Virginia Itinerary: Presidential History in Charlottesville

History & Heritage, Virginia Group Tour Guide

The Itinerary at a Glance

Amid the beauty of the Charlottesville-Albemarle County countryside you’ll discover the world-renowned architectural masterpieces of our nation’s third President. Experience history, exceptional dining and a Virginia vineyard on this memorable tour.

5 Unique Experience on This Trip

  • University of Virginia Gardens and Rotunda
  • Monticello
  • Michie Tavern
  • James Monroe’s Highland
  • James Madison’s Montpelier

Duration: 3 Days

Available: Year-round

This Itinerary is Ideal For: Adults over 21

Itinerary Details

Day 1

Arrive mid-afternoon in Charlottesville at the University of Virginia. The architectural aptitude of Thomas Jefferson is on full display. Part of the original “Academical Village,” the Rotunda was patterned after the Roman Pantheon. The Rotunda is still the Grounds’ centerpiece and a great photo UVA Rotundaopportunity. Next, visit the six Gardens at the University of Virginia. The Pavilion Gardens are more formal, while the Hotel Gardens are more functional.

If time permits, continue with a driving tour of Historic Charlottesville before checking into one of the area’s group-friendly hotels.

Depart for dinner at one of Charlottesville’s outstanding restaurants. Many are chef-owned using fresh, local ingredients and located in buildings with a rich history.

Day 2

Enjoy breakfast at your hotel before departing.

Arrive at Monticello, where you’ll tour the David M. Rubenstein Visitor Center and Smith Education Center. You’ll see Thomas Jefferson’s World, a 14-minute introductory film. At the Robert H. and Clarice Smith Gallery you’ll view a series of innovative exhibitions of Jefferson’s influences and beliefs. Next jump on a shuttle to tour Monticello, his mountaintop home Michie Tavern Presidential history in Charlottesvilleand spectacular gardens.

Enjoy a late lunch at historic Michie Tavern. Costumed wait staff serve hearty fare in this 200-year-old converted log cabin. After lunch a tour gives groups a glimpse of the original inn and out buildings.

Arrive for a tour of Highland, the home of Jefferson’s close friend James Monroe, the fifth United States President. You’ll visit the early 19th century working plantation of a gentleman that held the most public offices of any President. Tour the newly renovated house and experience the life of a tireless public servant and his contributions.

Next, it’s off to Albemarle County for a tour and tasting at one of the award-winning wineries on the Monticello Wine Trail. The 30+ wineries are a tribute to Jefferson’s dream of Virginia being an ideal climate for grapes and winemaking.

Choose dinner tonight from an array of dazzling options. The Charlottesville dining scene competes with any major city. From European and Asian specialties to Southwestern and Southern favorites; formal or casual settings, all options are on the table.

This evening stroll Historic Main Street, the Downtown Pedestrian Mall – a European-style shopping plaza with more than 120 shops, restaurants, art galleries and more. Historic Court Square is where Jefferson, Monroe and Madison practiced law.

Day 3

Enjoy breakfast at your hotel before checking out.

Arrive at James Madison’s Montpelier and explore the home of the fourth President of the United States and architect of the Constitution, and his wife Dolley Madison. The Grills Gallery located inside the David M. Rubenstein Visitor Center exhibits permanent collections and rotating exhibits of the Madisons’ lives and the Gilmore Cabin, the first freeman’s site in the United States.

Lunch at the Exchange Café at Montpelier of made-to-order sandwiches and salads.

Depart for home with fond memories and appreciation for Thomas Jefferson and other Founding Fathers who built our nation.

To start planning your visit head to and for more Virginia group travel inspiration download a copy of the Virginia Group Tour Guide.


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