Best 25 things to do in Charlottesville, VA

Customize a private wine and brewery day trip with Sprinter van transport

Customize a private Charlottesville wine tour with pickup included

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

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

Build your own Charlottesville wine and brewery route with a private driver

Private guided horseback ride through Veritas Vineyard in 90 minutes

Ride horseback through Pollak Vineyards with a private guide

Take a private guided horseback ride with time for a cider tasting after

Ride Chiswell Farm trails, then head to the tasting room

Ride a private guided trail through Keswick Vineyards, then enjoy a complimentary glass

Private backcountry horseback ride on wooded trails with mountain viewpoints

Rent a John E Painter Park shelter from 8am to dusk for your group

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

Cave with a guide in dark Fountain Cave with route options

Tackle a challenging 3–4 hour caving expedition in Fountain Cave

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

Walk Grand Caverns by candlelight and dig into its 1800s history

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

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

Explore Keswick vineyards on a private guided ride with mountain views

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