New York's Dutchess County Self-Drive

7 Nights

Dutchess County's Hudson Valley Self-Drive with NYC Stay

Dutchess County is in the heart of the Hudson Valley, which is famed for its magnificent scenery, historic mansions, cultural treasures and unique attractions - National Geographic Traveler named this region a Top 20 Best of the World Destinations!

June 2022


From great restaurants to glorious gardens and performing arts, creativity thrives amid inspiring landscapes. Celebrated chefs create farm-to-table cuisine at country inns and the world-famous Culinary Institute of America. With abundant farm markets, award-winning wineries, craft-breweries and food festivals, Hudson Valley dining is legendary.

Have the unique opportunity to enjoy a self-drive tour with your own hire car, to explore the amazing gems that this region has to offer. Based out of the amazing scenic city of Poughkeepsie, followed by a 3 night stay in iconic New York City to finish off an amazing week of adventure.

This offer includes:

  • 4 Nights at Poughkeepsie NY, Hyatt Place Poughkeepsie or Similar - B&B
  • 3 Nights at New York City, Westgate New York City Grand Central Grab’N’Go Breakfast
  • 4 Nights Car Hire Picking up from NYC Airport and dropping off at Poughkeepsie NY. Compact Car with Unlimited Mileage – Drop Fee Payable Locally at $68 per car
  • Ticket Entrance – The Edge, the highest outdoor sky deck in the Western Hemisphere.
  • Wine Tasting at Millbrook Vineyards, offering a guided 6 wine tasting.
  • Amtrak Ticket from Poughkeepsie, New York (POU) to NY Moynihan Train Hall at Penn Station, New York (NYP)
  • Return Shuttle Transfers from NYC Hotel to Airport
  • Direct flights to NYC from London Heathrow


Your day to day itinerary:

Day 1: Poughkeepsie

Arrive in vibrant New York, pick up your rental car and drive to Poughkeepsie where you’re going to stay the next 4 days. Once a bustling centre for industry along the Hudson River, the City of Poughkeepsie is going through a twenty-first century revival repurposing factory buildings as housing, eateries and art galleries. Poughkeepsie is home to Vassar College, where visitors can enjoy free admission to the small but significant collection at the Frances Lehman Loeb Art Museum and wander next door to view the stunning Louis Comfort Tiffany windows at The Chapel. Enjoy a vibrant dining scene with choices like Essie's Restaurant, Brasserie 292 and Mill House Brewing Company. For your first night in Poughkeepsie, we recommend a visit at the Shadows on the Hudson offering a breath-taking waterfront dining experience and mouth-watering cocktails.

Overnight: Hyatt Place Poughkeepsie - B&B

Day 2: Poughkeepsie- Rhinebeck – Staatsburg – Hyde Park

Today before you drive north to Rhinebeck, you must take a stroll along the Walkway over the Hudson, for some unmatched views of the Hudson River and beyond. Once a vital railway crossing, now the longest elevated pedestrian bridge in the world. Continue to Rhinebeck. It’s one of ‘Country Living Magazine’s’ Ten Most Charming Small Towns in America. For aviation fans, the Old Rhinebeck Aerodrome’s weekend air shows feature vintage aircraft, an extensive museum collection of planes dating back to 1903 and offer daily bi plane rides for the ultimate valley and mountains views. Enjoy lunch at "Tavern at the Beekman Arms", America’s oldest continuously operated inn, serving guests since 1766. After lunch drive South towards Staatsburg and Hyde Park. Visit Staatsburg State Historic Site a stunning estate that’s one of the last few surviving monuments to English country life. Down the road, experience the Home of Franklin D. Roosevelt National Historic Site, the FDR Presidential Library and Museum, and the Eleanor Roosevelt National Historic Site to get a glimpse into the life of America’s only 4-term President and his First Lady. Don’t miss a visit to The Culinary Institute of America – the world’s premier culinary college. Enjoy an interactive Philosophy of Taste tour. Make a reservation at any of the college’s three award-winning, student-run restaurants. Our favourite; the American Bounty Restaurant.

Overnight: Hyatt Place Poughkeepsie - B&B

Day 3: Poughkeepsie- Millbrook -Amenia

Today drive East towards Amenia. On the way, stop in Millbrook. This delightful village offers antique shopping and a popular literary festival each spring. Considered one of New York State’s top wineries, Millbrook Vineyards & Winery has been producing award-winning wines on its 130 acres for more than 30 years. After a guided tour, enjoy tastings of the current varietals: Chardonnay, Pinot Noir, Cabernet Franc, Tocai Friulano and Riesling (Wine Tasting included). Continue to Amenia. Derived from the Latin word “amoena,” meaning “pleasant to the eye”, Amenia boasts bucolic, scenic views, and access to the Harlem Valley Rail Trail. Visit the Wassaic Project, in the hamlet of Wassaic, which presents contemporary art inside the renovated, seven-story Maxon Mills grain elevator.

Overnight: Hyatt Place Poughkeepsie - B&B

Day 4: Poughkeepsie – Fishkill – Beacon

Today drive south to Fishkill and Beacon. Once host to Alexander Hamilton, the Town and Village of Fishkill are steeped in Revolutionary War history. The Van Wyck Homestead Museum offers local history exhibits and is the last surviving element of the 100-acre Revolutionary War Fishkill Supply Depot. Visit SplashDown Beach Water Park, a TripAdvisor Travelers' Choice U.S. Top 10 Waterpark, home to one of the biggest family raft rides in the Northeast and the state’s only zero-gravity water ride. Continue to Beacon. Voted the “#1 Coolest Small Town in America” by Budget Travel, the City of Beacon features a picturesque, walkable main street corridor with no shortage of delicious culinary options or immersive artistic experiences. Don’t miss Dia Beacon, a collection of large scale contemporary art housed in a former Nabisco box printing factory on the banks of the Hudson River and only a five-minute walk to Long Dock Park where you can rent a kayak, book a boat cruise to Bannerman Castle Island or just take in the expansive waterfront views. Enjoy the city’s growing craft beverage scene and sip local brews, spirits and more. Hike to the top of Mount Beacon for spectacular Hudson Valley views.

Overnight: Hyatt Place Poughkeepsie - B&B

Day 5: Poughkeepsie to New York

Today exchange your car hire for the Amtrak train which will whisk you from Poughkeepsie’s Station to New York’s Penn Station and the new Moynihan Train Hall. Once there, transfer to your hotel by Taxi. Filling the next 3 days with exciting things to do in New York City is ridiculously easy. Head to Broadway to take in a show; buy online well ahead of your trip, or try your luck with day-ofshow half-price tickets at the TKTS booth in Times Square. Stretch your mind at enriching museums both large, Metropolitan Museum of Art or Museum of Modern Art, and small, The Frick Collection or Morgan Library and Museum. Enjoy panoramic views of midtown Manhattan from the Empire State Building’s open-air observatory or from Top of the Rock at Rockefeller Centre. Alternatively for an unforgettable bird’s eye view, visit "The Edge", the highest outdoor sky deck in the Western Hemisphere, with a one-of-a-kind design. It’s suspended in mid-air, giving you the feeling of floating in the sky with 360-degree views you can’t get anywhere else. (Tickets Included).

Overnight: Westgate New York Grand Central Hotel - B&B

Day 6-8: New York

Get ready for an unforgettable day of sightseeing. New York City, deservingly called “the city that never sleeps”, offers something for everyone at all times of the day or night. Among the most visited attractions are Time Square, Central Park which houses the City Zoo, St. Patrick’s Cathedral, The Metropolitan Museum of Art, and the famous Brooklyn Bridge. After dark, the twin Gothic towers and strong steel cables make a striking silhouette against the night sky. Walking across the bridge is a huge thrill, particularly if you start from the Brooklyn side and view the Manhattan skyline as your stroll across. Of course, no tour of New York would be complete without a visit to America’s highest representation of freedom, the Statue of Liberty in New York Harbour, and the Empire State Building. For the artist at heart, the more established arts like dance, theatre, and music are superbly catered for. If shopping is what you fancy, you have come to the right place; the choice of shops is so extensive that it is almost numbingly exhaustive. In between sights, you can eat just about anything, at any time, cooked in any style.

Hotel: Westgate New York Grand Central Hotel - B&B


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