Montepulciano's main street – called in stages Via di Gracciano, Via di Voltaia, Via dell'Opio and Via Poliziano – climbs up the eastern ridge of the town from Porta al Prato and loops to meet Via di Collazzi on the western ridge. To reach the centre of town (Piazza Grande), take a dog-leg turn into Via del Teatro.

　　In Piazza Savonarola, up from the Porta al Prato, is the Colonna del Marzocca, erected in 1511 to confirm Montepulciano's allegiance to Florence. The late-Renaissance Palazzo Avignonesi is at No. 91 Via di Gracciano nel Corso. Other notable buildings include the Palazzo di Bucelli at No. 73 (look for the recycled Etruscan and Latin inscriptions and reliefs on the lower facade) and Palazzo Cocconi at No. 70.

　　Continuing uphill, you'll find Michelozzo's Chiesa di Sant'Agostino, with its lunette above the entrance holding a terracotta Madonna and Child, John the Baptist and St Augustine. Opposite, the Torre di Pulcinella, a medieval tower house, is topped by the town clock and the hunched figure of Pulcinella (Punch, of Punch and Judy fame), which strikes the hours. After passing historic Caffè Poliziano, the Corso continues straight ahead and Via del Teatro veers off to the right.