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Pienza street
Discover the most beautiful towns in the Val d’Orcia
Surround yourself with nature, art and history

The Val d'Orcia is a treasure chest of nature and landscapes, home to some of the most interesting towns in all of Tuscany. In addition to the prestige of the major cities in the Val d’Orcia, the uniqueness of this territory can be found in the presence of many towns, some even fortified, and diffused sites – both civic and holy – which together form a network of exceptionally important historic, artistic, architectural and environmental points of interest.

Here are the must-see towns:

Castiglione d'Orcia
Tentennano Fotress in Castiglione d'Orcia

Castiglione d'Orcia marks the border between the Val d’Orcia and the forests covering Monte Amiata. The centre of the town is the piazza dedicated to the painter and sculptor Lorenzo di Pietro, known as Il Vecchietta, dominated by the ruins of the Rocca Aldobrandesca and the magnificent Tentennano Fotress.

Vivo d’Orcia is one of the hamlets of Castiglione. A stone’s throw away is the Vivo Hermitage, a late-Renaissance palace designed by Antonio da Sangallo the Younger. Starting at the springs of the aqueduct that runs through Vivo, a trail through the beech and chestnut trees leads to the small Ermicciolo church, with its characteristic drying rooms.

Campiglia d'Orcia is also worth visiting, which has preserved its medieval charactersitics, including small streets, narrow staircases and covered walkways. Nearby, you can also find the ruins of the Campigliola tower.

Montalcino
Montalcino

Montalcinofamous for its Brunello wine, is another magnificent art city. Along with its fortress, Palazzo Comunale’s narrow tower, built in the 13th and 14th centuries, is a symbol of Montalcino.

Winding roads through the vineyards lead to Torrenieri, Sant'Angelo in Colle and Poggio alle Mura. From Castelnuovo dell'Abate, you can get to the Abbey of Sant’Antimo, a masterpiece of Romanesque architecture in Italy.

Pienza
Pienza, comissioned by Pius II

Pienza, the “ideal city” commissioned by Pius II, is today a UNESCO World Heritage Site. In 1458, Pius II transformed his home town, commissioning the cathedral, Palazzo Piccolomini, Palazzo Comunale and the bishop’s palace.

To the south, a road winds through the hills all the way to the fortified village of Monticchiello, home to several medieval buildings, a fortress, long stretches of the defense walls and the 13th-century Church of Santi Leonardo e Cristoforo

San Quirico d'Orcia
The Collegiate Church of Santi Quiricio e Giulitta in San Quirico d'Orcia- Credit:  Shutterstock / Andrea Izzotti

San Quirico d'Orcia developed around the medieval village of Osenna. The centre, enclosed by defense walls, is home to the Collegiate Church of Santi Quiricio e Giulitta, Palazzo Pretorio, Palazzo Chigi, Santa Maria di Vitaleta and the Horti Leonini.

Bagno Vignoni
The main square in Bagno Vignoni

Bagno Vignoni, hot springs established in the Middle Ages and famous for the basin in the centre of its main piazza,can be reached along the via Cassia. On the hill sloping down to the river is the Parco dei Mulini, an interesting testament to medieval buildings and techniques using water.

Radicofani
The fortress in Radicofani

Radicofani, on the southern end of the Val d'Orcia, is home to an imposing fortress that for centuries watched over the border between the Grand Duchy of Tuscany and the Holy See. The tower offers an extraordinary view of the Val d’Orcia, Monte Amiata, the Apennines and the Trasimeno and Bolsena lakes.

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