5 things you must do on Long Island, New York's oceanfront playground

From the glassy waters of the north shore's natural harbours and bays to the crashing waves of the Hamptons and Fire Island on the south shore, you're spoiled for choice on Long Island. On the eastern tip of the south fork, the road dips and rises like a rollercoaster through sand dunes to Montauk, the mellow surfer's hangout that has become a hipster-chic destination. Well-heeled New Yorkers come to spend the weekend in classy resorts such as Gurney’s Montauk Resort & Seawater Spa with its luxurious oceanfront condos and restaurants of fine dining.  More affordable, Hither Hills State Park Campsite combines dune, beach and woodland walks of Russian olive, oak and pine. 

Choose top-rated Main and Coopers beaches for celebrity-watching in the Hamptons, Ditch Plains for its record-breaking waves, and for nature, Fire Island National Seashore with its 26 miles of federally preserved dunes, beaches and boardwalks on the 32-mile-long carless barrier island.

Long Island is fast gaining a reputation for producing world-class sparkling wines, summer-light rosés, fruity reds and crisp whites. Follow the wine trail to find out how Long Island's crafted wines are hand-picked, blended and fermented in the wineries 'where art and science meet', as one vineyard guide explains.

There are 60 wineries on the island. Highlights include Sparkling Pointe, providing tours through its vast silver vats to the Tasting House with its walls of dazzling Brazilian art, opulent chandeliers and high ceilings. Northeast of Sparkling Pointe, Kontokosta has a prime spot on the North Fork. The reconstructed barn, combining rustic beauty with contemporary minimalism, is strategically placed between vineyard and shore. The lawn, scattered with deckchairs and picnic benches (and occasional deer) slopes down to the sea where you can take your glass of wine and gaze out across the water to Connecticut. 

For seafood lovers, Long Island is a foodie paradise. Clams, shrimps, oysters, lobsters and crabs are harvested fresh from Long Island's waters. Tackle a hefty two-pound lobster, slip down a passion-inducing oyster, warm up on a steaming clam chowder or munch your way through a BLT (bacon, lettuce and tomato) crab sandwich - and taste the sea. 

Less than 30 miles from John F Kennedy Airport, Oheka Castle dominates the hill overlooking Cold Spring Harbor. Its creator, financier and philanthropist Otto Hermann Kahn, commissioned a grand summer residence to match the lavish parties he was planning. The result was a French-style chateau surrounded by parkland and formal gardens. Kahn went on to host some of New York's best-known movers and swingers including Charlie Chaplin, George Gershwin, Harpo Marx and Dorothy Parker.

While Oheka Castle brands itself as 'Europe in America', the hotel has a distinctly American feel to it. You can sense the ghosts of the roaring twenties, particularly in the Chaplin Room, the New York style bar, ballroom and wood-clad library. If you can't afford one of the luxurious hotel suites, book a tour or splash out on lunch in the restaurant overlooking the courtyard and gardens. For more turn-of-the-century glamour, visit Old Westbury Gardens and the Guggenheim Estate mansions. 

Yet further back in history, Long Island was a hotbed of resistance during the American Revolution. You can follow the Washington Spy Trail along Route 25A, where the George Washington Culper Spy Ring played a significant role in the revolution. Take a Tri-Spy tour (walking, biking and kayaking) and step back in time in the 1665 Brewster House – the revolution brought to life by actors. Here at the tavern, Joseph Brewster and his cousin (a Culper Spy Ring member) entertained the British troops while gathering information.

There are over 20 state parks and many more country parks, arboretums and preserves on Long Island – hard to imagine with New York and its suburbs spilling out across the island. Avalon Park and Preserve on the edge of Stony Brook offers a lake of snapping turtles, wildflower meadows and sculptures. 

On the North Fork, book yourself one of the ocean-chic Sound View condos raised on stilts over the private beach. Hire one of their bicycles and cycle to Greenport where you can take the ferry to sleepy Shelter Island. Shingle-clad houses with wraparound balconies and grandma rocking chairs dot the island's country roads before dropping to tiny harbours of bobbing boats. One third of the island is given over to Mashomack Preserve, a nature reserve of lakes, woods, wetlands, inlets and coves. It's a far cry from the bustling city. 

On the south shore, at Robert Moses State Park, amble along boardwalks through dunes and wetlands to Fire Island Lighthouse. From the top, take in the sweep of Jones Beach Island, Long Beach, and beyond the channels and bridges, the skyscrapers of Manhattan on clear days. 

Long Island has its fair share of picturesque settlements offering maritime museums, craft shops and trendy restaurants. From the southern tip of Shelter Island, another ferry crosses to the island of North Haven and from there a bridge leads to Sag Harbor on South Fork. This is a town of elegant white-painted clapboard mansions built for wealthy sea captains. One of them houses the Whaling Museum - the industry that brought the town prosperity. Page, on the handsome main street, possibly serves up some the best lobster sandwich on Long Island. 

Apart from Avalon Park and Preserve, Stony Brook offers quaint waterside shopping village with enough interest to fill a day. You can eat your way through the settlement – from chocolate at Chocolate Works to craft beer and cheese tasting at the superbly stocked Brew Cheese, and if still not full, check out Sweet Mama's diner for pure comfort food, cocktails and fluorescent-coloured ice-creams with names like Sponge Bob and Cookie Monster. Close by at Port Jefferson, the busy harbour runs ferries to and from Connecticut. Danford's on the waterfront makes a great base, but for the all-American breakfast experience head for Toast. 

For more information, check out www.discoverlongisland.com