Among the major monuments worth visiting are the Museum of Sacred Art and and the Church of Mercy (or Santa Maria al Prato), which has a rich collection of art, including a Crucifix by Simone Martini.
The city is separated in two parts by Via Cassia. It is located some 15 km from Florence, and 45 km from Siena, bordering on the municipalities of Greve in Chinati and Tavernelle Val di Pesa.
It is located in a subzone of the Chianti Classico area, thus it is famous for its wine and extra virgin olive oil, and its agricultural products in general.
The territory of San Casciano was already inhabited in Etruscan times, as demonstrated by archeological finds, like the Montefiridolfi (the Arciere tombs) and Valigondoli (the digs of Poggio La Croce). A plaque with the writing “Decimo” can still be read at the Pieve di San Cecilia, near San Casciano, affirming that this was an important thoroughfare that connected the Florence and Siena colonies. Archeological finds and layered toponomastics attest to the city center’s ancient origins.
Indeed, there are four parishes (Decimo, San Pancrazio, Sugana and Campoli) that are located very close to one another, alongside a large amount of churches that were likely at the service of the various ‘peoples’ in the area. This dense group of places of worship were likely already there in the Middle Ages. These churches were flanked by castles and feudal residences belonging to powerful Florentine families, like the Buondelmonti and the Cavalcanti families. Today, these homes and castles have been transformed into the villas and farm homes, like Bibbione, Castelvecchio, Fabbrica, Lilliano, Montefiridolfi, Montepaldi, Pergolato and others), and are now considered humble country or rural homes (Argiano, Castelbonsi, Montauto, Monteclavi, Montecampolesi, Montefolchi).
San Casciano was a feudal city run by the bishops in Florence, who, in 1241, conceded the first civil statues. In 1278, the town came under the rule of the Florence Republic. Shortly thereafter, it became the home of a League and Podesteria that included the Lega di Campoli, for a total of 40 ‘peoples’. San Casciano was purposefully located along an important transportation route, the Via Cassia, which connected Florence to Siena. Another important factor in the development of San Casciano was the growth in agricultural production thanks to the increase in sharecropping that facilitated the spread of trading posts in nearby cities, like Mercatale and the castle of San Casciano ‘a Decimo’.
In the early 1300s, in fact, with no defense walls or fortresses, San Casciano was often targeted by mercenary groups. It was occupied first by Emperor Arrigo VII from November 1312 to January 1313, then by Castruccio Castracani, who sacked it in February 1326, and finally by Fra’ Moriale in 1343. Following these events, the Florence Republic decided to fortify the city in 1354. The fortified walls that were a slightly polygonal in shape were completed in 1355, and in 1356, a quarterdeck (which partially exists today) was added to increase the city’s defenses.
Previous to this, the Duke of Athens had planned to transform the village into a castle and rename it “Castle Ducale” but this idea soon disappeared, just like the Duke. In 1420, San Casciano welcomed Pope Martino V. In 1494, Charles of France set up camp near the village, but he never visited it. Before he left the area, however, he gave a significant donation to the local Franciscan convent. In 1512, near L'Albergaccio (in Sant'Andrea in Percussina) Niccolo’ Machiavelli began his exile, and it was in that same period that he wrote some of his most renowned works, like the Prince and the Mandragola. With the birth of the Grand Duchy, San Casciano ceased being a military stronghold and its history followed that of the region.
In 1880, after the Tuscan Grand Duchy was replaced by a unified Italy, the voters of San Casciano elected Sidney Sonnino as a municipal deputy. Sonnino would go on to become prime minister from February 8 to May 29, 1906, and from December 11, 1909 to March 31, 1910. Some years earlier, in 1891, San Casciano was connected to Florence by way of a steam train line that was aimed at linking Florence with the Chianti area, which was previously left out of the regional train line.
On July 26, 1944, San Casciano was heavily bombarded by the Allied forces, and together with the land mines left by the Nazis, the town was almost reduced to a rubble. The city’s reconstruction was slow.
The San Casciano countryside is full of villas, including Villa I Collazzi and the Tattoli Villa near Cerbaia and S. Andrea in Percussina,Villa Bossi-Pucci, known for Albergaccio, the famous residence of Niccolò Machiavelli.
San Casciano is also not far from Impruneta, an area known for its brickwork. Here, visitors will find old kilns and workshops that are still produce terracotta.
In the picturesque landscape of the Florence Chianti you can discover the most untouched parts of the Tuscan countryside by travelling along the Chianti Colli Fiorentini Wine Trail.