🇮🇹 ItalyTuscanyCountryside

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.

Distance

78 km

Duration

3.5h

Vehicle

Car

Difficulty

Easy

Best Season

April – June

Likes

6,210

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Stops along the way

01
Pienza
Pecorino cheese tasting.
02
Cappella della Madonna di Vitaleta
The most photographed chapel in Tuscany.
03
San Quirico d'Orcia
Coffee in the medieval square.
04
Montalcino
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.

Soundtrack for the road

AI-curated mood for this route — open in your favorite player.

Slow countryside roll

Countryside Cruise

Folk · acoustic · bossa nova

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