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Morning
Start early in Monteriggioni which takes all of five minutes to walk from one end to the other, but take time to stop in the bar on the piazza for a cappuccino.
Drive on to Volterra starting with San Francesco and its amazing frescoes. On the Piazza dei Priori admire the Palazzo dei Priori (1208–57), the oldest Gothic town hall in Tuscany and the model for most others, including Florence’s Palazzo Vecchio. Tucked into an alcove on the square is the back door of the Duomo – dive inside. Head down Via dei Sarti for the Pinacoteca; continue on this street, which becomes Via di Sotto, lined with several good alabaster workshops, then Via Don Minzoni, where the Etruscan Museum lies.
Afternoon
One block back, on Piazza XX Settembre, Il Sacco Fiorentino is a good spot for a quick lunch before retrieving your car and continuing to San Gimignano getting there just as the tour buses are leaving (but before 4pm in winter, when things close early). Take a quick spin through the Collegiata frescoes before clambering up the Torre Grossa for perhaps the most beautiful panorama in Tuscany.
If you have time after descending – and after pausing at the Museo Civico – head to the other end of town for Sant’Agostino’s frescoes (by 6:30pm). Try to be up on the Rocca for sunset over the towers.
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