The towns and villages of the beautiful Orcia valley are perched on hills, high above wide swathes of wheat fields and vineyards. From Pienza, a Pope’s ‘ideal town’, to Montalcino, whose Brunello wine is one of Italy’s most prestigious, with many places you have never heard of in between, all beautiful enough to take your breath away.
Pienza
Named after the Pope who re-created it according to Renaissance principles, Pienza has both splendid architecture and sweeping views of the Val d’Orcia. As the pecorino cheese capital of the region it is also delicious place to stop for a meal. Read more about Pienza here.
Montalcino
Dominated by a vast fortress that now hosts an excellent enoteca offering visitors the chance to taste the area’s prestige red wines, Brunello and Rosso di Montalcino, Montalcino is a charming town with spectacular vistas.
Montisi
Sprawled on a hilltop between the Val d’Orcia and the Crete Senese, Montisi is small village with a large heart. Off the beaten tourist track, it provides a glimpse into the life of a vibrant Tuscan community that knows how to entertain itself.
San Quirico d'Orcia
Located on the ancient Roman Via Cassia, San Quirico‘s medieval walled town centre boasts the beautifully adorned Collegiata of the Saints Quirico and Giulitta, as well as the Horti Leonini gardens, a setting for contemporary sculpture exhibitions.
Radicofani
The town of Radicofani rests at the foot of the hill on which the imposing Rocca fortress was built in 978 and repeatedly restored over the centuries. Known as the headquarters of Ghino di Tacco, Italy’s ‘Robin Hood’, the town honors its history & present.
Author: Dan Wrightson
Dan Wrightson grew up in Tuscany, Italy and has been writing about, sketching and exploring Tuscany and Italy since 1983.
19th Nov 2020 13th Sep 2025