We went to Cortona for the day when we were in Tuscany. Surprisingly I had never been there before. I went to Perugia uni when I was 18, and Perugia is just 30 miles away. Given it is up on top of a mountain and I went everywhere by train when I was a student, I guess Terontola was as close as I ever got. What an omission! Beautifully quaint, it is built on top of a hill with spectacular views of Trasimeno and the whole Tuscan and Umbrian plain.
And it wasn't even knee-deep in tourists. Parking was free just outside the city wall too. You don't find that often! I'd definitely recommend it if you have a couple of hours to kill.