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The nearest airport is at Florence, Amerigo Vespucci Airport, is about 120 km away from Cortona.
By Road
You can hire a car or avail of the numerous private bus services from any of the nearest cities and reach Cortona easily. The drive is a very scenic one.
By Train
You can take a train either on the Rome-Florence line and get off at Terontola or Camucia or the Terontola-Perugia-Assisi-Terni line and get off at Terontola. From either of these stations, you can take a bus or car to Cortona.