This Charlottesville & Albemarle County Itinerary at a Glance
Immerse yourself in the history of Charlottesville and Albemarle County, including homes of two former presidents, a Colonial-era tavern, a wide variety of culinary options, and world-class wineries. Add stops at amazing museums, cultural centers, and art exhibitions for a memorable visit.
Check out these great attractions and more:
- Michie Tavern
- University of Virginia
- Monticello Wine Trail
- Jefferson School African American Heritage Center
Looking for expert insights and fresh travel ideas? Download the latest issue of Leisure Group Travel for free and start planning your next unforgettable group adventure.
VA Day-to-Day Group Itinerary
Day 1 of Things To Do in Charlottesville & Albemarle County
Charlottesville and Albemarle County are home to world-renowned historic sites, including the homes of three of the country’s former presidents, making the area the perfect place to visit for the 250th anniversary of the nation in 2026. Visit Monticello, Thomas Jefferson’s home, and the University of Virginia, both of which are a single UNESCO World Heritage site. Jefferson was the third president of the United States, author of the Declaration of Independence, and the founder of the University of Virginia.
Michie Tavern is a great spot to enjoy lunch and a tour on your way to or from Thomas Jefferson’s Monticello. Located just half a mile from Monticello, this historic tavern dates to 1784, giving visitors a glimpse into the past and the chance to enjoy an 18th-century Southern dining experience.
Not far from Monticello and Michie Tavern is James Monroe’s Highland, the home of another U.S. President. Highland was purchased by Monroe in 1793 and was home to the Monroe family for nearly 25 years. This historical site was acquired by the College of William and Mary (Monroe’s alma mater) in 1974, and today, they host events, offer daily tours, and have a great museum shop.
Enjoy dinner at the Dairy Market, a new group food destination located in the historic Monticello Dairy Building. Located in Downtown Charlottesville, not far from the University of Virginia, the space is home to a dozen merchant stalls of varying cuisines, including a brewery, retail shops, and even a duckpin bowling alley.
Day 2 of Charlottesville & Albemarle County Attractions
Your group will start the day with a walking tour of the historic Grounds of the University of Virginia. See and learn more about the Lawn, the Rotunda, and UVA’s Memorial to Enslaved Laborers. This memorial honors the 4,000 to 5,000 enslaved people who lived and worked at UVA between 1817 and 1865.
Celebrating its 100th anniversary in 2026, the Jefferson School African American Heritage Center is an important place where your group can explore a permanent art exhibit, a rotating contemporary art gallery, and a robust calendar of events.
Day 3 of Charlottesville & Albemarle County Activities
Celebrating its 50th anniversary in 2026, the nearby Downtown Mall is a historic, pedestrian mall that is a great spot to enjoy a meal, shop, and stroll. Many restaurants offer outdoor dining, and groups will be able to choose from a variety of cuisines and price points. The Charlottesville area was recently named Wine Enthusiast’s Wine Region of the Year and features nearly 50 wineries on the Monticello Wine Trail. Experts at one of our regional wine tour companies will plan a customized route suited to your group’s interests.
Looking for expert insights and fresh travel ideas? Download the latest issue of Leisure Group Travel for free and start planning your next unforgettable group adventure.
Contact
- Anna Whitlow
- awhitlow@albemarle.org
