For who travels by train in Castiglion Fiorentino there is a pretty efficient train station from which is possible to go to Arezzo, Firenze, Pisa Aeroport, Florence AirportAssisi, Orvieto and Rome even for a day trip. For a dinner in Cortona the cab fee to Casa Traquandi at night  is about  €20. Last but not least the beautifu Perugia ( famous also for the jazz festival Umbria jazz) and Spoleto and Foligno