Driving Tour Val d'Orcia

  • Start Montalcino
  • End Montepulciano
  • Length 70km; one day

Start in the medieval town of Montalcino and follow the SP55 south past vineyard after vineyard planted with the grapes used in Tuscany's most-famous wine, Brunello. You'll soon arrive at the village of Castelnuovo dell'Abata, which looks down on the magnificent Abbazia di Sant'Antimo. After admiring its Romanesque church, continue south on the SP55 and north on the SP323 towards Castiglione d'Orcia. These roads ride a ridge providing sweeping Val d'Orcia views, before twisting down then up through a quintessentially Tuscan landscape: honey-yellow farmhouses set amid rows of cypress trees and vines.

Near Castiglione d'Orcia the crisply geometric lines of the Rocca d’Orcia (also called the Rocca di Tentennano) loom into view. This part-13th-century fortress clings to a limestone spur: follow signs to park beneath it and clamber up for a closer look, both at the castle and the landscape laid out like a living map far below.

Next, the SP323 swoops down amid more panoramic views. Detour to Bagno Vignoni to stroll the fine town square, which frames a vast thermal water-filled basin. Back on the SP323, take the (signed) right turn towards Monticchiello on the SP53 to enter the valley you saw from the high hills. Here a series of minor roads, straight as arrows and lined with cypresses, sweep past farms.

At tiny Monticchiello take in the narrow streets, picturesque squares and panoramic views of the Val d'Orcia; these are best appreciated over lunch on the terrace of Osteria La Porta (note: it’s best to book ahead).

Pick up signs for Pienza; a comfortable cruise that sees the town's duomo-dominated skyline become ever more impressive as you climb nearer. Stop to admire its World Heritage–listed Piazza Pio II, enjoy a coffee or aperitivo at Bar Il Casello or La Terrazza del Chiostro and then head to your final destination, Montepulciano, where there are plenty of accommodation and dining options to choose from.