Luxury holidays in Montauk

Be honest: you’ve always wanted a legitimate reason to say ‘Meet me in Montauk.’ Located at the tip of Long Island’s South Fork peninsula, with the first lighthouse in New York state and six state parks, it’s famous for its fishing, which bodes well for holiday dining options. It’s also home to Ditch Plains Beach, arguably Long Island’s best surf spot; it gets busy on the weekends, but there’s no better place to rent a board and take on the waves.

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When to go

As standard with any vacational playground, summer sun will bring the crowds – on holiday weekends such as Memorial Day or 4 July you could spend more time stuck behind your wheel than on the beach. Your social calendar’s likely to have a bit more glitter during these months, though. The chilly Atlantic waters mean winters do get cold – but you’ll be bundled up by a wood-burning fireplace.

Getting there

  • Planes

    The nearest airport is Islip MacArthur (+1 631 467 3210;, 50 miles from East Hampton; JFK ( and LaGuardia are both around 80 miles away. If you’re feeling fancy, arrive at East Hampton Airport (+1 631 537 1130) by seaplane or helicopter delivering you from Wall Street and back with Sound Aircraft Services (+1 631 537 2202). Catch a flight from The Standard NY on their seaplane shuttle StndAIR with tickets starting at US$29 for off-peak trips(+1 855 786 3247).
  • Boats

    Shelter Island is linked to the South Fork by the South Ferry ( and Greenport by the North Ferry ( Boat-owning seafarers can take the Long Island Sound and moor up somewhere in Peconic Bay or Gardiners Bay, depending on which Hampton they are visiting.
  • Trains

    Long Island Rail Road’s Montauk line (+1 631 231 5477; is likely to get you there the quickest and cheapest – it makes five daily trips and takes two hours and 40 minutes to reach Southampton from New York City. It takes about three hours to reach Montauk, at the end of the line. The Cannonball Express, departing on Fridays from Penn Station in Manhattan, is even faster.
  • Automobiles

    You could try to persuade a cab driver to take you beyond the city limits but it’ll probably cost you over $350. Bus options along the Long Island Expressway include Hampton Luxury Liner ( and Hampton Jitney ( Taking your car or hiring one is a good idea – you’ll need it once you’re there as the towns are spread out.
  • Taxis

    The Hamptons is very spread-out so taxis are expensive. You’ll have to call in advance, but this can be a slow process. Book with East End Taxi (+1 631 324 0077), Sag Harbor Car Service (+1 631 537 7400) or Hampton Car Rentals New York (+1 631 329 1010).