Siena’s Via Cassia The classic crossing of the historic Via Cassia From Siena to Radicofani: 72 KM.

This is an historic road by definition which ties the city of the Palio (Siena) with grande Rome. The great sculptor, time, has left its mark along this ancient consular road. Across the centuries this Roman road has assisted all the changes that have touched Tuscany and its people.

This road can be traveled quickly but it invites you to drive in with a relaxed frame of mind, fully enjoying the ever changing landscape.


From Siena you will leave, heading south following directions for S.S. 2 “Cassia”. Almost immediately the road will be out in the country, into the sunny, open Val d’Arbia, traversing places of historic importance.

For much of the route you will be re-tracing the historic “Via Francigena”, the path that religious pilgrims took from Canterbury to Rome, step after step.

The first stops along the way are the towns of Monteroni and Lucignano. Afterwards you’ll come to the walled town of Buonconvento, you’re entering one of the historically great grain growing centers of Italy.

The landscape and architecture as well as the inhabitants tell a tale of rural culture still more or less intact. One of the more important relics of this peasant past are to be found in the form of “grance”, large warehouses of grain and food stuff, which, among other uses, were historically intended for the poor, pilgrims and the needy and sick. In medieval times the “grance” were buildings which were part of church complexes and abbacies with the function of storing agricultural products. One of the characteristic elements of the Sienese grance is that of their large, defensive nature. Along the route, just before entering the town of Monteroni d’Arbia, you’ll see one of the more important grance, one which is called “Cuna”.

Crossing mainly flat lands, the Cassia arrives in Buonconvento after 27 KM. This is historically a place of encounters and also of battles and trade. The city is laid out in a rectangular fashion and in its original state was surrounded by a defensive wall. It conserves monumental buildings that bear testament to the importance of Buonconvento. The Palazzo Comunale (town hall) has 25 coats of arms which testify to the same number of governing podesta’, from 1270 AD onward. The Museum of Sacred Art deserves a visit, in a wonderful Liberty setting art works from churches and pieve from all around the Crete are gathered for viewing.

Once past Buonconvento the Cassia takes on a more curvy nature. Shortly after the town ofTorrenieri the unmistakable landscape of the Val d’Orcia begins, near the town of San Quirico. You eyes won’t be able to miss the characteristic sign of groups of Cypress tress emerging from the undulating hills.

Here is where the more spectacular stretch of the Cassia begins, passing between the centers of Montalcino on one side and Pienza on the other, it takes you to the magical “borgo” of Bagno Vignoni. Here you will see the magnificent main piazza of thermal water. In fact, there is a common thread that connects this part of the route and it is water. From the park of the Mulini of San Quirico and the thermal waters of Bagno Vignoni, you proceed to the slopes ofMonte Amiata (an extinct volcano) until reaching Bagni San Filippo, another thermal borgo where the water bubbles forth from the ground at 50 degrees centigrade. It’s here that you’ll leave the Cassia, turning left towards the spectacular castle of Radicofani. From the heights of the castle tower you will be able to enjoy an unequaled panorama of the entire Val d’Orcia. The castle of Radicofani played an important strategic role along the Francigena route. It’s notorious history is tied to that of the Ghibellin rebel Ghino di Tacco (mentioned by Dante in the VI stanza of the Purgatorio and by Boccaccio in the Decamerone) who, expelled from Siena, took up residence here in Radicofani and used the castle as a base for his raiding parties.

One final deviation worthy of a visit is that which will take you to the thermal waters of San Casciano dei Bagni. A place for relaxing in the hot vapors of the waters from the slopes ofMonte Cetona, immersed in an environment rich in history and nature.

Where to stay in Siena

There are numerous high quality hotels, villas, apartments and agriturismi (Farm stays) available in Siena, check them out and make a reservation here.