, on the island’s South Fork, where seaside charm is alive and well with old-school movie theatres, historic inns and roadside farmer’s stalls selling punnets of fruit and veg. But there’s more to this pretty peninsula than blue-blooded beach breaks and clapboard cottages. At its far end, in the likes of Shelter Island and Montauk, flashiness and fame is disguised by flip-flops and hoodies, while its lesser-travelled North Fork has been described by some as ‘the Brooklyn of Long Island’ thanks to its plentiful wineries and microbreweries and up-and-coming gastro scene.

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When to go

Summer sun will bring the crowds, but it also brings an exciting social calendar of street fairs, food festivals, pool parties, and carnivals. While autumn, is great for apple-picking on the North Fork. And, though winters this close to the Atlantic do get chilly, the peninsula boasts some of the best snow trails in the US.

Getting there

  • Planes

    JFK Airport, New York City’s main hub, is in easy proximity to the Long Island area, while New Jersey’s Newark airport takes just under an hour by car. If you’re travelling from within the States, you can land a little closer at Queen’s LaGuardia or Long Island’s MacArthur Airport in Ronkonkoma.
  • Automobiles

    The famed Long Island Railroad makes travelling around New York State fairly easy, but a car is essential if you’re looking to explore off the beaten tracks.