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Top Things to Do in Charlottesville

We compared all 5 experiences in Charlottesville so you can choose in minutes — real prices, verified reviews and our editorial picks.

4.8 5 experiences from US$ 270 Free cancellation on most experiences

Things to do in Charlottesville

Charlottesville Wine Tour: 3 Wineries & Private Sedan
Charlottesville Wine Tour: 3 Wineries & Private Sedan★★★★★★★★★★ 4.99 (660)5hYou get picked up in a private sedan, visit three to four Virginia wineries with a guide who knows which tasting rooms are worth your time, and return to Charlottesville after five hours. Lunch is optional and arranged separately. You skip the logistics — the driving, the route planning, the timing — and just show up ready to taste.Is it for me?Book this if you want to taste Virginia wines without driving, coordinating stops, or figuring out which tasting rooms are worth the time — the private guide and sedan handle the route, the timing, and the recommendations, leaving you free to focus on the wine.Travelers' pickMost bookedfrom · per groupUS$ 499View ›
Private Charlottesville Wine Tour: 3 Wineries, No Driving
Private Charlottesville Wine Tour: 3 Wineries, No Driving★★★★★★★★★★ 4.97 (29)5hA private wine tour of Charlottesville visits three carefully selected wineries across the Keswick area in five hours, with a guide, driver and air-conditioned transport included. The route covers the eastside of Virginia's Monticello AVA, passing through the historic Keswick region where Thomas Jefferson once lived. Minimum age is 21; water bottles and a knowledgeable guide are part of the package.Is it for me?Book this tour if you want to taste without driving or planning the route—the guide and driver handle the timing and the roads, so you focus on the wines and the Keswick landscape. The private format means no shared van or group schedule; the day moves at the pace of your group alone.Free cancellationTravelers' pickfromUS$ 270View ›
Charlottesville Wine Tours: Group Transport & Tastings
Charlottesville Wine Tours: Group Transport & Tastings★★★★★★★★★★ 4.36 (28)5hA private wine tour in Charlottesville pairs hotel pickup with transportation to a local vineyard of your choice, a guided tasting experience, and return transport—5 hours total, minimum 3 people, ages 21 and up. The vehicle size adjusts to your group, and the itinerary includes an hour's drive to the vineyard, orientation, 3 hours of tastings and entertainment, then the return trip. Valid ID is required.Is it for me?Book this if your group wants to taste without anyone driving—the private vehicle and fixed 5-hour schedule mean you show up at your hotel at the agreed time and the rest is arranged. It suits couples, small celebrations, and teams who want the tasting experience without the logistics of finding the vineyard, parking, or coordinating who's driving back.Free cancellationTravelers' pickfrom · per groupUS$ 280View ›
Private Wine Tour Charlottesville: Custom Itinerary in Suburban
Private Wine Tour Charlottesville: Custom Itinerary in Suburban★★★★★★★★★★ 4.78 (18)5hA private wine and brewery tour in Charlottesville puts you in a luxury Chevrolet Suburban with a knowledgeable guide who builds the day around your preferences—visit 3–4 wineries, breweries, cideries or distilleries within the Monticello Wine Trail Region at your own pace. The itinerary is entirely customized; you choose which venues to visit and how long to stay at each. A live English-speaking guide is included, along with transportation, chilled water, and gratuities; tasting fees and alcohol are separate.Is it for me?The five-hour window is what makes three to four tastings fit into one afternoon without the day feeling like a checklist—you move at a conversational pace, and the guide handles the route so you're not navigating between stops.Instant confirmationfrom · per groupUS$ 549View ›
Charlottesville Wine Tour: Jefferson & Barboursville tastings
Charlottesville Wine Tour: Jefferson & Barboursville tastings★★★★★★★★★★ 4.80 (5)5hA 5-hour guided wine tour in Charlottesville pairs tastings at Jefferson Vineyards and Barboursville Vineyards with a self-guided walk through the Rotunda and Academic Village, where Thomas Jefferson's influence shaped the region. The tour includes private transportation, an air-conditioned vehicle, water bottles and a knowledgeable English-speaking guide; food and beverages beyond the tastings are on your own.Is it for me?Five hours leaves room for a leisurely afternoon—the self-guided Rotunda walk, two full tastings, lunch if you want it, and time to explore the Barboursville ruins—without eating the whole day. If you need to fit other Charlottesville stops into your schedule, this tour's fixed duration and private transport mean you're not waiting for a group or a shuttle to move on.Free cancellationTravelers' pickfromUS$ 270View ›
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