The Via Cassia is a historic road par excellence, and it connects Siena with Rome. History walks this ancient consular route, which has remained a constant throughout the centuries, running through the Tuscany that everyone seeks and dreams of. You can devour the miles on the Via Cassia, but it also encourages a more relaxed ride, allowing your eyes to follow the curvature of the landscape as it passes by.
We start in Siena and head south, following the signposts in the S.S.2 "Cassia". The road dives into the Val d'Arbia and passes sites of great historical significance, while largely tracing the course of the Via Francigena, where the sense of adventure is imbued with the spirit of the pilgrims who walked from Canterbury to Rome.
The next stops en route are the towns of Monteroni and Lucignano, which invite you to pause on the way to Buonconvento. We are passing through Italy's historic bread basket: certainly, the land is littered with grance, great grain silos and food warehouses which, apart from anything else, served as rest stations for the poor, for pilgrims and for the sick. A defining feature of the Sienese landscape, the grance also came in useful as bulky defensive structures. A few miles before the village of Monteroni d'Arbia, you come to one of the most important grance of them all, that of Cuna.
After 27 km you reach Buonconvento, traditionally a meeting place, a market place and even a battleground. Its rectangular plan has been bordered by the city walls since time immemorial, and within them you find some monumental buildings, stocked with memories of time past. Apart from the Town Hall, which is decorated with the coat-of-arms of no fewer than 25 of the podestà who governed the town until 1270, you should take time to visit the Val d'Arbia Sacred Art Museum, a magnificent example of the Liberty style, whose walls contain artworks from the churches across the Crete Senesi. You leave Buonconvento and, not far after Torrenieri, the Via Cassia rises over the unmistakable landscape of the Val d'Orcia, with San Quirico nearby. You will not have any difficulty noting the cypress trees that spike from the undulating hills, one of Tuscany's most famous features.
The most spectacular stretch of the Cassia starts here. On the way from Montalcino to Pienza you arrive at the town of Bagno Vignoni, where you will see the magnificent main piazza, which is swimming in thermal water. In fact, there is a common thread that connects this water with this part of the route. From the park of the mills around San Quirico and the thermal waters of Bagno Vignoni, you head to the slopes ofMonte Amiata (an extinct volcano) and eventually reach Bagni San Filippo, another spa town where the water gushes from the ground at some 50 degrees centigrade.
Here you leave the Cassia and turn left towards the spectacular castle of Radicofani, whose tower offers an unparalleled view of the entire Val d’Orcia. The castle played an important strategic role along the Via Francigena. Its dubious fame is tied to that of the Ghibelline rebel Ghino di Tacco, a man notorious enough to be mentioned in the sixth canto of Dante's Purgatorio and also in Boccaccio's Decameron. Expelled from Siena, he took up residence here in Radicofani and used the castle as a base for his raiding parties.
It's worth one final deviation to visit the thermal waters of San Casciano dei Bagni, the perfect place for steaming in soothing vapours on the slopes of Monte Cetona, surrounded by a land rich in history and nature.
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