Arezzo is pleasant year-round but has two dates worth planning around: the Giostra del Saracino jousting tournament (third Saturday of June, and first Sunday of September), when the town fills with costumes and medieval pageantry, and the first weekend of each month for the Fiera Antiquaria antique market.
Summer (June–August) is warm and busy but significantly less crowded than Florence or Siena. Spring and autumn are the best seasons for the frescoes and the general atmosphere. Winter is quiet, the light is good, and the Piazza Grande loses none of its character in cold weather.