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Travel to the Hudson Valley region and immerse yourself in history, scenic beauty and culture. National Geographic Traveler named the Hudson Valley one of the top 20 must-see destinations in the world! Step back in time and discover why Franklin D. Roosevelt stated, “All that is within me cries out to go back to my home on the Hudson River.” 


Venture to Oyster Bay for a “bully” of an adventure. Visit the grounds of Sagamore, the primary residence of Theodore and Edith Roosevelt (from 1886), also known as the Summer White House. 


Join in for an outing filled with dining, wining and rubbing elbows with the aristocrats, “On the Road with the Roosevelt’s.”


Spring, Summer and Fall
4 Days / 3 Nights



Begin your “On the Road with the Roosevelt’s” adventure with an early morning departure.


Upon arrival, climb aboard for a 2-hour narrative tour along the historic shoreline of the Hudson River. You will witness sites such as: West Point, the United States Military Academy, World’s End, the deepest point of the Hudson River, the Saugerties 


Light House and Bannerman Island, an historic island known for its warehouse built to resemble a Scottish castle!


After your cruise, board the coach and travel north to Poughkeepsie, your overnight destination. Along the way, stop at the Benmarl Winery where you will partake in a tour and a taste. Situated on 37 acres overlooking the Hudson River Valley, this winery is the oldest vineyard in North America. Your visit includes a guided tour of the vineyard, a tasting of six wines, a souvenir glass and a bottle of one of their award-winning wines to enjoy along your trip.


Late afternoon, check into your full-service Poughkeepsie hotel. The stylish waterfall and custom hand-blown Chihuly glass lighting fixtures welcome you into a warm and relaxing atmosphere. There will be time to relax and refresh before dinner.  After a busy day steeped in history, you will be ready sit back, relax and quench your thirst. No taste-test needed at this stop---you’ll know right away that you are drinking beer!  A stop at the Mill House Brewing Company is the ideal solution. This brewing company has become a major player in the explosive craft beer 


scene coming out of the Hudson Valley.  Learn the fascinating story behind the owners and enjoy samples of their incredible brews. 



Start your day with a hearty breakfast buffet at the hotel. Then board the coach and travel a short distance to Hyde Park where you will begin a day immersed in history.

Your visit starts at Val-Kill, the Eleanor Roosevelt National Historic Site. FDR encouraged Eleanor Roosevelt to develop this property as a place where she could develop some of her ideas for work with winter jobs for rural workers and women. She named the spot Val-Kill, loosely translated as waterfall-stream from the Dutch language common to the original settlers of the area. Val-Kill was the only place Eleanor Roosevelt called home. It was here that she pursued her political and social interests, wrote her “My Day” column and worked on the Universal Declaration of Human Rights.


Next, visit the National Historic Site of the home, museum and library of President Franklin D. Roosevelt. This National Historic Site preserves the Springwood Estate, the birthplace, lifelong home and burial place of the 32nd President of the United States. Learn the story of the Roosevelt presidency beginning in the depths of the Great Depression and continuing through the New Deal and World War II. Your visit includes a self-guided tour of the Presidential Library grounds, Museum and Springwood.


Following your tour, have lunch on your own at Hyde Park Brewery or the Ever-Ready Dinner. 


Depart Hyde Park early afternoon and travel a short distance to Staatsburgh State Historic Site is the elegant country home of Ogden Mills and his wife 


Ruth Livingston Mills. Overlooking the Hudson River and the Catskill Mountains, Staatsburgh is a fine example of a great estate built by America's financial and industrial leaders during the Gilded Age (1876 - 1917). Also known as the American Renaissance, this period in American history was marked by America's rapid economic growth and emergence as a world power. Darius Ogden Mills, father of Ogden Mills, established the family fortune by investing in banks, railroads and mines. Ogden Mills, like his father, was a noted financier and philanthropist. In 1882 he married Ruth Livingston, whose family had been prominent landowners in the Hudson Valley since the 17th century. In 1890, Ruth Livingston Mills inherited her childhood home and property which had once belonged to her great-grandfather, Morgan Lewis, the third governor of New York State. 



Return to the hotel for time to relax and refresh. Then, board the coach and travel just down the street to your dinner destination Mahoney’s, that was once the Vassar Brewery. Matthew Vassar, founder of Vassar College, started the brewery in the 1800’s. The brewery moved roughly sixty thousand barrels of beer annually. Still visible on the restaurant floor is a section of the brewery’s grain auger! Dine on New American fare served in a relaxed and historic setting. Owner, Pat will provide a more in dept history of the building and then treat you to a mixology lesson. You will learn how to create the famous, “The Roosevelt” cocktail and bring home a souvenir.


DAY 3 

After breakfast in the hotel, board the coach and travel to the Sagamore Hill National Historic Site in Oyster Bay. Sagamore Hill was the home of Theodore Roosevelt, 26th President of the United States, from 1885 until his death in 1919. Roosevelt named his home Sagamore, the Algonquin word for chieftain, the head of the tribe. During Roosevelt’s time in office, his “Summer White 

House” was the focus of international attention.  During your stop, explore the natural surroundings and historic grounds, the Visitor Center, Bookstore and witness exhibits and videos at The Roosevelt Museum. (Note: Tours of any indoor structures will depend on current park restrictions) A self-guided cell phone, audio tour is provided.

The museum was built in 1937 for General Theodore Roosevelt, Jr. and was his family home until 1960.  The exhibits and films portray Theodore’s political career, family life at Sagamore Hill and his children’s lives.


Depart Sagamore Hill and travel a short distance to Huntington Village. This quaint town has an array of restaurants where you may scatter to have lunch on your own. There will also be time to visit the charming shops and witness the local architecture. Described as a “Charles Dickens storybook downtown,” Huntington Village is as popular with the locals as it is with the tourists.


Early afternoon, board the coach and travel north along the Hudson River to the historic Thayer Hotel at West Point. This property is a national treasure visited by past US Presidents, world leaders and celebrities alike. Gather in an elegant private room with floor to ceiling windows offering magnificent views of the Hudson River. An afternoon High Tea featuring a selection of freshly prepared finger sandwiches, warm scones and a variety of pastries will be one of the most memorable moments of your trip.


Depart The Thayer and travel back to your hotel for time to refresh. Your Farewell Dinner, is served at Poughkeepsie’s award-winning waterfront 


restaurant, Shadows on the Hudson. Perched on a cliff 40 feet above the Hudson River and 50 feet from its eastern bank, this prime location gives you one-of-a-kind, truly grand views of the Mid-Hudson Bridge to the north and miles of open-river to the south. 

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DAY 4 

After breakfast in the hotel, pack your bags and bid farewell to the historic Hudson Valley. However, before you depart, there is one more “must see” attraction. The Walkway Over the Hudson is a linear walkway that spans the Hudson River. It is 212 feet tall, 1.28 miles long and it is the longest, elevated pedestrian bridge in the world.

Upon arrival, meet your docent and begin your walk on the bridge. The docent will explain the history of the bridge and its as you walk along the majestically transformed railroad bridge for a 360-degree view of the Hudson Valley’s breathtaking views. You will walk partway over the bridge and then return to the parking lot. After your time on the bridge, receive your “souvenir merit badge for walking.”


With a lunch stop on your own along the way, you’ll arrive back home.


We look forward to helping you book your next adventure! 


Your package includes:

  • 3 Nights accommodations

  • 3 Breakfasts

  • 3 Dinners

  • Hudson River Cruise

  • Tour, taste and a bottle of wine at the BenMarl Winery

  • Guided tour of the Vanderbilt Mansion

  • Guided tour of the FDR Home

  • Free time to explore the FDR Library and Museum

  • Guided tour of Val-Kill

  • Tour and Taste at the Mill River Brewery

  • Tour of the grounds at the Sagamore Hill National Historic Site 

  • Time to explore Huntington Village on Long Island

  • High Tea at the historic Thayer Hotel

  • Docent lead walk on the Walkway Over the Hudson

  • Souvenir Gift

  • Baggage service for one piece of luggage per traveler

  • Accommodations, baggage, breakfasts and dinners for the coach driver

  • Taxes and gratuities (NOTE: Gratuities for the coach driver and local guides are not included and are at your discretion based on service.)

24/7 Personalized Service

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