Castelfiorentino is a country town plunged into Chianti green hills.
Our territory goes proud of its numerous significant masterpieces, such as the frescoes attributed to Benozzo Gozzoli, the Church of S. Verdiana, Oliveto Castle, but not of less value are the many aristocratic villas built in the area of Meleto, Granaiolo, Cambiano, Cabbiavoli and Montorsoli noted for their historical and architectural prominence.
Collegia church of Sts. Lawrence and Leonard (13th-14th centuries). It houses a crucifix by Giovanni Pisano (14th century).
Romanesque-Gothic church of St. Francis (13th century), with a Madonna with Child by Taddeo Gaddi, and other works by Cenni di Francesco, Giovanni del Biondo and other 15th century Florentine schools paintings.
Pieve (pleban church) of Santi Ippolito e Biagio, with a 14th-century crucifix and two 15th-century frescoes
Oratory of Santi Lorenzo e Barbara.
Sanctuary of Santa Verdiana (18th century)
Romanesque pieve of Santi Pietro e Paolo, at Coiano (11th century)
According to a popular legend, Membrino was the name of a boy, who, in XVI century, saved the town from the enemies' attack, warning the inhabitants.
Population, to express its gratitude, put a simbolic portrait on the bell of the clock town , in order to remember him. Nowadays the bell tower is called: "Membrino".
The Francigena trail is a medieval route that linked Canterbury to Rome.
Castelfiorentino was crossed by the Francigena Trail. The path ran along the current town of Gambassi Terme, Castelfiorentino, Certaldo, Poggibonsi and San Gimignano; from here pilgrims continued towards Siena and Rome.
Castelfiorentino has a new museum in a building designed specifically for the frescoes of one of the most important painters of the Renaissance. The Museo Benozzo Gozzoli was conceived and constructed for the purpose of giving a home to the frescoes which Benozzo painted for two chapels built near the city. The frescoes, which have been completely restored, are those of the Tabernacolo della Madonna della Tosse (Chapel of Our Lady of the Cough) and those of the Visitation.