Experience Long Island

Experience Long Island

A Week Long Adventure to Experience the Most While on Long Island, New York


Day 1. Old Westbury Gardens, Old Westbury, NY.

Step into the Gatsby-era in a stately furnished Charles II style mansion, home of the Phipps family. Tour the magnificent Old Westbury Gardens and explore the 160 acres of beautifully maintained gardens, sweeping lawns, fields, meadows and ponds. The children’s playhouse surrounded with flowers is one of my 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. Sagamore Hill National Historic Site, Oyster Bay, NY.

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. Long Island Museum of American History, Art, Carriages, Stony Brook, NY.

In Stony Brook, there are a handful of History & Heritage Museums. You’ll find the Long Island Museum of Art, History and Carriages, including 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.

Day 4/5. Wine Country, North Fork, NY.

Enjoy wine tasting at some of the best vineyards & wineries on the East Coast, in Long Island’s North Fork Wine Country. 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 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 beach front 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 Hamptons, NY.

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 or Fire Island Lighthouse.

Fire Island is a barrier beach comprised of many communities that are not accessible by car. Today you have a choice if you like to ferry over to Fire Island, Ocean Beach (via the Bay Shore Ferry). Or you can drive to Robert Moses State Park, Field 5, and walk the ½ 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.