Cortona is one of the oldest hill towns in Tuscany and is featured in Francis Mayes book Under the Tuscan Sun, later made into a movie.

Its 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 da Cortona.
Cortona is in the eastern Tuscany, very near the border of the Umbria region and Lake Trasimeno. The closest cities are Arezzo in Tuscany and Perugia in Umbria.Cortona is reachable by train from Rome, Florence, or Arezzo. There are two stations, both below the town, at Terontola-Cortona or Camucia-Cortona.
Cortona can also be reached by bus from nearby towns and villages in Tuscany. If you’re driving, take the A1 Valdichiana exit, then the Siena-Perugia motorway and exit at Cortona-San Lorenzo. Follow signs for Cortona.