Top Charlottesville Walking Tours

Discover Virginia’s Monticello Wine Trail on a private winery tour in Charlottesville. Create an itinerary with your dedicated guide based on your group’s wine interests and travel in a comfortable, air-conditioned vehicle to each destination. Enjoy guided tours of each vineyard, play indoor games, and savor included snacks during the tour. Purchase wine tastings, if you’d like.

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

Charlottesville has experienced its fair share of turmoil and tragedy, alongside its charming streets and delectable cuisine. From the legend of the enigmatic Moon Ghost who terrorized a local family to the brooding figure of James Madison reported at his beloved Montpelier, the Charlottesville area has been haunted by the shadow of death and destruction for centuries. A bone-chilling stroll at night exposes the enduring existence of the city’s distressing past. This spine-tingling ghost tour will take you to some of the most haunted spots in the city. From the former home of a murdering husband to chilling experiences at a local park, you will delve into the shadows of Charlottesville's murky history. This is a walking tour. We do not ever the private homes or businesses. The duration of the tour is outside and the total tour time is account for us walking from spot to spot.

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.

Your tours are intentionally designed for small groups, allowing us to provide a level of service and attention that larger tour operators simply cannot match. We take the time to understand your preferences, recommend venues that fit your group's personality, and create an itinerary tailored to your occasion. Whether you're celebrating a birthday, anniversary, bachelorette party, date day, or simply enjoying time with friends, every experience is customized around you. What truly makes us different is your concierge-style approach. From the moment we pick you up until we safely return you home, we're focused on the details. We coordinate timing between venues, help keep your day running smoothly, offer local knowledge of Virginia wine country, and provide the flexibility to adjust the day as needed.

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

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