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Monteriggioni as seen from the Via Francigena
Photo ©Kinzica Sorrenti

10 small towns near Siena

Explore our selection of small towns in the surroundings of Siena

Our post about 10 small towns near Florence was so popular that we decided to share more ideas about another beloved area of Tuscany: in this article we’ll explore 10 small towns in the surroundings of Siena. Some of them are off the beaten path, while others are more famous.


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. Read more here.

Montepulciano - Credit: Xavier on Flickr

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. Read more here.

Aerial view of Monteriggioni
Aerial view of Monteriggioni
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. Read more here.

San Gimignano skyline from La Rocca
San Gimignano skyline from La Rocca - Credit: Stefano Cannas - Visit Tuscany Social media team
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”. Read more here.

Torrita di Siena street view
Torrita di Siena street view - Credit: Liu Joey on Flickr

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! Read more here.

Sunset in Montalcino
Sunset in Montalcino - Credit: Diego Solari on Instagram

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). Read more here.

Buonconvento Palazzo Pretorio
Buonconvento's Pretorio Palace - Credit: David Bramhall on Flickr
Castellina in Chianti

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.

Countryside around Castellina in Chianti
Countryside around Castellina in Chianti - Credit: Fernando López on Flickr
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. Read more here.

Collegiate church of San Quirico
Collegiate church of San Quirico - Credit: Gabriele Cantini

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. Read more here.

Pienza - Credit: Serena Puosi

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. Read more here.

Radicofani view
Radicofani - Credit: Simonetta Viterbi on Flickr

The original version of this article was written by Serena Puosi.

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