Buongiorno,
Arezzo train station is at the base of the city - and from there it is a steady climb to the top of the hill. However, I believe taken in small pieces - stopping and enjoying the various points of interest along the way it can be very do-able. Sometimes the climb is barely noticeable...and sometimes it is a bit more steep….but personally, totally worth it. I love this city and all of its hidden treasures.
Have a look at this article for a suggested walking itinerary. The steepest part is from Piazza San Francesco to the Cathedral. (but there are so many cute little bars along the way...you might be tempted to stop at each one

)
http://www.discovertuscany.com/arezz...ur-arezzo.html
I also suggest you look at Castiglione del Lago and Chiusi - both to the south of Cortona and both accessible by train.
Buon Viaggio,
Donna Denise
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