Day one of a local travel guide's proximity-organized Monticello Wine Trail weekend, grouping four wineries just south of Charlottesville: begin southwest at Pippin Hill in North Garden, then the Carter Mountain-area cluster below town (Blenheim, Gabriele Rausse, Jefferson), in the guide's published order. The three Charlottesville-address stops carry town-centroid coordinates, so the map labels them approximate. The guide's later days pair these with wineries not on this trail's roster (Early Mountain, Veritas), which are omitted here.
Monticello Wine Tour & Coach Co. ↗ — Local private 5-hour wine and brewery tours for up to 14 guests in Mercedes Sprinter vans/Suburbans; no pickup fee within Charlottesville, Albemarle County or Wintergreen. source ↗
Blue Ridge Wine Excursions ↗ — Custom Charlottesville/Monticello wine tours since 2009, with sedans, SUVs, Sprinter vans and mini-coaches/party buses. source ↗
Each winery card links to its website and any social profiles we could verify. A greyed icon means
we have no verified link for that platform — not a broken link.