Charlottesville, Virginia: Historic Estates & Presidential Legacies

Charlottesville, Virginia: Historic Estates & Presidential Legacies



In the scenic Virginia Piedmont, the world of Thomas Jefferson and his contemporaries comes to life. Spend a week retracing the steps of our nation’s founders from our “home base” in charming Charlottesville, Virginia. Delight in visits to Jefferson’s iconic Monticello and Poplar Forest estates, a morning spent strolling the grounds of James Madison’s Montpelier, and tours of wineries and private properties in Albemarle County. Experience Charlottesville’s nationally recognized restaurant scene, from fine dining along the Downtown Mall to rustic Southern fare at a 19th-century tavern. Between the bustle of the University of Virginia grounds and rolling hills of the Virginia countryside, a week spent in Charlottesville will be an unforgettable retreat.

Pricing from
Trip Type
Closer to Home, Group Travel Tour
Departure Dates
Nov 6, 2022 - Nov 10, 2022


Boar’s Head Resort
Relax at the Boar’s Head Resort, the only AAA Four Diamond resort in Charlottesville. With a warm and intimate ambiance and exceptional southern hospitality, this award-winning hotel offers elegant rooms and suites, excellent dining, a vast array of recreational activities, and a luxury spa. Situated on a 600-acre property in the foothills of the Blue Ridge Mountains, the Boar’s Head boasts an array of plant and wildlife viewing opportunities. Guests and locals are invited to explore the trail system that meanders deep into the woods directly in stride with the resort’s Audubon-certified golf course. A stroll on the resort’s pathways will take guests past lakes and ponds, some low-lying wetlands, and even a historic cemetery.


  • Craig A. Reynolds, PhD

    Craig A. Reynolds, PhD

    Craig A. Reynolds is an art historian specializing in the Enlightenment and Early American Republic (1700 - 1850), more specifically the design and architectural work of Thomas Jefferson and his followers. Craig is presently Curator of the Virginia State Capitol, first designed by Jefferson in 1785, as well as Curator of Capitol Square, a historically significant landscape and outdoor public sculpture garden.


CANCELLATIONS & REFUNDS: Cancellation by participant must be made in writing to ISDI and is effective only upon acknowledged receipt by ISDI. There is a non-refundable registration and planning fee of $500 per person regardless of cancellation date. Written cancellation received by ISDI on or before July 8, 2022: full refund minus $500 per person registration and planning fee. Written cancellation received by ISDI between July 9 and September 22, 2022: full refund minus $1,700 per person cancellation fee (includes registration and planning fee). Written cancellation received by ISDI on or after September 23, 2022: no refund. Tour registration is non-transferable. In the case of cancellation, substitutions are not allowed. After the tour has commenced, no refunds will be issued for any reason including, but not limited to, unused portions of tour. If the tour is cancelled by ISDI or National Trust Tours due to low enrollment, active registrants will receive a full refund of all tour payments.


  • day 1

    SUNDAY, NOVEMBER 6 Arrivals in Charlottesville

    Upon arrival in Charlottesville, Virginia, transfer independently to the luxurious Boar’s Head Resort, situated on a 600-acre property in the foothills of the Blue Ridge Mountains,
    yet close to Charlottesville’s historic center. Gather in the late afternoon for a stroll on the resort grounds before enjoying a welcome dinner with fellow travelers. (D)

  • day 2

    MONDAY, NOVEMBER 7 Montpelier & Barboursville

    This morning, visit the home of U.S. president and Founding Father, James Madison. The historic home, grounds, gardens, and outbuildings at Montpelier are beautifully preserved and maintained today by the National Trust for Historic Preservation. The construction of Montpelier began around 1764 and, upon completion at the end of the 18th century, the plantation home stood as one of the largest brick dwellings in Orange County, Virginia. Back along the outskirts of Charlottesville lies the Barboursville Ruins, the preserved remains of a brick mansion designed by Jefferson. The mansion was constructed by Jefferson’s workmen for his close friend and political ally, James Barbour, former governor of Virginia, U.S. senator, and secretary of war. Although a Christmas Day fire destroyed everything but the brick walls, the ruins are a magnificent memory of an era lost in the mists of time. Following lunch, be treated to a wine tasting at Barboursville Vineyards. Then visit a privately-owned plantation house outside Charlottesville. Return to the hotel for an evening at leisure.

  • day 3

    TUESDAY, NOVEMBER 8 Poplar Forest & Lynchburg

    Depart for Jefferson’s Poplar Forest, the plantation house that served as a summer retreat for the president. Recently, the structure has been restored using only tools, materials, and techniques that were available during the 19th century. Jefferson was still president and residing in Washington, DC when construction began in 1806, which greatly influenced his decision to build Poplar Forest at a great distance from his public life. Pause for lunch at a charming riverfront restaurant in downtown Lynchburg. On the way back to Charlottesville, visit a private 19th-century estate steeped in Virginia history. The remainder of the afternoon and dinner are at leisure.

  • day 4

    WEDNESDAY, NOVEMBER 9 Mr. Jefferson’s Charlottesville

    The morning begins with a lecture by Study Leader Dr. Craig Reynolds. As today is dedicated to Thomas Jefferson’s legacy in and around Charlottesville, the day’s touring starts at the illustrious Monticello, America’s most prominent Palladian estate. Gain exclusive access to the second and third floors, including the iconic Dome Room, where an on-site historian will discuss architectural features and the complexities of family life at Monticello. Enjoy lunch at Michie Tavern, opened in 1784 and still serving traditional Southern fare to this day. Return to Charlottesville to explore the University of Virginia campus—fondly referred to by students and residents as “Grounds.” Experience Mr. Jefferson’s university, from the iconic Rotunda to the Lawn and visionary Academical Village. At the Albert and Shirley Small Special Collections Library, view original university documents detailing the activities of students, faculty, and administrators dating back to the 19th century. In the evening, gather for a farewell dinner celebrating the end of an enriching exploration of Charlottesville and rural Virginia.

  • day 5

    THURSDAY, NOVEMBER 10 Departure

    Following breakfast, depart at your leisure.

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