Born as a fortified castle in the eleventh century, Torrita di Siena developed with the specific function of a military outpost, a sentinel standing guard over the Sienese borders against the frequent threats from Florence and nearby Montepulciano. This defensive vocation is still noticeable today while walking along the perimeter of its ancient 14th-century walls, punctuated by massive square towers and historic gates, which enclose a historic center that has remained remarkably intact in its medieval charm. Passing through the village gates, the austere military architecture gives way to a surprising artistic wealth. The town’s beating heart is Piazza Matteotti, dominated by the 13th-century Town Hall and the Collegiate Church of Saints Flora and Lucilla. It’s right inside this religious building that one of the greatest Renaissance treasures in the Sienese land is hidden: the marble lunette of the Blood of Christ, a very refined work attributed to the genius of Donatello.

Perched on a green hill, Trequanda marks the border between the Crete Senesi and the Val di Chiana, offering a spectacular view of a surprisingly beautiful countryside. Its definitive urban development dates back to the Middle Ages, becoming a fief of the powerful Cacciaconti family before being absorbed under the direct control of the Republic of Siena. This past as a contested castle is still carved into the stone of the majestic Cacciaconti Castle, which towers with its imposing crenellated cylindrical tower guarding the town, and in the remains of the ancient walls that enclose narrow, quiet streets. The real artistic jewel of the town is the Church of Saints Peter and Andrew. Its 14th-century facade is a unique architectural masterpiece throughout Tuscany, featuring an enchanting two-tone checkerboard pattern where ochre tuff and white travertine blocks alternate geometrically. Trequanda’s identity also comes through strongly in its craftsmanship, which reaches its peak in the village of Petroio, internationally renowned for centuries of terracotta work made using local clay from the Crete region. The Terracotta Museum is definitely worth a visit.

The nature of Castelnuovo Berardenga is a scenic landscape hinge, a magical place where the dense woods and geometric hills of Chianti Classico gently slope towards the lunar landscapes and gullies of the Crete Senesi. The area is an endless chase of excellent vineyards and silvery olive groves, interrupted only by long and iconic cypress-lined avenues. The view stretches from the wooded hills of Chianti to the open, rolling horizon of the nearby Val d’Orcia. Castelnuovo Berardenga takes its name from the Berardenghi, a noble family of Frankish origin that ruled this area from the tenth century. The current town was founded in 1366, when Siena built a ‘new castle’ to protect its borders from attacks by Florence. For centuries, the village was a frontline battlefield until it became part of the Grand Duchy of Tuscany. Even today, the shape of the historic center shows its military past, dominated by the clock tower that used to be the castle’s watchtower.

Located in the Crete Senesi along the Via Francigena, Monteroni d’Arbia developed from the 13th century as an agricultural hub and a stop for pilgrims, managed by Santa Maria della Scala of Siena. Without a military focus as a town, it preserves its greatest historical masterpiece a short distance from the center: the Grancia di Cuna. This impressive red-brick complex is one of the rare European examples of a fortified medieval farm, built as a secure granary to protect the food reserves of the Republic of Siena.

Not far from Siena and rich in water and woods, Sovicille was a highly sought-after territory and a key outpost for the Republic of Siena. For this reason, it suffered many attacks and looting by the Florentines, until peace arrived with the Grand Duchy of Tuscany. Today, this area boasts one of the largest concentrations of castles and Romanesque parish churches in the entire region. Among these, the most famous is the Pieve di Ponte allo Spino, a twelfth-century masterpiece with beautiful capitals carved by French and Norman masters.

Radicondoli proudly stands on a wild hill, where the province of Siena merges with the Metalliferous Hills. Of Etruscan-Roman origin, the village reached its peak in the Middle Ages as a powerful castle of the Alberti counts of Mangona. This wooded fortress was long contested between the Republic of Siena and the bishops of Volterra, before finally coming under Siena’s control in 1230. The heart of the historic center is home to the 16th-century Collegiate Church of Saints Simon and Jude, which houses valuable paintings from the Sienese school by Pietro di Domenico and Alessandro Casolani. Just outside the village, you can find the evocative ruins of the Monastery of San Francesco and the Romanesque Church of San Giovanni Battista in Anqua, located within a historic noble estate. The surrounding environment is the most untouched part of the Sienese itinerary, dominated by dense forests of holm oaks, oaks, and cork trees teeming with wildlife. The real standout, though, is the geothermal activity: being close to the borax area fills the landscape with natural steam vents and vapors coming straight out of the rocks, giving the area a magical, almost primordial atmosphere.