Traveller's Guide: Long Island

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This sliver of New York State runs all the way from Brooklyn to Montauk, via retro amusements, pounding surf, vineyards and the Hamptons

The aptly named Long Island (it's the longest and largest in the contiguous United States) stretches east from New York City almost to the Connecticut/Rhode Island border, with Brooklyn at its western end and Montauk in the east. This sliver of land, 118 miles long and 23 miles wide, is part of New York State, bordered by the Atlantic Ocean to the south and Long Island Sound to the north. Among its dramatic dunes, long, sandy coastline, beach houses and boardwalks, you are sure to find your version of the seaside Americana fantasy.

First settled by native American tribes, it was later christened "Lange Eylandt" by the Dutch in the 17th century. In the 1640s eastern Long Island was settled by English Puritans, who later populated its western end. In 1776, it was the backdrop for the first major battle of the American Revolution as the Battle of Brooklyn, when George Washington-led American forces were forced to retreat back to Manhattan by the English under Generals William Howe and Charles Cornwallis.

In the 19th century, Long Island was still mainly rural, but advances in rail and road transportation meant that the eastern part of the island soon became suburbs of New York City – and a growing number of immigrant families moved in. Part of Long Island's North Shore also became a fashionable place for wealthy city-dwellers to build their weekend retreats. The iconic Brooklyn Bridge was built in 1883 – the first of the seven bridges that now connect Long Island with Manhattan.

Today, Long Island is still where millions of New Yorkers retreat to for the bracing Atlantic air, to hit the beaches, explore the unspoilt countryside and indulge in the retro amusements of Coney Island (www.coneyisland.com) and the vast expanse of Eisenhower Park (nassaucountyny.gov), which is larger than Central Park.

Heading further east, the day tripper's domains give way to more serene surroundings, not least the renowned holiday resort of the Hamptons. This string of quaint villages – Southampton, Bridgehampton, Sag Harbor, Sagaponack, East Hampton, Amagansett and Montauk – are some of America's quintessential beach destinations.

Nicknamed "the Hollywood of the East", these A-list enclaves dazzle with homes owned by Steven Spielberg, Martha Stewart, Calvin Klein, Ralph Lauren and Gwyneth Paltrow. Here, rappers rub shoulders with film stars, scions of Wall Street and the Old Money. You will find sophisticated boutiques and shops that wouldn't look out of place in Manhattan, restaurants and bars as well of plenty of broad, Atlantic-bashed beaches and open skies, which have inspired the work of artists such as Jackson Pollock. For the best people-watching, head to Gibson Beach in Sagaponack. A different picture altogether can be found in the farms and vineyards of the North and South Forks and picturesque Shelter Island, due east of the Hamptons.

Long Island is the prime arrival point for many British visitors to the US, in the shape of JFK airport – but not everyone realises that they have touched down there in their race to reach Manhattan. Before Idlewild (as JFK was originally known) was built, the island had also played an important role in aviation history. Charles Lindbergh set off on his historic flight to Paris from Long Island's Roosevelt Field in Garden City in 1927. Long Island was also home to New York City's first commercial airport, Floyd Bennett Field in Brooklyn, whose runway hosted historic flights by Amelia Earhart and Howard Hughes.

Several tour operators offer itineraries on Long Island, including Bon Voyage (0800 316 3012; bon-voyage.co.uk), Travelbag (0871 703 4698; travelbag.co.uk) and North America Travel Service (020-7499 7299; northamericatravelservice.co.uk). Five nights at the Village Latch Inn in Southampton costs from £1,049 per person including flights from Heathrow, car hire and room-only accommodation with America As You Like It (020-8742 8299; americaasyoulikeit.com). Alternatively, Virgin Holidays (0844 557 3865; virginholidays.com) offers one-week fly-drive holidays from around £958 per person including flights from Heathrow and a week's car rental from JFK.

For more details, contact New York State Tourism (020-7644 6115; nylovesu.co.uk) or see discoverlongisland.com.

All that glitters

Nothing sums up the 1920s extravagance of Long Island quite like F Scott Fitzgerald's novel The Great Gatsby (to feature this year as a Baz Luhrmann cinema remake). Fitzgerald's fictitious East Egg and West Egg were inspired by Cow Neck and Great Neck on the north of Long Island, an area known as the Gold Coast owing to the fabulous country mansions there. Several are open to the public, including Old Westbury Gardens, pictured (001 516 333 0048; oldwestbury gardens.org). Eagle's Nest, the Spanish Revival mansion once owned by William K Vanderbilt, now houses the Vanderbilt Museum (001 631 854 5579; vanderbiltmuseum.

Sands Point Preserve (001 516 571 7900; sandspoint preserve.org) is home to three mansions once owned by the Guggenheim dynasty. There are also trails that criss-cross forests, beaches and clifftops on the estate.

Surf's up

Montauk (onmontauk .com), also known as "The End", is one of the most laid-back towns on the island. This once-sleepy outpost has become the East Coast's coolest place to catch a wave. Its windswept, Ditch Plains beach, two miles from the village, attracts some of the world's best surf pros. Air & Speed Board Shop (001 631 668 0356; airand speedsurf.com) has daily board hire from $40 (£27).

The place to stay is Ruschmeyer's (001 631 668 2877; kingandgrove.com), which evokes the American summer camp of yesteryear in hipster style. Opened last summer, its 20 contemporary cabin-chic rooms start at $356 (£237), B&B.

Shore thing

Long Island has no shortage of beautiful beaches. Public beaches include Coney Island, Rockaway Beach and Brighton Beach, but others such as the six-mile-long beach at Jones Beach State Park (nyparks.com) charge an entrance or vehicle fee. For this you get rubbish-free surroundings and a good array of amenities. Long Beach (longbeachny.org) is one of Long Island's classic bay side beaches. Admission is $12 (£8) per day (9am-6pm), until September.

To get away from it all, take the ferry to car-free Fire Island National Seashore (nps.gov/fiis), a thin barrier island off the south shore with numerous beaches and trails to explore.

Grape escape

Tranquil North Fork (northfork.org) peninsula and its numerous vineyards is becoming the East Coast's answer to Napa Valley. Shinn Estate Vineyards (001 631 804 0367; shinnestate vineyards.com) in Mattituk has tours and rooms from $219 (£146), B&B.

Greenport is the place to dine out – try the Frisky Oyster (001 631 477 4265; the friskyoyster.com). North Fork Table and Inn (001 631 765 0177; north forktableandinn .com) in Southold is worth a detour.

Where to stay

Renting in the Hamptons can be eye-wateringly expensive in high season, with even the most modest cottage costing $5,000 (£3,300) a week. Hamptons Rentals (001 613 324 0009; hamptons rentals.com) has properties in all the villages. For camping with ocean views, Hither Hills State Park (nysparks.com) in Montauk has 168 pitches from $28 (£19) per night, although slots book up months in advance.

There's a current vogue for stylishly refurbished motels in the style of André Balazs's Sunset Beach (001 631 749 2001; sunsetbeachli. com) on Shelter Island (rooms from $345/£230). The place to be seen is The Capri (001 631 504 6575; capri southampton.com), which has a bathing club, poolside DJs and designer shops. Doubles start at $228 (£152). White Sands Resort Hotel, in Amagansett, (001 631 267 3350; white sandsresort.com) has double rooms and apartments with kitchens from $210, (£140) room only.

Getting there and getting around

Long Island has a year-round population, although further east, the holiday season runs from the end of May until early September. Combine a stay with a few days in New York. JFK Airport is served by British Airways (0844 493 0787; ba.com), Virgin Atlantic (0844 209 7310; virgin-atlantic.com) and Delta (0871 221 1222; delta.com) from Heathrow; American Airlines (0844 499 7300; aa.com) from Heathrow and Manchester.

The Long Island Railroad (001 212 878 7000; mta.info) departs from Penn Station and serves Manhattan, Brooklyn, Queens and Long Island from about $21 (£14) return. The Hampton Jitney (001 212 362 8400; hamptonjitney.com) is a coach serving Manhattan and JFK to both the North and South Forks of Long Island including the Hamptons and Greenport. Returns cost $49 (£33). The more luxurious Ambassador offers an express link from Manhattan to the Hamptons for $45 (£30) one way.

A car is ideal for exploring, although local permits are required to park at most beaches. In peak season, traffic jams are common and parking at beaches is tricky.

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