Cortona's pleasures are concentrated in the historic centre — the Piazza della Repubblica, the two excellent museums on Piazza Signorelli, the medieval churches, and the steep streets climbing toward the Medici fortress at the top of the hill. The town is small but not flat; a half-day of slow walking covers most of what matters, but the views and the wine usually keep visitors longer.
Outside the walls, the Etruscan tombs scattered through the valley below and the Renaissance church of Santa Maria delle Grazie al Calcinaio are worth the short drive.