On The Road with the Roosevelts From Hyde Park to Oyster Bay

Packages Available: Spring, Summer and Fall
Tour Length: 4 Days/3 Nights

Welcome to the magical, gilded world of the Roosevelts. Upon arrival in Hyde Park, NY, you will be privileged to meet your historian and costumed guide, Franklin D. Roosevelt, who will escort you throughout your stay.
Franklin D. Roosevelt, 1912. REF# 47-96 4804(209) Franklin D. Roosevelt Library archivesTake a 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." Your guide, as FDR himself, will personally lead you through his Springwood estate and the first Presidential Library and Museum. Learn of the fascinating, historical happenings about the only President elected to four terms.

Be entertained with a day escorted by FDR’s fifth cousin, Teddy, as your guide transforms with mustache and pith helmet. Venture to Oyster Bay for a "bully" of an adventure. Visit Sagamore, the primary residence of Theodore and Edith Roosevelt from 1886. They lived there the rest of their lives.  This residence was also the "Summer White House" for seven summers.

Join in for a journey of dining and wining and rubbing elbows with the aristocrats, "On the Road with the Roosevelts."

Day One:

Arrive in Poughkeepsie, NY early afternoon, where you will be greeted by your costumed, full-time guide and historian, Franklin D. Roosevelt. Prepare yourself to be immersed into the gilded era and to discover the amazing lifestyle and historical impact of the Roosevelts.

Climb aboard for a 2-hour narrated cruise on the Hudson River. Experience the excitement of cruising under towering bridges, spanning the storied Hudson River. Glide past Gilded Age mansions and let your mind return to the romantic days, when steamships coursed the great Hudson bringing travelers to their "summer cottages."

After your cruise, arrive at your Poughkeepsie hotel. There will be time to relax and refresh before dinner.

Gather for an included dinner served at waterfront restaurant. Savor the flavors of spectacular Italian cuisine as you gaze out at the Hudson River.

Day Two:

After breakfast in the hotel, travel a short distance to Hyde Park where you will begin a day immersed in history.

Start with a guided tour of the home of 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. You will also visit the Presidential Library and Museum.

Eleanor Roosevelt, 1894. REF# 58-273 Franklin D. Roosevelt Library archivesYour next stop is at Val-Kill, the Eleanor Roosevelt National Historic Site. FDR encouraged Eleanor Roosevelt to develop this property as a place that 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.

Have lunch on your own at the on-site concession.

Your last stop in Hyde Park is at The Vanderbilt Mansion, one of America's premier examples of the country palaces built by wealthy industrialists. A superb example of its type, the mansion provides a glimpse of estate life, the social stratification of the period and the world of the American millionaire during the era historians refer to as the Gilded Age. Situated on the east bank of the Hudson River, the property includes pleasure grounds with views of the river and the distant Catskill Mountains. The property also has formal gardens, natural woodlands, and numerous auxiliary structures. The site’s main feature is a 54-room mansion designed and built between 1896 and 1899.

Due to its proximity to the Culinary Institute of America, fine dining abounds in this region. Dinner this evening offers not only exceptional cuisine, but also a museum experience as it is served in an historic canal house, built as a tavern in 1797. After dinner, there will be time to browse through the amazing antique displays and furnishings.

Day Three:

Teddy RooseveltAfter breakfast in the hotel, join your guide as he transforms into Teddy Roosevelt, and travel to Oyster Bay, NY. Along the way, your guide will entertain you as he shares fascinating tales of this American politician, author, naturalist, soldier, explorer and historian.

Your first stop, is at Sagamore Hill National Historic Site in Oyster Bay, NY. 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, visit the grounds, the home and The Roosevelt Museum.

Sagamore Hill is a rambling 23-room, Victorian structure of wood frame and brick. On the first floor is a large center hall, the library that served as Teddy’s private office, the dining room, kitchen and the drawing room that was Mrs. Roosevelt’s domain. Sagamore Hill was a working farm, where Teddy grew wheat, corn, hay, barley and rye and raised cattle and hogs. A three-acre garden provided vegetables and flowers.

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.

By this time you will be ready for lunch. Gather in an historic, old-English style pub and witness hundreds of photos that depict the turn of the century downtown Oyster Bay life, including oystering and seafood and Theodore Roosevelt himself.

After lunch, visit the Planting Fields Arboretum State Historic Park, Long Island’s premier public arboretum. This former Gold Coast estate is comprised of 409 acres of greenhouses, rolling lawns, formal gardens, woodland paths and outstanding plant collections. The original historic estate buildings remain, including the 65 room Tudor Revisal mansion, Coe Hall. Your visit includes a guided tour of the house and the gardens.

Late afternoon, board the coach and travel north along the Hudson River. Along the way, stop at the Historic Thayer Hotel at West Point. This property is a national treasure, visited by past US Presidents, world leaders and celebrities alike. Discover a captivating blend of over 200 years of military history combined with some of this finest food and service along the Hudson. This renowned restaurant sets the stage for a truly unique dining experience.

Return to your Poughkeepsie hotel.

Day Four:

After breakfast in the hotel, pack your bags and checkout. Before you depart for home, there is one more "must see" attraction. Visit the Walkway Over The Hudson, a linear walkway spanning the Hudson River. The "Walkway" is 212 feet tall and 1.28 miles long, making it the longest, elevated pedestrian bridge in the world. Walk across this majestically transformed railroad bridge and witness a 360-degree view of the Hudson Valley's breathtaking river and mountain views.


Packages Available: Spring, Summer and Fall
Tour Length: 4 Days/3 Nights

Your Package Includes:

  • 3 Nights accommodations
  • 3 Breakfasts
  • 1 Lunch
  • 3 Dinners
  • Narrated cruise on the Hudson River
  • Guided tour of the FDR Home
  • Visit to the FDR Presidential Library and Museum
  • Guided tour of Val-Kill Cottage
  • Guided tour of the Vanderbilt Mansion and Historical Site
  • Visit to Sagamore Hill
  • Tour Roosevelt Museum at Old Orchard
  • Guided tour of the home and gardens at Planting Fields Arboretum
  • Admission to the Walkway Over The Hudson
  • Baggage service for one piece of luggage per traveler
  • Travel with Franklin and Theodore, your costumed historian, guide
  • Accommodations for the coach driver
  • Taxes and gratuities

Pricing Information:

  • Call for custom pricing.