06/10/2026
Val d’Orcia’s Most Beautiful Villages — 10 Places You Shouldn’t Miss 🇮🇹
There are parts of Tuscany that feel almost designed for a painting, and Val d’Orcia is one of them. Rolling hills, cypress-lined roads, medieval stone villages, vineyards and tiny thermal towns all sit surprisingly close together, which makes this one of the best areas in Tuscany to explore slowly.
1. Pienza
Probably the most famous village in Val d’Orcia, and for good reason. Its Renaissance centre is beautiful, but some of the best moments come from the streets at the edge of town, where terraces open onto huge views across the valley. This is also the place to try Pecorino di Pienza.
2. Montalcino
A hill town surrounded by the vineyards that produce Brunello di Montalcino. Walk up to the fortress, explore the narrow streets and stop at one of the viewpoints overlooking the countryside.
3. San Quirico d’Orcia
One of the places I would never skip. It is quieter than Pienza, with medieval streets, the Collegiate Church and the beautiful Horti Leonini gardens. Several of the classic cypress landscapes you see in photographs are also nearby.
4. Bagno Vignoni
One of the most unusual villages in Tuscany. Instead of a normal central piazza, the heart of the village is occupied by a large thermal-water basin that has been here for centuries.
5. Monticchiello
Small, stone-built and beautifully positioned above the valley. Monticchiello has preserved much of its medieval character, and the roads around it offer some of the most recognisable Val d’Orcia views.
6. Castiglione d’Orcia
Less visited than Pienza or Montalcino, which is exactly part of its appeal. Its stone streets climb through the old centre, with Rocca di Tentennano dominating the surrounding landscape.
7. Rocca d’Orcia
Just beside Castiglione, this tiny settlement feels dramatically medieval. The fortress above it is the reason to come, especially for the views over the valley.
8. Vivo d’Orcia
A very different side of Val d’Orcia. Sitting on the slopes of Monte Amiata, it is greener, cooler and more wooded than the open landscapes around Pienza. It is a good stop if you want something less obvious.
9. Bagni San Filippo
Known for its natural hot springs and white mineral formations hidden among the trees. The most famous section is the enormous calcium formation often called the White Whale.
10. Radicofani
Farther south and much more dramatic than many people expect. The huge fortress rises above the town and can be seen from miles away. From the top, the views across southern Tuscany are extraordinary.
You do not need to rush through all ten in one day. Val d’Orcia is at its best when you leave time for the roads between the villages, stop at viewpoints, have a long lunch and let the landscape become part of the trip.
If I had to choose only five for a first visit, I would start with Pienza, Montalcino, San Quirico d’Orcia, Bagno Vignoni and Monticchiello.
