10 small towns to visit near Siena

In this post we’ll explore 10 small towns in the Siena surroundings: some of them are off the beaten path, others more famous.


1. Montepulciano

Located 66 kilometres from Siena, Montepulciano is nestled between the Val D’Orcia and the Val di Chiana. Montepulciano is a medieval village known worldwide for being the “jewel of the 1500s” due to its impressive Renaissance art and architecture. It is also famous for its Vino Nobile, as well as other local specialties. The main square is called Piazza Grande and boasts the great tower and Gothic façade of the Palazzo Comunale (Town Hall) and the Cathedral of Santa Maria Assunta, which dates back to 1619. Don’t miss the view of the Tuscan countryside with the beautiful church of the Madonna di San Biagio


2. Monteriggioni

Monteriggioni is a medieval walled town built on a hill by the Sienese people in the thirteenth century. The main characteristic of the village is the magnificent 10-meter exterior walls with fourteen towers on square bases, visible from far away. Monteriggioni was a major stop along the Via Francigena and the name of one of the gates points toward this history: Porta Franca. Another gate is the Porta San Giovanni: no matter which one you choose, you are already in the heart of the village. The main square is called Piazza Roma and features the Church of Santa Maria Assunta in Romanesque and Gothic style.


3. San Gimignano

San Gimignano, about 40 kilometres away from Siena, is a walled village that UNESCO designated a World Heritage Site in 1990. San Gimignano flourished in the thirteenth and fourteenth centuries and used to boast 72 towers, which is why it is also known as the “Manhattan of the Middle Ages”. 15 towers still stand today. You can climb the Torre Grossa and visit its Civic Museum; you can visit the Collegiata (Romanesque ex-cathedral), the Church of Sant’Agostino with a wonderful 15th-century fresco cycle by Benozzo Gozzoli and, if you are brave enough, the torture museum.


4. Torrita di Siena

Torrita di Siena is an ancient village situated on the western slopes of the Val di Chiana, about 40 kilometres southeast of Siena. Once you reach Piazza Giacomo Matteotti, the central square, take a look at the Town Hall, the ancient cistern and a Romanesque church with a single nave, named after Saints Flora and Lucilla. If you visit Torrita around March 19, you’ll come across the donkeys’ race known as “Palio dei Somari”


5. MontalcinoT

The hill town of Montalcino, completely encircled by fortified walls, is located in the Val d’Orcia, a few kilometres from Pienza and the Crete Senesi, not far from Monte Amiata. It has remained practically unchanged over the centuries, with its 13th-century defensive walls and its historical centre dominated by the 14th-century fortress. You can visit the neoclassical-style cathedral dedicated to San Salvatore and Montalcino main square with the Town Hall and a few cafes, bar and restaurants. There are many other things to see, but don’t forget to taste the local wine!


6. Buonconvento

The medieval village of Buonconvento is located about 25 kilometres southeast of Siena, just a 25 minute train ride from Siena, and the train station is a short walk from the historic centre. It was named one of the most beautiful towns in Italy (I Borghi più belli d’Italia). The Via Francigena passes through here, too. You can visit the Museo della Val d’Arbia (Val d’Arbia Museum) and the Museo di Arte Sacra (the Museum of Sacred Art), Palazzo Ricci, the church of San Pietro e Paolo (Saint Peter and Saint Paul) and the Oratorio di San Sebastiano (the Oratory of Saint Sebastian).



Around 25 kilometres away from Siena lies the village of Castellina in Chianti, which has ancient origins, evident in the Etruscan tombs in Montecalvario, just outside the town. Its location at the intersection of four areas of Chianti made this city a key strategic location between Florence and Siena. You can visit the imposing fortress, which overlooks the central square, and the charming Via delle Volte, a walkway through the village that offers views of the surrounding landscape. You can also see the Church of St. Salvatore and the Archaeological Museum of Chianti.


8. San Quirico d’Orcia

San Quirico is a walled village situated in the Val d’Orcia, about 35 kilometres southeast of Siena. Here you can visit the Collegiate church of San Quirico, the Horti Leonini gardens and the church of Santa Maria Assunta along the Via Francigena. There are many places that are worth a visit in the surrounding area as well, such as the green countryside and the Chapel of Madonna di Vitaleta.


9. Pienza

Pienza is a small town situated in the Val d’Orcia, about 50 kilometres away from Siena. Pienza was rebuilt according to humanist urban reorganization and was viewed as an example for many other Italian and European cities. Piazza Pio II, taking its name from the Pope who was born here, is the hub of Pienza since all of the town’s main monuments are located in this square: the cathedral tower, the Palazzo Piccolomini, and the Palazzo Borgia. In addition, the town was named an UNESCO World Heritage Site in 1996. Another local quirk is the love-themed street names: you’ll find a Via dell’Amore (love street) and Via del Bacio (kiss street), for example.



Another place connected to the Via Francigena; another place full of history. This is Radicofani, a stronghold filled with plant life at 900m above sea level, well-known for its fortress overlooking the village. The most important monument in the village is the 13th century Roman church of San Pietro. You should also visit the church of Sant’Agata, the village’s guardian, and Palazzo Pretorio, a large building with a façade lined with the coats of arms of important historical families of the region.