THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend five relaxed hours driving the eastside of Charlottesville to three curated wineries in the Monticello AVA. Expect guided tastings, picnic lawns, and small‑batch bottles that showcase Virginia’s Piedmont terroir.
Spend five relaxed hours driving the eastside of Charlottesville to three curated wineries in the Monticello AVA. Expect guided tastings, picnic lawns, and small‑batch bottles that showcase Virginia’s Piedmont terroir.
Book with Ole Crow Tours
Book directly with Ole Crow Tours for the best rates and real-time scheduling.
Reserve NowVerified experiences and guided adventures in the surrounding area.
Operated by Ole Crow Tours · Charlottesville, Virginia
You step into an air-conditioned van outside downtown Charlottesville and the Piedmont unfurls—low ridgelines, hedgerows, and vineyard rows that crouch along gentle slopes. The guide eases you through country lanes toward Keswick; sunlight picks out limestone outcrops and the grasses hum as if urging you on. Over the next five hours you visit three distinct tasting rooms, each staged to highlight Virginia’s Monticello AVA and the people who coax flavor from clay and loam.
easy.
5 hours.
Suitable for all fitness levels; mostly seated in a vehicle with short walks at each winery
The private tour is approximately 5 hours long with three winery visits of roughly 60–100 minutes each.
Yes—private, air-conditioned transportation is included and pickup can be arranged within the Charlottesville area.
Most participating wineries sell bottles on site and can often ship purchases; ask staff about vintages and shipping policies during your visit.
Infants and small children can ride in strollers and infant seats are available; short, level walks at tasting rooms make the tour generally accessible but check specific mobility needs with the operator.
The tour runs through the Monticello AVA and Keswick area, lands shaped by 18th–19th century estates and the wine‑interested legacy of Thomas Jefferson.
Many vineyards here practice sustainable viticulture and encourage visitors to stay on paths; carry out picnic waste and avoid trampling vines to protect soils and habitat.
Ole Crow Tours operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Ole Crow Tours
Book directly with Ole Crow Tours for the best rates and real-time scheduling.
Reserve Now