Val d’Orcia slow road
Cypress avenues, Montalcino’s Brunello and Renaissance Pienza in a UNESCO landscape.
- Distance
- 59 km (37 mi)
- Driving
- 0 h 49 min
- Suggested days
- 3
- Stops
- 4
- Countries
- Italy
- Updated
- August 24, 2026
At a glance: 3-day road trip of about 59 km (37 mi) with 4 stops, from Siena to Pienza. About 0 h 49 min of driving in total.
Route description
Leave Siena, with its shell-shaped Piazza del Campo and striped cathedral, on the SR2, the old Via Cassia, and head south into the clay hills of the Crete Senesi. Near Buonconvento, turn off and climb to Montalcino, a hilltop town with a 14th-century fortress and the cellars where Brunello di Montalcino is made and poured.
Below Montalcino the Romanesque abbey of Sant’Antimo sits alone in the fields and is worth the short detour. Back on the SR2 near San Quirico d’Orcia, you reach the heart of the Val d’Orcia, a UNESCO landscape of rolling fields and cypress avenues; the best-known group of cypresses stands right beside the road, with space to pull over.
The last stop is Pienza, rebuilt in the 15th century by Pope Pius II as an ideal Renaissance town, with views from its walls over the whole valley and pecorino cheese in every shop. Spring and autumn bring the best light and fewer crowds. Historic centres here are limited traffic zones, so park outside the walls, and keep motorhomes off the white gravel roads that wind between the farms.
Stop-by-stop itinerary
In driving order. Distances are estimates between consecutive stops.
- 1Start
Siena
Italy - 240 km
Montalcino
Italy - 312 km
Val d'Orcia cypresses
ViewsSan Quirico d’Orcia, ItalyRolling Tuscan hills lined with cypresses, a UNESCO landscape. The best-known cypress group is beside the SR2.
- 48 km
Pienza
Italy