The town of Santa Fiora was one of the most important areas in the Middle Ages, mainly because of its role as an operations base owned by of the powerful Counts Aldobrandeschi. Today, the church of Sant'Agostino and Piazza Garibaldi, with its Museum of Caves and Miners, can be visited inside this town, that is in the province of Grosseto.

The first documents on Santa Fiora date to 890 and they provide information about the authority exercised by the monks of San Salvatore on its territory. The rule of the Abbey had already disappeared in 1082, when the Aldobrandeschi, a powerful dynasty of feudatories of Lombard origins, got possession of the territory and built one of their strongholds here.
Therefore, the castle played such an important role that, by XIII century, the Aldobrandeschi were already known as the Santa Fiora and were mentioned in the VI canto of the Purgatory in the famous Dante's Divine Comedy. This illustrious poet talks about the decadence of the family, whose properties were in the hands of the Republic of Siena.
The town was also affected by this fact and its decline started. The marriage between Cecilia Aldobrandeschi and Bosio degli Sforza, from Milan, turned Santa Fiora around in 1439. This event marked both the total decadence of the Aldobrandeschi and the arrival of this important family in the territory of the Amiata. Yet, the Sforza, who had begun to establish their presence also in Rome, soon abandoned this area and gave it to some administrators coming from the Italian capital.
Meanwhile, Santa Fiora entered the Tuscan Grand Duchy at the half of the XVI century. The situation of this town, which had already been debilitated by a new feudalization under the Medici in the XVII century, was further worsened by the "illuminated" reforms of Pietro Leopoldo of Lorraine. The end of feudalism caused the disappearance of important seigniories in this area that had been the only ones to invest in agriculture until that moment, even though the population, who had been oppressed by the abolition of the civic use of pastures and lands, did not benefit from these investments.
When the community of Santa Fiora (set near the borders with the then existing State of the Church) and its population entered the Kingdom of Italy their conditions were pitiful. Fortunately, this town succeeded into recovering its economy, to the extent that two of its hamlets, Castell'Azzarra and Semproniano, became independent with their own administrations in the 60's.