Why this road
The fastest route skips the valley entirely. This one goes right through it: the Val d'Orcia is a UNESCO World Heritage landscape, shaped over centuries into soft hills of wheat, lone farmhouses on the crests and lines of cypresses along the drives. Between San Quirico and Pienza the road runs high with open views on both sides, and Pienza, a Renaissance town planned by a pope, sits on its edge looking out over all of it.
The route
- ASiena
Leave Siena south on the SR2 Via Cassia. The suburbs fall away quickly and the bare clay hills of the Crete begin.
- 1Buonconvento
A small walled town on the Cassia, at the point where the Arbia meets the Ombrone.
- 2San Quirico d'Orcia
Turn east here towards Pienza. The Renaissance garden Horti Leonini is right by the main street, free and lovely for a short walk.
- 3Pienza
Park below the walls. Walk from Piazza Pio II to the path along the southern wall, the view over the valley to Monte Amiata is the reason you came.
- BMontepulciano
The last climb onto a long ridge. The town is steep, park outside the gates and walk up to Piazza Grande.
Stops worth it
An hour for the piazza, the wall walk and a taste of local pecorino. Mornings are quieter.
Wine cellars under the palaces, the Piazza Grande at the top, and on the way down the church of San Biagio below the town.
Light and the best time
Between San Quirico and Pienza you drive east, so in the late afternoon the sun is behind you and lights the hills, farms and cypresses in front of you. That is the reason to start around 4 pm in spring and autumn. In the evening the view from Pienza's southern wall is lit from the side, with long shadows on the hills. On spring and autumn mornings, fog often lies in the valley at sunrise, worth getting up for.
April to early June is the classic season: green wheat, poppies and soft light. September and October bring golden fields and grape harvest. In July and August the fields are cut and brown and the midday haze is strong. The road is open all year.
By vehicle
A perfect roof-down road: wide views, gentle curves, little heavy traffic.
Relaxed and flowing. Add the side road to Monticchiello from Pienza if you want tighter bends.
Easy all the way, and plenty of farm shops and wineries to stop at.
Fine on these roads. In Pienza and Montepulciano use the larger car parks outside the walls.
Hilly but beautiful. The SR2 can be busy, the stretch from San Quirico to Montepulciano is the nicer part to ride.
Good to know
No toll. All the hill towns have restricted traffic zones (ZTL) in the old centre, park outside and walk. Fuel stations are along the SR2 and near Montepulciano. Many of the famous cypress views are on private farm roads: take photos from the road or public paths and do not drive up private drives.
Route checked against OpenStreetMap on 2 November 2026. Roads, closures and rules change: always check before you go and follow local signs.
Questions
How long does the Val d'Orcia drive take?
About 1 h 45 of driving from Siena to Montepulciano without stops, roughly half an hour more than the fastest road. With Pienza and Montepulciano, plan a full day.
Where are the famous cypress roads in the Val d'Orcia?
Along the SR2 south of San Quirico, around Monticchiello and on many farm drives near Pienza. Some are on private land, photograph them from the road.
Where is the Vitaleta chapel?
On a hill between San Quirico d'Orcia and Pienza, south of the road. You reach it on foot along a gravel track from San Quirico.
When is the best time to see the Val d'Orcia?
Late April to May for green hills and poppies, or October for harvest colours. Early morning fog and late afternoon light are the best moments.