Best 41 things to do in Charlottesville, VA

Build your own private wine or brewery day with pickup in the Charlottesville area

Customize a private Virginia wine-country outing with chauffeur-driven Sprinter service

Choose three South Charlottesville stops for wine, cider, or bourbon

Rent boats or tubes for the day and run your own shuttle and transport plan

Float the Rivanna River with a shuttle back

Self-guided Rivanna paddle with shuttle and Class II ledges

Paddle the Rivanna on a short float with shuttle included

Paddle the Rivanna South Fork with shuttle service and Class I–II rapids

Calm-water paddling with a beach stop on the Rivanna

Exclusive wood-fired sauna and lounge for 90 minutes, ideal for groups up to 10

Private 1-hour horseback ride through vineyard and creek at Cunningham Creek Winery

Ride horseback through Pollak Vineyards with a private guide

Crawl historic cave trails at Grand Caverns with optional climbing and obstacles

Pool access all season in Grottoes, May 23–Sept 7, 2026

Learn cave geology with a certified Park Ranger at Grand Caverns

Watch The Polar Express deep inside Grand Caverns

Private woodland trail ride with mountain views and a Brewpub pint