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Art and culture in the Val d'Orcia

Discover hills, hamlets and monuments with extraordinary charm

The Val d'Orcia, a fascinating oasis of nature and culture, is dotted with acres of olive groves, oak forests and vineyards. The river that gives the valley its name traces much of the area, touching Radicofani and Sarteano, flowing eastward to the hillsides of Pienza, San Quirico, Montalcino and Castiglione, crossing Monte Amiata and curving around the hills of the Upper Maremma, before merging with the Ombrone. 

Church of Santi Stefano e Degna in Castiglione d’Orcia
Church of Santi Stefano e Degna in Castiglione d’Orcia - Credit: Shutterstock / Ermess

The Val d’Orcia is also home to Bagno Vignoni and Bagni San Filippo, two wonderful thermal towns whose waters, rising from the heart of the volcano, have offered well-being and health remedies for thousands of years, while Castiglione d’Orcia marks the border between the Val d’Orcia and the forests on Monte Amiata. Siena and the Salimbeni family bitterly fought for control of this ancient settlement, formally ruled by the Aldobrandeschi in the 1300s. The village is dedicated to the painter and sculptor Lorenzo di Pietro, known as “Il Vecchietto,” and the centre’s main piazza is home to travertine well built in 1618. Visitors won’t want to miss a tour of the town’s lovely churches, including the Church of Santa Maria Maddalena and the Church of Santi Stefano e Degna. The ruins of two impressive fortresses, Rocca Aldobrandesca and the Tentennano Fortress, are located here as well.

In the hamlet of Rocca d’Orcia, visitors will find the Parish Church of San Simeone (13th century), the Church of San Sebastiano and the Church of Madonna del Palazzo.

A stop in Vivo d’Orcia is sure to be a hit, a tourist hotspot at the foot of Monte Amiata. Not far from the town is the Eremo del Vivo, or Vivo Hermitage, a late-Renaissance building designed by Antonio da San Gallo the Younger. A short walk from Vivo’s acqueduct will take visitors to the Ermicciolo, a small oratory, and the famous “Seccatoi” area, which many experts say is the town’s first ancient settlement.

View of Montalcino from the fortress
View of Montalcino from the fortress - Credit: Shutterstock / Don Mammoser

A visit to Campiglia d’Orcia is highly recommended, a charming town that still retains its original medieval appearance. Near the hamlet, visitors will be the ruins of the Campigliola tower.

Next is Montalcino, known for its production of Brunello, one of the most famous red wines in the world. Montalcino is also a magnificent city for art and dominates a hillside overlooking more than 3,000 hectares of vineyards. Between the Ombrone and Orcia basins sits the Rocca fortress. Built in 1361, the building was constructed to guard the entrance of Montalcino in the direction of Siena. Another worthy stop in the itinerary includes the town hall’s tower, built in the 11th and 12th centuries. Be sure not to miss the Churches of Sant’Agostino and Sant’Egidio (14th century). Visitors will also enjoy the Civic and Diocesan Museum, home to paintings and sculptures from the 13th-19th centuries, as well as several della Robbia terracottas. 

Two winding roads, which snake through the area’s vineyards, will take visitors to Torrenieri, Sant’Angelo in Colle and Poggio alle Mura. From Castelnuovo dell’Abate, you can easily reach the Abbey of Sant’Antimo, one of Italy ’s most famous examples of Romanesque architecture.

Pienza, defined the “ideal city” by Pope Pius II, was recently declared a UNESCO World Heritage Site. In 1458, Enea Silvio Piccolomini decided to transform his hometown into a symbolic Renaissance city. One element of this change was the new Cathedral dell’Assunta, built between 1459 and 1462, which conserves works by some of the most well-known Sienese artists of the time. Nearby, visitors will find the Palazzo Piccolomini, whose loggia offers a wonderful view of the Val d’Orcia, the town hall and the Palazzo Vescovile and its adjoining museum. Don’t miss the medieval Church of San Francesco and the walls of the austere Parish Church in Corsignano, mentioned in historical documents as early as 714.

To the south, visitors will find a road that winds through the hills, leading to the fortified hamlet of Monticchiello, home to various medieval buildings, including a walled fortress and the 13th century Church of Santi Leonardo e Cristoforo, which conserves the interesting remnants of historic frescoes. On the southern border of the valley, visitors should stop in San Quirico d’Orcia, which developed alongside the medieval hamlet of Osenna, before becoming a settlement of Siena in 1256. Still today, the village conserves its historical character.

Radicofani - Credit: Visit Tuscany

Radicofani, on the southern side of the Val d’Orcia, is home to one of the most important fortresses in Tuscany, which dominated the border between the Grand Duchy of Tuscany and the Papal States for centuries. The same site was used by both the Etruscans and the Romans, but fortress dates to around the year 1000. The tower, rebuilt in the 1900s, offers extraordinary views of the Val d’Orcia, Monte Amiata, the Apennines and the Trasimeno and Bolsena lakes.

The churches of San Pietro and Sant’Agata conserve noteworthy collections of della Robbia terracottas and wooden statues, while the historic Palazzo Pretorio is today the town hall. For nature lovers, a stop at the Horti Leonini is recommended, a beautiful garden that was created in 1540 by Diomede Leoni and which today hosts contemporary sculpture. The Palazzo della Posta sits on the ancient via Cassia, a Medici villa that now is used for vin santo production.

If you follow the Cassia southwards, you’ll arrive at Bagno Vignoni, the thermal town that has been known since the Middle Ages for its celebrated piazza d’acqua. On the slope that leads towards the river, visitors will find the Parco dei Mulini—an interesting park that bears witness to plumbing constructions and other similar techniques that were invented in the Middle Ages.