Renaissance art, Chianti vines & cypress roads
This is leg 3 of 3, the final leg.
Travel leg · Tuscany Hill Towns
Siena to Val d'Orcia
Siena and Val d'Orcia sit about 39 km (24 mi) apart in a straight line, with Val d'Orcia to the south-east. It is leg 3 of 3 on our Tuscany Hill Towns itinerary, a 7-day trip. Here is how long it takes by car, what to see on the way and where it fits in a real itinerary.
- Straight-line distance
- 39 km · 24 mi
- Est. road distance
- 47–54 km
- Est. drive time
- 35 min – 1 h
- Direction
- Heading south-east
- Curated routes
- 1 itinerary
Road distance is estimated as 1.2–1.4× the straight line; drive time assumes average speeds of 50–80 km/h with no stops or traffic. These are rough estimates — check a maps app for the actual route.
Ways to get there
We don't have live routing data, so the figures below are labelled estimates built from the straight-line distance. Use them to plan the day, then confirm in a maps app.
By car
Most travelers on our Tuscany Hill Towns itinerary do this leg by car. We estimate 47–54 km (29–34 mi) of road and 35 min – 1 h behind the wheel, so check live traffic before you set off.
By train
Our Tuscany Hill Towns guide also mentions trains for parts of the trip. Whether a direct train links Siena and Val d'Orcia depends on the line — check timetables.
Rail or a short ride connects Florence and Siena, but the countryside rewards a rental car. Chianti and the Val d'Orcia are made of small roads and villages, so driving gives you freedom. Pick a designated driver if wine tastings are planned.
Worth stopping for
Picks from our curated guides at both ends.
When you arrive in Val d'Orcia
Spend 2–3 days based at an agriturismo: hill towns, wine cellars, thermal springs and cypress-lined roads.
Pienza
Renaissance town rebuilt by Pope Pius II, with pecorino shops and valley views.
Trattoria Latte di Luna
Pienza trattoria known for roast suckling pig and pici.
Cantine Contucci
Ancient cellars under Piazza Grande, making Vino Nobile for centuries.
Cappella della Madonna di Vitaleta
Small chapel among cypresses, one of Tuscany's most photographed views.
Bagno Vignoni
Village whose main square is a thermal pool; soak in the free pools below.
Montepulciano
Hilltop town with Renaissance palaces and wine cellars beneath them.
Before you leave Siena
Stay one night to see the Campo after day-trippers leave; one full day covers the cathedral and museums.
On this curated route
Where Siena → Val d'Orcia sits in the full itinerary. Highlighted stops are this leg.
Going the other way? Val d'Orcia to Siena is the same 39 km in a straight line, heading north-west. Reverse directions in Google Maps ↗
Siena to Val d'Orcia: questions travelers ask
How far is Siena from Val d'Orcia?
Siena is about 39 km (24 mi) from Val d'Orcia in a straight line, with Val d'Orcia to the south-east. By road, we estimate 47–54 km (29–34 mi), or 1.2–1.4 times the straight line. Check a maps app for the exact route.
How long does it take to drive from Siena to Val d'Orcia?
An estimated 35 min – 1 h, assuming 47–54 km of road at average speeds of 50–80 km/h with no stops or traffic. It is not a routed time, so check a maps app on the day.
Which itineraries include the trip from Siena to Val d'Orcia?
Our Tuscany Hill Towns itinerary includes this leg. Tuscany Hill Towns runs about 7 days across 4 stops, best in Apr – Jun, Sep – Oct.
Getting to Siena
- Chianti to Siena 29 km
Guides for both ends
- Siena travel guide
- Siena weather best time to visit
- Val d'Orcia travel guide
- Val d'Orcia weather best time to visit
Val d'Orcia by month
Plan Siena → Val d'Orcia with your crew
Add this leg to a shared itinerary, poll the group on where to stop, split fuel and tickets, and keep everyone's packing list in one place in TripsCircle.