Late spring and early autumn are the best times. May and September give long, mild days with quieter streets and the surrounding countryside at its prettiest — wildflowers in May, the autumn harvest in October. July and August are hot, busy, and full of group tours following Under the Tuscan Sun.
The Cortona Mix Festival in mid-July brings a week of live music to the squares. Sagra della Bistecca, the August beef festival, is the town's largest culinary event — long communal tables in the public gardens and an open-air grill working for hours. Winter is very quiet but many restaurants close.