Pick up your hire car and drive to Long Island. Minutes from NYC and accessible via JFK, LGA and public rail, Long Island is home to the famed Hamptons, the 2025 Ryder Cup, LGBTQ+ haven Fire Island, Great Gatsby mansions and world-renowned Long Island Wine Country. Complement your NYC experience with pristine beaches, quaint villages, and revolutionary history. 

Make your first stop the Westbury estate which is a 23-room English manor house with traditional, formal gardens sprawling over 200 acres, it has been featured in over 25 movies and in dozens of television shows including The Gilded Age. Explore both Westbury House, with some of the most beautiful formal gardens in the world. Also visit the beautiful historic mansion, Oheka Castle, now a luxury hotel, located on the famed Gold Coast of Long Island. At Oheka Castle, you will discover a world of charming luxury and European ambience. Oheka is listed on the National Register of Historic Places. Enjoy a lunch here. 

Drive to Northport, approx. 20 miles and stay one night at North Port Village.

The Hudson River Museum offers engaging experiences for every age and interest with a growing collection of American art - exhibitions ranging from notable 19th-century paintings to contemporary art installations, a state-of-the-art planetarium, environmental teaching gallery and outdoor amphitheatre. Visit the Union Church with stained-glass windows by Marc Chagall, commissioned by the Rockefeller family. Henri Matisse's last work is here, too. 

Glenview, an 1877 house on the National Register of Historic Places, was designed by architect Charles W. Clinton and is in the grounds of the Hudson River Museum. The home was featured in Seasons 1 and 2 of HBO’s The Gilded Age, the popular Emmy Award-winning series from Julian Fellowes, creator of Downton Abbey.  

Stay two nights in Westchester. 

From Westchester drive to Nyack and visit the Edward Hopper House Museum & Study Centre. The House celebrates and advances the legacy of Edward Hopper through artifacts, programmes, and exhibitions inspired by the iconic painter. Tour the Roosevelt-Vanderbilt National Historic Sites of Hyde Park, Franklin D. Roosevelt Home on the Hudson is FDR's birthplace and final resting place offering guided tours, FDR Presidential Library & Museum is America's first presidential library and a state-of-the-art interactive exhibit about the Roosevelt era.

Visit the Culinary Institute of America in Hyde Park, the premier culinary school offers student-guided tours and dining at four award-winning restaurants. Cross the Walkway Over the Hudson, the bridge (circa 1888) is a NY State Historic Park; 64.6m above the Hudson and 2.06km across, making it the world's longest elevated pedestrian bridge. Enter at the east or west side of the river or ride the glass elevator for unbelievable views!

Dutchess County was established in 1683 as one of the original counties of New York. Nestled in the scenic Hudson River Valley, midway between New York City and the capital city of Albany. Dutchess County is 800 square miles of fascinating sites, lively events, and breathtaking vistas. 

Located just east of the Hudson River, with its majestic views of the Catskill Mountains, Rhinebeck is easily accessible to New York City, the Berkshires, Connecticut, and Upstate New York. Rhinebeck is a cultural mecca boasting galleries, museums, performing arts, independent film, and historic homes and architecture. Hiking and biking trails provide outdoor enthusiasts places to explore the natural beauty of the region. 

Stay two nights in Rhinebeck. 

Discover a fascinating mix of attractions and architectural styles, surrounded by tranquil farms, woodlands, and scenic lakes, including the 29-mile-long Great Sacandaga.

Saratoga Racecourse, America's oldest sporting venue is rated a World's Top 10 Sporting Venue by Sports Illustrated. Thoroughbred racing takes off in July and runs through Labor Day in early September. Saratoga Casino & Raceway presents thrilling harness racing, gaming, and top comedians, and musicians. For a unique experience, discover the beauty and excitement of world-class Saratoga Polo.

In Saratoga Spa State Park, Saratoga Performing Arts Centre presents the NYC Ballet, Philadelphia Orchestra, and rock and jazz concerts. Explore the National Museum of Racing's Hall of Fame and the park's mineral springs, and then relax in the Roosevelt Baths & Spa at the Gideon Putnam Resort. 

Stay 2 nights in Saratoga, possibly more if you visit in racing season.

Albany has a rich history dating back more than 400 years. When Henry Hudson arrived in 1609, the area was already home to the Haudenosaunee (Iroquois) and the Dutch had established a trading post. In 1797, Albany became the official capital of New York State. Since then, Albany has been a centre for banking, railroads, and international trade. Four New York state governors went on to become President of the United States. The telegraph, electric motor, and celluloid plastic were all pioneered here. Albany was also the point of origin for the first long distance airplane flight and the first passenger railroad. 

Stay one night in Albany. 

Drive via the very pretty city of Troy where all the horseshoes were made for the civil war. Also visit the Hart Cluett Museum featuring exhibits on one of Troy’s most historic figures, Samuel “Uncle Sam” Wilson, and tells the story of how Troy became “The Home of Uncle Sam” by an Act of Congress in 1961. It is worth being in Troy on a Saturday as it has a great market.  

Take an open-air ride on the Catskill Mountain Railroad or walk the Hudson River School Art Trail to see Thomas Cole's 19th-century paintings. Whether you bike along miles of mountain trails in the Catskill Preserve, swim in the sparkling lakes and hike to new heights on the mountain peaks, you're in for an outdoor adventure. Drive along the Upper Delaware Scenic Byway to dramatic vistas and quaint villages. Top stars perform all summer at Belleayre Mountain's Music Festival and the Bethel Woods Center for the Arts where a museum takes you back in time to the art and music of the 1960s. 

Stay one night in Catskills. 

Day 11 - Depart 

Drive back to New York City to fly home, approx. 150 miles to stay a few nights or to the airport for your flight home.