It’s all uphill to Cortona’s defenses, built in 1556. Handily, or ironically, the torturous, stepped ascent is enlivened by 15 mosaics depicting the Stations of the Cross by Cortonese Futurist Gino Severini (1883–1966). By the second time Christ falls, you'll feel like doing the same, though you can pause for a restorative drink at the bar by the Basilica Santa Margherita. The views from the four surviving bastions reward the climb, extending all the way across the Valdichiana to Montepulciano, south into Umbria toward Lago Trasimeno, and north toward Arezzo and the colossal Monte Amiata.