Best 37 things to do in Charlottesville, VA

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

Calm-water paddling with a beach stop on the Rivanna

Wood-Fired Sauna, Cold Tubs, and Riverfront Community

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

Plan a private, driver-led tasting route through Charlottesville’s local drink scene

Build your own three-stop Afton beverage outing with round-trip transportation

Build your Route 151 itinerary with four flexible tasting stops

Build a Route 231 day with three winery, brewery, or dining stops

Build your own four-stop Crozet beverage route with round-trip transportation

Explore Keswick vineyards on a private guided ride with mountain views

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

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

Float the James at dusk with live acoustic music and charcuterie

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

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

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