5-day trip to Poughkeepsie, New York Itinerary

Start your day with a hearty breakfast at Mill House Brewing Company. Afterward, visit the Vanderbilt Mansion National Historic Site to explore the grand estate and its beautiful gardens.

For lunch, head to Amici's Restaurant and savor their delicious Italian dishes. Afterward, take a scenic drive to Beacon, a nearby city, and visit the Dia:Beacon art museum to admire contemporary art.

Enjoy a relaxing dinner at Crew Restaurant & Bar and indulge in their flavorful dishes. Afterward, explore the charming town of Rhinebeck, another nearby city, and visit the Olde Rhinebeck Aerodrome for a unique vintage aviation experience.

Start your day with a delicious breakfast at Essie's Restaurant. Afterward, visit the Vassar College campus and explore its beautiful architecture and gardens.

For lunch, head to Schatzi's Pub and Bier Garden and enjoy their selection of craft beers and German-inspired dishes. Afterward, take a scenic drive along the Hudson River and visit the Olana State Historic Site for breathtaking views and art.

Enjoy a memorable dinner at Crave Restaurant & Lounge, known for its diverse menu and elegant ambiance. Afterward, relax and unwind at Millbrook Vineyards & Winery and indulge in a wine tasting experience.

Start your day with a delicious breakfast at Twisted Soul Food Concepts. Afterward, visit the Dutchess County Fairgrounds and explore the local agricultural heritage and enjoy various events and exhibits.

For lunch, head to Bonefish Grill and savor their fresh seafood dishes. Afterward, take a scenic drive to the charming village of Rhinebeck and explore its boutiques, art galleries, and historic sites.

Enjoy a delightful dinner at Red Robin Gourmet Burgers and Brews and indulge in their mouthwatering burgers. Afterward, visit the Bardavon 1869 Opera House for a live performance or concert.

Start your day with a delicious breakfast at Poughkeepsie Ice House on the Hudson. Afterward, visit the Franklin D. Roosevelt Home National Historic Site to explore the former residence of President Roosevelt and learn about his life.

For lunch, head to Mahoney's Irish Pub & Steakhouse and enjoy their Irish-inspired dishes. Afterward, take a scenic drive along the Hudson River Valley Wine Trail and visit Nic L Inn Wine Cellar on the Hudson River Valley Wine Trail for a wine tasting experience.

End your trip with a delightful dinner at Caffe Aurora Poughkeepsie, known for its Italian cuisine. Afterward, take a leisurely walk along the waterfront at Waryas Park and enjoy the beautiful sunset over the Hudson River.