Top Charlottesville Seasonal & Special Occasions

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.

When you book a tour with, you get the leading tour provided within the the Monticello Wine Trail Region. Depending on group size, day of the week, our group can help get you access to some of the best tables at vineyards, guide you on dining options, and talk you through the history and landmarks of the area.

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 vehicle to each destination. Enjoy guided tours of each vineyard, play indoor games, and purchase wine tastings, if you’d like.

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.

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.

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.

Take the stress out of your family excursion in Charlottesville with this private round-trip transfer from Pantops Shopping Center to the destination of your choice. Skip the guesswork of ride-sharing services or taxis and schedule your pickup in advance, then head straight to your excursion location—including wineries, sights, parks, concerts, or other destinations. Enjoy a few hours of free time to enjoy your family activity before the return trip to the pick-up location or other drop-off point.

Explore Virginia wine country in comfort and style with your own private chauffeur. This experience is perfect for couples or small groups looking to enjoy the best wineries and breweries around Charlottesville without worrying about driving or planning. You'll ride in a luxury SUV and visit 2-4 top wineries or breweries such as: King Family Vineyards Pippin Hill Farm & Vineyard Veritas Vineyard & Winery Highlights: -Private SUV (up to 6 guests) -Door-to-door pickup -Custom itinerary -Local knowledgeable driver Duration: 4-6 hours Why Guests Love It: Stress-free experience Flexible schedule Perfect for special occasions Saturday availability is limited and books quickly.