Cypress Trail of Val d'Orcia
Postcard Tuscany distilled into a single afternoon. Cypress-lined roads thread between Pienza, Montalcino and a half-dozen forgotten chapels. Stop often. The light here changes by the minute.
The Cypress Trail of Val d'Orcia is a 78 km countryside drive in Tuscany, Italy. It runs from Pienza to Montalcino in about 3h 30m of driving. Highlights include Cappella della Madonna di Vitaleta and San Quirico d'Orcia. Best driven April – June; rated easy difficulty.
- Road length
- 78 km
- Duration
- 3.5 hrs
- Vehicle
- Car
- Difficulty
- Easy
- Best season
- April – June
- Likes
- 6,210
Road length is the scenic route itself — your actual door-to-door driving distance depends on where you start and which stops you take.
Best time to drive
April – June
Expect more visitors in July–August peak season; shoulder months (May–June, September) are usually quieter and often offer better light.
General guidance only — always confirm local road and weather conditions before departure.
How many days for Cypress Trail of Val d'Orcia?
This route fits comfortably in a single day.
With 4 recommended stops along the way, you can still take it leisurely and enjoy the scenery.
Estimate based on total driving time — actual pace depends on stops, traffic, and breaks.
The route at a glance
Stops along the way
- ●
- 01Open in MapsPienza
Pecorino cheese tasting.
- 02Open in MapsCappella della Madonna di Vitaleta
The most photographed chapel in Tuscany.
- 03Open in MapsSan Quirico d'Orcia
Coffee in the medieval square.
- 04Open in MapsMontalcino
End with a Brunello tasting.
- ◆
Travel tips
- ★Order the pici al ragù in Pienza.
- ★Sunrise reveals the hills in mist.
- ★Avoid August — too hot, too crowded.
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Frequently asked
How long does it take to drive the Cypress Trail of Val d'Orcia?
The Cypress Trail of Val d'Orcia takes about 3h 30m of driving non-stop to cover its 78 km. Actual trip length depends on how often you stop at viewpoints and towns along the way.
How long is the Cypress Trail of Val d'Orcia?
The Cypress Trail of Val d'Orcia is 78 km long, running from Pienza to Montalcino.
When is the best time to drive the Cypress Trail of Val d'Orcia?
Best driven April – June. Expect more visitors in July–August peak season; shoulder months (May–June, September) are usually quieter and often offer better light.
Is the Cypress Trail of Val d'Orcia hard to drive?
The Cypress Trail of Val d'Orcia is rated easy difficulty. It is classified as a countryside.
What are the main stops on the Cypress Trail of Val d'Orcia?
The route runs from Pienza to Montalcino, with key stops including Cappella della Madonna di Vitaleta, San Quirico d'Orcia.
Where is the Cypress Trail of Val d'Orcia?
The Cypress Trail of Val d'Orcia is located in Tuscany, Italy. It runs between Pienza and Montalcino.