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.
- Distance
- 78 km
- Duration
- 3.5 hrs
- Vehicle
- Car
- Difficulty
- Easy
- Best season
- April – June
- Likes
- 6,210
The route at a glance
Stops along the way
- ●
- 01
- 02
- 03
- 04
- ◆
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 of year to drive the Cypress Trail of Val d'Orcia?
The Cypress Trail of Val d'Orcia is generally best driven April – June. Check local road and weather conditions close to your departure date.
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.