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SR2

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.

  1. 1

    Siena

    Italy
    Start
  2. 2

    Montalcino

    Italy
    40 km
  3. 3

    Val d'Orcia cypresses

    ViewsSan Quirico d’Orcia, Italy

    Rolling Tuscan hills lined with cypresses, a UNESCO landscape. The best-known cypress group is beside the SR2.

    12 km
  4. 4

    Pienza

    Italy
    8 km