Mon, Oct 12: Depart Indianapolis for New York, New York. Upon arrival, travel north along the scenic Hudson River to Tarrytown for lunch on your own before a walking tour in Sleepy Hollow Cemetery, which lent inspiration to the tale of Ichabod Crane. Admire the monuments, architecture, art and symbolism stopping at the final resting places of William Rockefeller, Andrew Carnegie, Washington Irving, and others along the way. Afterwards check in to your local hotel and conclude the day with a welcome dinner shared with fellow travelers! (Meal: Dinner)

Tue, Oct 13: Following breakfast at the hotel, check out and depart for a tour of Lyndhurst Mansion, a Greek Revival fortress of massive proportions originally built in 1838 for the mayor of New York City. Subsequent owners added changes to the house and grounds. Now part of the National Trust for Historical Preservation, Lyndhurst is surrounded by classic estate landscaping, which includes an aviary and a magnificent greenhouse. Continue to the historic Putnam County village of Cold Spring, long characterized by the row of antique shops along their quaint Main Street. Have time for lunch and souvenir shopping before continuing to the town Hyde Park. Check into the Inn at Bellefield for the next three nights and enjoy dinner at a favorite local restaurant. (B,D)

Wed, Oct 14: Enjoy a leisurely morning at the hotel before transferring a short distance to Kingston. In 1777 Kingston was designated as the first capital of the state of New York, today it is a small but vibrant city where you will board a narrated sightseeing cruise on the Rip Van Winkle II. Cruise comfortably in the fully enclosed and climate-controlled lower deck or watch the passing scenery from the spacious, shaded upper deck. Take in beautiful views of the Hudson River as you sail by many sites of historical interest found along the waterfront. Grab a bite to eat on your own before departing for a spectacular estate you may have spotted from the water—Wilderstein Historic Site. The Queen Ann-style mansion is set on 40 beautiful acres and is Hudson Valley’s most important example of Victorian architecture. Dive into the history and significance of this historic home on a guided tour before transferring to the charming village of Rhinebeck. Enjoy an evening of free time for shopping and dinner on your own before returning to the hotel. (B)

Thu, Oct 15: Spend today in historic Hyde Park! Begin with a visit to Franklin D. Roosevelt’s Presidential Library and Museum, which set a precedent as the very first presidential library, and have free time to explore rarely seen artifacts that convey the dramatic story of the Roosevelt era. The saga continues with a guided tour of Roosevelt’s Springwood, the family estate he retreated to in times of political crisis. Then stop at the Eleanor Roosevelt National Historical Site, known as Val-Kill Cottage, and get a peek into Mrs. Roosevelt’s life, her time as first lady and her work with human rights. Later this afternoon, explore the world’s premier culinary college, the Culinary Institute of America, on a student-lead campus tour, followed by dinner at one of their student-staffed restaurants. (B,L,D) 

Fri, Oct 16: Check out of the hotel and depart for the United States Military Academy at West Point. Take a guided campus tour with several stops including Battle Monument, Parade Field, and Trophy Point overlooking the Hudson River and the Plain. Then have time to explore the West Point Museum, whose holdings span the history of the United States Military Academy at West Point, the military history of the United States Army, the history of warfare, and the profession of arms. The West Point Visitors Center houses a full-scale cadet barracks room, a cadet uniform, and videos on cadet life. Following an included lunch, transfer to the airport for your return flight home. (B,L)