“Charlottesville, where the beauty is as deep as the history”

HISTORIC Tours

We offer three amazing tours that highlight the lives and contributions of three of America’s founding fathers, as well as the enduring legacies they left behind for all of us to explore and appreciate.

Allow yourself to travel back in time as you discover the fascinating historical wonders found throughout our area. Each and every one of our carefully guided tours includes a convenient stop where you can enjoy food and beverages, ensuring a comfortable and enjoyable experience.

OUR TOURS INCLUDE THE FOLLOWING:

  • Safe, courteous and knowledgeable driver

  • Clean and comfortable vehicle

  • Bottles of water

  • Tour tickets

  • One wine flight (4-6 wines)

Charlottesville Area Historic Tours

  • James Monroe's AshLawn Highland

    Founding Father's 2 day tour

    Our immersive two-day Founding Father's Tour beautifully highlights the rich wine heritage and captivating history that make Charlottesville an exceptional destination. We begin with a comprehensive guided tour of Monticello, immersing guests in the legacy of Thomas Jefferson, and conclude the day with a relaxing glass of wine at Jefferson Vineyards, allowing time to unwind and appreciate the surroundings. On the second day, we start with an insightful visit to the Ashlawn Highland estate of James Monroe, followed by a memorable lunch paired with exquisite wine tastings at the stunning Barboursville Vineyard and Ruins. To complete the experience, we enjoy a detailed guided tour of James Madison's Montpelier, providing a perfect ending to a day rich in history and flavor.

    Jefferson’s Monticello

    Monroe’s Ashlawn Highland

    Jefferson Vineyard

    Barboursville Vineyard and Ruins

    Madison’s Montpelier

  • James Madison's Montpelier

    Founding Father's day tour

    There are several fascinating historic properties and delicious wines to enjoy on this wonderfully busy and enriching day. We first travel to scenic Orange County, located just north of Charlottesville, where you will take an insightful guided tour of James Madison's Montpelier estate. Afterward, we continue with a visit to the beautiful Barboursville Vineyards and Ruins, where you can enjoy a delightful lunch paired with a glass of their excellent wine. Our final stop will be a guided tour of Monticello, the iconic home of Thomas Jefferson, offering a captivating glimpse into American history.

    Madison’s Montpelier

    Barboursville Vineyard and Ruins

    Jefferson’s Monticello

  • Thomas Jefferson's Monticello

    UNESCO world heritage tour

    This exceptional tour takes us to two of Thomas Jefferson's most iconic masterpieces, the University of Virginia and Monticello, both honored as UNESCO World Heritage sites in 1987 for their outstanding cultural significance. Our journey begins with a detailed guided tour of the picturesque University Lawn and the distinguished Rotunda at the University of Virginia, where history and architecture blend beautifully. Next, we head to Monticello's David M. Rubenstein Visitor Center, a thoughtfully designed space featuring an excellent gift shop and numerous engaging exhibitions dedicated to Thomas Jefferson and the rich history of Monticello. For a convenient and pleasant break, you can enjoy a quick bite and refreshing drink at the Monticello Farm Table Cafe before proceeding to your in-depth guided tour of the historic estate.

    The Rotunda and Academic Village at UVA

    Michie Tavern

    Jefferson’s Monticello

    Jefferson Vineyards