Bevagna, Umbria
Unusual for being a medieval town not on a hilltop, Bevagna has a number of worthwhile charms. Most notable is the Mercato delle Gaite, a medieval festival that showcases medieval arts and occupations.
Where to eat: Trattoria di Oscar elevates Umbrian food to new and dizzying heights. And Scottadito is excellent for sampling meats (both grilled and cured) of the region.