The closest airport is Florence, but for continental flights is Rome.

Cortona can be easily reached either by car or by train, being served by the Autostrada del Sole (Valdichiana exit), State Road SS 71 and the Milan-Florence-Rome railway.

By train:
Direct train Milan-Firenze-Roma (see time tables for Rome-Cortona and Milan-Cortona connections:
Terontola-Cortona railway station (194 km from Rome, 122 km from Florence)
Camucia-Cortona railway station
The Terontola station is 11 km from Cortona and the Camucia station is 5 km from Cortona. There is a bus service to Cortona from both stations.

By car:
Autostrada del Sole (State Highway green on the map above):"Valdichiana" Exit. Upon exiting the highway, take the Siena-Perugia State Road and continue towards Perugia. There are 3 possible turn-offs for Cortona: Cortona via Manzano, Cortona via Laurentana and Cortona via Strada Statale 71 (State Road 71). In this latter case, at Camucia there is a deviation for Cortona and Città di Castello (the Umbran-Cortonese Province Road).