The two unmissable visits from Charlottesville are Monticello and the University of Virginia Academical Village — both Jefferson creations, both UNESCO World Heritage Sites, both genuinely worth the attention the designation implies. Monticello requires a timed ticket and a half-day; the UVA grounds can be walked freely and are most rewarding in late afternoon when the light catches the Rotunda's dome. The Edgar Allan Poe room in the West Range dormitories — where Poe briefly studied in 1826 — is open to visitors and maintained as a small memorial.
The Downtown Mall rewards an unstructured afternoon: good bookshops (New Dominion Bookshop has been here since 1924), the Jefferson Theater for live music, and the Paramount Theater for performances and film. The Ix Art Park, in a converted textile mill off Preston Avenue, has murals, outdoor performance space, and a weekend market worth checking on Saturdays.
For wine, head south or east from the city: Barboursville Vineyards is 30 kilometres northeast; King Family Vineyards, near Crozet, is 20 kilometres west. Most wineries are open for tastings without reservations during the week.