Charlottesville Tours & Activities 2025

Charlottesville , Virginia

From $ 95.00

A very comfortable and stylistic a tour and tasting some of Virginia’s finest vineyards and wines. It’s very private and enjoyable for couple looking for an intimate getaway, a small group celebrating a special occasion, a bridal party, or a business team looking for a change of scene. You are making the right choice to experience the natural beauty of Mountains while driving to one of the best winery in historic Charlottesville. It is an exciting time of touring and wine tasting. Your vehicle type will depend on your group size.

Charlottesville , Virginia

From $ 235.00

Ole Crow Tours warmly invites you to explore the very best that Virginia’s renowned wine region has to offer in comfort and style. Simply sit back, relax, and let us handle all the details, carefully ensuring a seamless and unforgettable experience for you and your guests to truly savor every moment. On this thoughtfully curated tour, you’ll be enjoying visits to 3 carefully selected wineries located on the scenic eastside of Charlottesville. This journey will take us through the charming Keswick area, once home to Thomas Jefferson’s old stomping grounds, a region rich with history, natural beauty, and timeless elegance.

Charlottesville , Virginia

From $ 168.00

Discover the legacy of Thomas Jefferson on this full-day guided tour to Monticello, his historic estate perched atop a scenic mountaintop in Charlottesville, Virginia. Explore the architecturally stunning home where Jefferson shaped the ideals that defined a nation, filled with personal artifacts, inventions, and writings. Stroll through his lush gardens, a blend of natural beauty and botanical experimentation. Gain insight into plantation life and learn the stories of the enslaved individuals who lived and worked at Monticello, offering a deeper understanding of America’s past. Admission includes entry to museum, exhibits, and historic grounds for a well-rounded experience. With expert guidance and comfortable transportation, this tour is perfect for history lovers and cultural explorers. Enjoy a smooth, hassle-free journey with air-conditioned transport and convenient pickups from Washington, D.C., Rockville, MD, or Falls Church, VA—making it easy to step into history for the day.

Charlottesville , Virginia

From $ 394.00

Please join our knowledgeable, entertaining guides in an unparalleled tour of the best of food and culture on the world-famous UVA Corner.

Charlottesville , Virginia

From $ 235.00

If you want to overload your senses, this could be the one. This tour combines two of the area's top vineyards, which not only produce wonderful wine but also provide an unforgettable culinary experience. One of the stops is also recognized for its architectural design, while the other for its architectural ruins.

Charlottesville , Virginia

From $ 419.00

The Downtown Mall Food Tour is a unique and memorable way to visit one of America's top college towns.

Charlottesville , Virginia

From $ 235.00

We would like to personally invite you to join us on an unforgettable journey through the beautiful countryside of Charlottesville and the surrounding area. As you enjoy tastings of some of Virginia's finest and most celebrated wines, you will be completely immersed in the rich history shaped by Thomas Jefferson’s lasting influence on the region. This experience promises to be both relaxing and enlightening, blending the natural beauty, exquisite flavors, and historical depth unique to this area.

Charlottesville , Virginia

From $ 49.60

Skip the stress and confusion of finding a taxi upon arrival at the Charlottesville International Airport. Instead, book this private airport transfer service and enjoy convenient, reliable, comfortable private transportation from the airport to your destination.Just relax and leave the driving to us. Transfer services are available 24 hours a day, seven days a week. Choose from a Luxury Sedan transfer for 3 passengers or a 6 passenger SUV.

Charlottesville , Virginia

From $ 305.00

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.