Cypress-lined hills and Renaissance hill towns south of Siena. That is what Val d'Orcia promises, and it delivers. At about 50 miles (80 km), it is a drive best taken slowly, over 1–2 days, with time to pull over whenever the view demands it on the way from Siena to Montepulciano.
Open this route in XCRSNSetting out from Siena
Start early, with a full tank and a loose plan. Siena is where the road begins, and the first miles set the rhythm for everything that follows.
The first big moment is Cappella della Madonna di Vitaleta. Give it the time it deserves; it is why many people make this trip at all.
Along the way
The road strings together San Quirico d'Orcia and Pienza. Each one makes a natural break, and Pienza sits close to the middle if you want to split the drive with a night's sleep.
Do not miss Pienza.
Arriving in Montepulciano
Save energy for the final stretch: Montepulciano wine is still ahead.
By the end you will have seen Cappella della Madonna di Vitaleta, Pienza and Montepulciano wine, and you will understand why Val d'Orcia belongs on any list of great drives.
When to go and how to pace it
The best time to drive it is April–June or September–October. Plan on 1–2 days so the drive never feels rushed.
Check route weather and fuel stops on the Plan tab before you go.
XCRSN prices fuel for every leg in the local currency, finds stops along the way and books overnights near each town.
