Long Island Classic Touring

Gatsby-era history, wine country and famous beaches

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Widely known for the rich and famous who regularly visit the quaint villages and sparkling beaches of its Hamptons region, Long Island has always drawn famous characters to its shores. Teddy Roosevelt, Charles Lindbergh, Walt Whitman, just to name a few, are immortalized here. And other famous people from New York began migrating to Long Island’s Gold Coast decades ago. But it’s not just the actors, politicians, artists and adventurers who make up the most famous components of Long Island’s culture. Visit Long Island and explore some of our famous film sites, our famous lighthouses or famous beaches.

Day 1 touring Long Island

At the Old Westbury Gardens in Old Westbury, step into the Gatsby era in a stately furnished Charles II style mansion, home of the Phipps family. Tour the magnificent home and explore the 160 acres of beautifully maintained gardens, sweeping lawns, fields, meadows and ponds. The children’s playhouse surrounded with flowers is a favorite. Stay and lunch at the outdoor Café in the Woods. Overnight on the South Shore, where you can take an evening walk and play some games on the famous Jones Beach Boardwalk.

Day 2

At Sagamore Hill National Historic Site, take a guided tour of President Theodore Roosevelt’s home, a rambling 23-room Victorian structure of wood frame and brick. Throughout the house you will see and feel Mr. Roosevelt’s personality and achievements. Walk the trails and visit the Orchard Museum filled with memorabilia and historic documents. Then continue on Rte. 25A onto Cold Spring Harbor or Huntington for lunch.

Are you up for more one more historic home? The Vanderbilt Mansion and Planetarium is located in Centerport off 25A. The 24-room Spanish-Revival Mansion will take you back to the celebrated Gold Coast era. Tour the home, stroll the gardens and tour the Hall of Fishes Marine Museum on the property; the evening planetarium shows are great. Overnight on the North Shore.

Day 3

At the Long Island Museum of American Art, History and Carriages, you’ll find one of the largest collections of horse-drawn carriages in the country. Drive into the historic village of Stony Brook and look up at the eagle on the post office as it flaps its wings on the hour. Back on Rte. 25A continue to Port Jefferson for lunch and a walk around town. Head east, overnight in Riverhead and spend a little time shopping at the Tanger Outlets.

Days 4 and 5

In the Wine Country around North Fork, enjoy wine tasting at some of the many vineyards. Continue east to Greenport, a charming fishing village where you will find a great selection of restaurants for lunch. Take the North Ferry over to Shelter Island, drive Rte. 114 and take the South Ferry to Sag Harbor. Now you are in the Hamptons, and when you continue on route 27 will end up at Montauk Point. Stay overnight at a beachfront property near town. It’s time to relax, enjoy the surf, water sports, fish, visit the Montauk Lighthouse, hike the trails or go horseback riding on the beach.

Day 6

The world-famous Hamptons, known as being the home of many of NY’s rich and famous celebrities, consist of many towns all with a little different flavor. Walk the towns, drive the small, winding roads near the beaches to get a glimpse of the fantastic homes, and stop in at famous Main Beach in East Hampton, voted one of the top beaches in the country. If you’re interested in art, stop at the Pollack Krasner House in Southampton or the Parrish Art Museum in Bridgehampton or one of the many galleries you’ll see along the way. Continue west on Rte. 27 and overnight on the South Shore.

Day 7

Fire Island is a barrier beach comprised of many communities that are not accessible by car. Today you have a choice if you would like to ferry over to Fire Island or Ocean Beach (via the Bay Shore Ferry). Or you can drive to Robert Moses State Park, Field 5, and walk the half-mile dune walk to tour Fire Island Lighthouse. When you’re done, you can walk the beach into the town of Kismet on Fire Island. Overnight on the South Shore.

This itinerary is compliments of the Long Island Convention & Visitors Bureau and Sports Commission.

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