Top Charlottesville Private Sightseeing Tours

Discover the beauty of Skyline Drive, a stunning 100-mile stretch through Shenandoah National Park. This self-guided audio experience transforms your drive into an engaging journey, revealing the rich history and natural wonders of the Blue Ridge Mountains. Encounter sweeping overlooks, hidden waterfalls, and captivating tales of the land's past as you cruise along. Perfect for both newcomers and seasoned travelers, this tour lets you explore at your own pace—just drive, look, and listen to the stories unfold along the way. — Self-guided audio experience through Shenandoah National Park — Explore over 100 miles of scenic mountain roads at your own pace — Learn about the geology, history, and local lore of the Blue Ridge — Ideal for first-time visitors and seasoned explorers alike

Enjoy a private, chauffeured wine or beer tour through the Charlottesville wine region with Golden Limousine LLC. Our professional chauffeurs provide door-to-door service in luxury vehicles, allowing you to relax and enjoy Virginia wineries or breweries without the stress of driving. Tours are customized to your preferences and ideal for couples, groups, celebrations, and special occasions. Highlights: -Private, non-shared experience -Professional chauffeur -Flexible itinerary -Luxury SUV transportation -Local Charlottesville wine expertise

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.

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.

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.

With the beauty of the Blue Ridge Mountains surrounding the quaint vineyards of Virginia, this private wine excursion delivers a peaceful and harmonious experience in the great outdoors. A private chauffeur will cruise you and your guests from historic Charlottesville to the countryside. Spend the day touring the area and sampling wines from multiple wineries. On the Wine Trail, you’ll have your choice of which tasting rooms to visit and when to have a picnic lunch.

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.

The Dairy Market is among Charlottesville's leading food, retail, and entertainment venues. Free parking is available onsite.