Cortona is one of the oldest hill towns in Tuscany and is featured in Francis Mayes book Under the Tuscan Sun. Cortona's medieval streets are pleasant to wander and you'll be rewarded with fabulous views of the countryside along the medieval town walls. Cortona has remnants of its pre-Roman Etruscan past, Renaissance artists Luca Signorelli and Fra Angelico, and Baroque artist Pietro di Cortona.