One day
Arrive early and take in Piazza Pio II — the cathedral, the Palazzo Piccolomini and its hanging garden — before the crowds. Walk the ramparts behind the palace for the Val d'Orcia view and the little love-named lanes, then graze the Corso's pecorino and food shops and have a pici-and-cheese lunch. In the afternoon, drive the classic Val d'Orcia roads among the cypresses, and return to the ramparts for the sunset.