Discover the surroundings of Siena
Located in the heart of Tuscany, Siena is surrounded by some of Italy’s most well-known areas.
All the areas described below can be visited on half- or full-day excursions.
Val d’Orcia
About 50 km south of Siena lies the Val d’Orcia, one of Italy’s most iconic landscapes. Rolling hills, cypress-lined roads, isolated farmhouses, and historic villages define this area, which is recognized as a UNESCO World Heritage Site because of the harmonious relationship between human settlement and nature.
The Val d’Orcia landscape has inspired painters since the Renaissance and continues to influence contemporary photography and cinema.
The Val d’Orcia region is home to small towns such as Pienza (“the ideal city”), Montalcino, and San Quirico d’Orcia. Each town has a strong local identity. The region is known for its high-quality agricultural products, including olive oil, cheeses, and wines such as Brunello di Montalcino, one of Italy’s most prestigious wines. Its wide-open spaces and slower pace offer a clear contrast to urban life.
More information can be found here: https://en.visitvaldorcia.it/
Image from: https://www.italia.it/en/tuscany/things-to-do/val-orcia
San Gimignano
San Gimignano, located approximately 45 km northwest of Siena, is known for its medieval towers, which symbolized the wealth and power of rival families during the Middle Ages. Fourteen of the original 72 towers built during the Middle Ages are still standing today, giving the town its distinctive skyline. Its historic center is a UNESCO World Heritage Site.
The town is also associated with saffron and Vernaccia di San Gimignano, one of the oldest documented white wines in Italy.
More information can be found here: https://www.sangimignano.com/en/
Image from: https://www.italia.it/en/tuscany/things-to-do/san-gimignano-via-francigena
Chianti
The Chianti region begins just north of Siena and extends across a landscape dotted with vineyards, olive groves, and centuries-old rural settlements. Wine production has been a defining feature of the area since the Middle Ages, and many villages and estates still use traditional methods. The Chianti area is ideal for visitors interested in Tuscan cuisine, wine, and rural traditions.
Chianti Classico wine is identified by the Black Rooster (Gallo Nero), a symbol with roots in medieval legend. The region’s landscape has changed little over time, as agriculture remains its main activity.
More information can be found here: https://www.visitchianti.net/tourist-offices/?lang=en
Image from: https://www.visittuscany.com/en/areas/chianti/
Abbazia di San Galgano
The Abbey of San Galgano is located approximately 30 km southwest of Siena in the open countryside. Founded in the 13th century, the abbey is a great example of Gothic-Cistercian architecture. It is best known for its roofless stone structure that creates a strong visual connection between the building and the landscape.
The Hermitage of Montesiepi, associated with the legend of Saint Galgano and his sword in the stone, which is still embedded in the rock today, stands nearby. Though abandoned in the late Middle Ages, the abbey remains an evocative site reflecting the religious and cultural history of rural Tuscany, offering a distinctive contrast to the region’s towns and villages.
More information can be found here: https://www.fondazionesangalgano.it/
Image from: https://www.italia.it/en/toscana/siena/abbazia-di-san-galgano