Long Island Vacation Travel Guide | Expedia

Long Island stretches eastward for 115 miles, from the New York boroughs of Brooklyn and Queens to the windswept bluffs and rollers of Montauk Point. In many ways Long Island is the story of America. It's a story of Native Americans, some of whom welcomed European settlers ashore in 1637, and of those who resisted. It's a story of pirate treasure and hardy whalers, of revolutionary war and the beginnings of a nation. It's a story of some of the world's greatest industrialists, artists and adventurers. And binding these epic stories together is mile upon mile of some of the nation's best beaches and the warm summer rays of sunshine. Take the short train ride from Manhattan, take off your shoes and step onto the sands of Long Beach. For many, Long Beach's iconic two-mile boardwalk and endless rows of volleyball nets is where Long Island all begins. From here, Long Island's protective barrier islands continue in an almost unbroken chain all the way to West Hampton Island. Halfway along the chain, experience the wild, windswept beauty of Fire Island National Seashore. Take the short hike from Robert Moses State Park to the Fire Island Lighthouse, which for generations of immigrants sailing to New York was their very first glimpse of America. Many of those immigrants and their descendants went on to create industrial and financial empires like the world had never seen. And it was on the island's northern shores where they poured their vast fortunes into mansions and summer retreats that rivaled the great estates of Europe. In 1902, financier Howard Gould built a medieval castle at Sands Point to impress his wife. She wasn't, so a more intimate Tudor-style mansion was quickly built. Unfortunately, that didn't do the trick either, and the couple soon parted ways. Not to be outdone, in 1921, the insurance magnate William Robertson Coe built his own Tudor-style manor at Planting Fields in nearby Oyster Bay. Coe spared no expense on the 65-room manor, even importing the windows from the ancestral home of Anne Boleyn. During the Prohibition era, Coe stocked his basement with almost half a million dollars' worth of liquor, ensuring the good times would never end. It was homes and lifestyles like these that inspired the settings and characters for F. Scott Fitzgerald's classic, The Great Gatsby. While some of these great mansions have been preserved as snapshots from a gilded age, others have been repurposed. The Vanderbilt Museum and Planetarium is centered around the family's stunning Spanish Revival mansion, while the Nassau County Museum of Art has taken up residence in the Georgian mansion that was once home to members of the Frick dynasty. But it wasn't just tycoons who were drawn to Long Island's Gold Coast. Sagamore Hill was the much-loved home of one of America's most popular presidents. Theodore Roosevelt lived here from 1885 until his death in 1919, filling his home with trophies from his expeditions to Africa and South America. The house today is much as it was during Roosevelt's lifetime, right down to his famous Rough Riders hat, which hangs from an elk antler as if it was tossed there only yesterday. The Cradle of Aviation Museum and nearby Hempstead discover how Long Island launched generations of aviators into the wild blue yonder and the stars. From the first barnstormers to the record-breaking flights of Charles Lindbergh, from the aerial dogfights of World War II to those first steps upon the moon. For over a century, Long Island was at the center of America's aviation and space adventures. Nearby, continue your flight into aviation's past at the historic hangars of the former Republic Aviation Company. Here at the American Air Power Museum, warbirds from the island's golden years of aviation are lovingly preserved by many of Republic's former staff. Once you've explored the treasures of Long Island's Gold Coast, head further west to discover the riches of Suffolk County. In the mid-1800s, well-to-do New Yorkers were drawn to the natural beauty, unspoiled beaches, and restorative air of Long Island's East End. The pioneer settlement of Southampton Village soon became a summer retreat. Today, it's a place where history and affluence have blended as smoothly as the spirits in a Long Island iced tea. Give your credit card a workout in the exclusive boutiques, galleries, and restaurants of Main Street and Jobs Lane. And if shopping's not your thing, you'll find plenty of history to keep you occupied here, too. Take a walk through Southampton's early times at the Historical Museum, whose centerpiece is the home of a 19th century whaling captain and his family. All around the home are smaller structures which give a window into Long Island life long before the paparazzi came to town. Today, Southampton Village is the heart of the Hamptons, the home of some of the USA's most expensive real estate. It's a place where today's movers and shakers come to escape behind the 20-foot-high hedgerows of their summer homes. The real estate here might be out of reach for most folks, but thankfully, the sun and sand of Cooper Beach is free for all to enjoy. It's not just vacationers who adore the mild maritime climate of Suffolk County. The grapes like it here, too. Over the last 50 years, the potato fields of old have been replaced by vineyards. One of the largest is the Wolfer Estate, a little slice of Tuscany where 50 acres of vines thrive in the South Fork Loam. Just up the road at the Channing Daughters Estate, the grapes are still picked by hand and crushed by foot. Here, creativity is expressed not just in the daring varietals and blends, but also in the many sculptures which dot the estate. Artists, visionaries, and dreamers have long been inspired by the Hampton light. Spend an inspirational hour or two at the Parrish Art Museum, which celebrates artists who lived and worked in the East End, such as Andy Warhol, Ray Lichtenstein, and Chuck Close. Just a short drive away at the Longhouse Reserve, the sculptural works of Buckminster Fuller, Yoko Ono, and William de Kooning sit in perfect harmony with nature. But for modern art lovers, there is no more hallowed a destination than the former home of Jackson Pollock and Lee Krasner. It was here, on the outskirts of East Hampton, where one of the 20th century's most important artistic couples lived and painted. Step into the barn and walk upon the paint-splattered floor where Pollock threw himself body and soul into his visionary masterpieces, which shook the art world forever. Another East Hampton house worth visiting is the Home Sweet Home Museum, where the simple pleasures and practicalities of English settlers in the 1700s come vividly back to life. Past has also been beautifully preserved in the nearby town of Sag Harbor, an historic whaling port immortalized in Moby Dick. Behind the old whaler's church, pay your respects at the old burying grounds, where American raiders defeated the English Redcoats in the Battle of Sag Harbor in 1777. Just a 30-minute drive east from Sag Harbor is Montauk, a place that the laid-back locals refer to as The End. Once the stomping ground of pirate Captain Kidd, today it's the perfect place to catch a wave or fish or to hike the coastal trails of Shadmore State Park. Fifteen years after the Battle of Sag Harbor, America's first president, George Washington, commissioned Montauk Lighthouse on Long Island's easternmost point, climbed the iron steps to the top to take in the views. But before you descend, close your eyes for a few moments and feel the wind turn the pages of this incredible island, a place that has played center stage in some of America's greatest stories, a place that continues to attract dreamers, visionaries, and those who appreciate the finer things in life, a place that continues to send its inspirational and reassuring light out into the world.