Top 10 cultural & heritage things to do in Charlottesville

1. Four-day Smoky Mountain tour from New York City

Four days of travel by coach — Great Smoky Mountains, Shenandoah National Park, and the Titanic Museum in Pigeon Forge, with bilingual guides and meals included.

2. Self-guided audio tour bundle for Eastern USA road trips

A downloadable audio tour for Eastern USA covering 14 iconic destinations — explore at your own pace without needing cell service.

3. Private custom wine tour of Monticello Wine Trail

Tailored wine tour in a spacious black suburban with a panoramic sunroof, highlighting the Monticello Wine Trail region's best vineyards and dining options.

“I had an excellent experience on the Monticello wine tour. They assisted in creating a personalized itinerary and provided fantastic suggestions based on what I wanted for the day. Our driver, Mark, was friendly and very informed about the region. I would definitely recommend them for a laid-back visit.”— 463reannac

4. Private tour of UNESCO sites: University of Virginia and Monticello

Four hours of guided exploration — the University of Virginia and Monticello, both UNESCO World Heritage sites, with time for refreshments at the Monticello Cafe.

“Jeremiah picked us up right on time in a clean, comfortable vehicle. He was professional, polite, and knowledgeable. When we asked to visit a special spot not included in the itinerary, he kindly made it happen. Thank you, Jeremiah, for your generosity.”— thomasandteresad

5. Charlottesville area private wine tour

Visit three wineries in Virginia’s renowned wine region, exploring the scenic Keswick area with comfortable transportation included.

“Take it easy, interact with the driver, and share your preferences. They have ample experience and can offer guidance and suggestions.”— Julian_W

6. Historic Thomas Jefferson wine tour in Charlottesville

Five-hour tour of Charlottesville's countryside with wine tastings and insights into Thomas Jefferson's historical impact on the region.

“Our tour was truly remarkable. We started with the Rotunda at UVA, and our guide Jeremiah had an impressive grasp of its history. Although it was meant to be a two winery tour, he took us to a third winery to maximize our experience. Jeremiah was not only friendly but also made an effort to ensure we felt valued. He shared insights about local history during our drives, enhancing our understanding of what makes Charlottesville unique. I highly recommend this tour.”— Eric O

7. Self-guided audio tour of Shenandoah National Park

Enjoy a scenic drive on Skyline Drive with a self-guided audio tour of Shenandoah National Park, featuring breathtaking overlooks and insights into the region's history.

“I visited midweek, beginning at Rockfish Gap near Waynesboro, where I stayed overnight for an early start. There was no line to enter the park, and due to the government shutdown, the usual $30 fee was waived. I had learned that I could have obtained a $20 senior annual pass for entry. Make sure to download the park map ahead of time since there's no WiFi and limited cell service. A highlight of my trip was the Action Tours guide I found on TripAdvisor, which cost $16.99. I downloaded it before arriving, and it provided a map and an audio tour of the entire 135-mile drive, detailing points of interest and the trails. It was fantastic and worth the price, with access available for a year after purchase. Driving through was gorgeous, though the speed limit is 35 mph, with sharp curves and wildlife. I spotted deer and various birds, and some tree groves that date back to the park's founding. While traffic was light for a midweek day, there were a few drivers speeding at 55 mph, which posed a risk to wildlife. A semi-truck also sped dangerously, likely making deliveries. Most drivers adhered to the speed limit, allowing time to truly enjoy the stunning scenery transitioning from forest to open meadows. There are several picnic and restroom facilities, including Loft Mountain, Louis Mountain, Skyland, Big Meadows, Elk Wallow, and Dickey Ridge Visitor Center. I look forward to making this drive again and using the Action Tours app once more.”— zstargazer

8. Private wine tour of Charlottesville's vineyards

Flexible tour lasting several hours with a private vehicle — intimate wine tastings at top vineyards near Charlottesville for small groups.

“Williams was very accommodating and took us to three wineries, allowing us to select two that we particularly wanted to experience. He even made an extra stop at our request, which we appreciated. We had a great time with the wine tastings and valued Williams's flexibility. However, given the cost, I was let down by the condition of his vehicle; it was an older minivan that appeared to require some repairs.”— DavidL_R

9. Charlottesville scavenger hunt with interactive remote host

Two to three hours exploring Charlottesville's hidden gems while solving creative clues with a live remote host via your phone.

“The Charlottesville Challenge Scavenger Hunt provided us with an incredible way to discover the city, even if we thought we knew it well. Our favorite part was interacting with locals, as we had fun meeting and interviewing people who live and work there. It encouraged us to step outside our comfort zones and approach strangers, and we were pleasantly surprised by how eager they were to assist us during our scavenger hunt.”— Rakhi_Rodes

10. Charlottesville ghost tour — evening walking exploration

Two-hour walking tour of haunted locations in Charlottesville, featuring local legends and historical tales of tragedy and the supernatural.

“Reubens, our guide, was both friendly and knowledgeable. We appreciated her local stories as well as her personal anecdotes. She facilitated a great conversation among herself and all the guests.”— Alicia R