Mon, Oct 13: Depart Indianapolis for New York, New York. Upon arrival, travel north to Sleepy Hollow where you’ll explore Washington Irving’s Sunnyside, the romantic riverside cottage nestled along the banks of the Hudson River that has charmed visitors for generations. Hear about Washington Irving’s storied past and how he came to be America’s first internationally famous author. His characters, from the Headless Horseman to Rip Van Winkle, are global icons, and Irving’s legacy lives on at his whimsical estate. Stop in nearby Tarrytown for lunch on your own before a walking tour in Sleepy Hollow Cemetery where you’ll be enlightened on the significance of this famous cemetery. 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.  Head north along the river to The Thayer Hotel, located at the south entrance to the U.S. Military Academy at West Point, offering dramatic views of the Hudson River and the Hudson Highlands. Check in for a four-night stay and end the day’s journey with a Welcome Dinner. (Meal: Dinner)

Tue, Oct 14: Following breakfast in the hotel, depart for Hyde Park to tour a Gilded Age masterpiece—the Vanderbilt Mansion. The estate illustrates a way of life modeled on the English country house and is unusual today as so few examples have survived over the past century. Next, have lunch at the Franklin D. Roosevelt’s Presidential Library and Museum with 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 home, the place he retreated to in times of political crisis. 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)

Wed, Oct 15: This morning, tour the United States Military Academy at West Point with several stops including Battle Monument, Parade Field, and Trophy Point overlooking the Hudson River and the Plain. Spend some time exploring 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. Depart for Newburgh, where lunch is included at a local restaurant before boarding an afternoon cruise on the Hudson River. Cruise in comfort in the fully enclosed and climate-controlled riverboat or watch the passing scenery from its spacious upper deck. The two-hour cruise includes narration of historically significant sites. Following the cruise, cross the bridge into the emerging artist’s town of Beacon, boasting an abundance of Victorian architecture, collectible shops, art galleries, and a plethora of dining options to fill your leisure time this evening. (B,L)

Thu, Oct 16: Drive to Tarrytown for a tour of Kykuit, the John D. Rockefeller Estate. This hilltop paradise was home to four generations of Rockefellers, beginning with John D. Rockefeller, Sr., the founder of Standard Oil. Tour the expansive six-story house and the magnificent, terraced gardens. Have lunch on your own in Tarrytown before continuing to 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. Enjoy a special Farewell Dinner at Hudson House Restaurant, situated in the former village hall and jailhouse in the quaint village of Nyack. (B,D)

Fri, Oct 17: Check out of the hotel and depart for the historic Putnam County village of Cold Spring, long characterized by the row of antique shops along Main Street. Visit Boscobel for a guided tour of this early 19^th-century Georgian mansion and its gardens. Boscobel’s complex history represents several different periods and restoration philosophies. Built by British Loyalist States Morris Dyckman, the house has been restored to the Federal style of the late 18^th and early 19^th centuries and is highly regarded for its quality and authenticity. Many of its 1,000 period-era objects from Dyckman’s collection of English goods and Federal high-style furniture are on display. Spend some time in Cold Spring for lunch and last-minute souvenirs, then transfer to the airport for your flight home. (B)