The village of Montefioralle is one of the most well-preserved medieval villages in all of Tuscany. Originally a walled castle, it is located in the heart of the Chianti Classico region on a low ridge above the town of Greve.
Castello di Montefioralle, first mentioned in 1085, was built with two parallel octagonal walls. The stone walls still exist, but the outer defensive wall evolved through the ages as houses were built against it, using the existing structure. Now a ring of homes and a narrow circular cobblestone street fills the space between the original walls. The four original gates still exist, but without the two descending doors at each guarded post that once provided security.
During the Middle Ages, Montefioralle, then known as Monteficalle (so honored in an epic poem by Boccaccio in 1344), was one of the largest military and administrative settlements of the area. It belonged to well-to-do Florentine families – Ricasoli, Benci, Gherardini and Vespucci. Amerigo Vespucci, the Tuscan adventurer and mapmaker, who “discovered” the harbor of New York and gave his name to America, lived here in the late 1400s.
In 1325, the castle was sacked by Castruccio Castracani, the Duke of Lucca. (An interesting tale of the life of Castracani was written by Machiavelli over 150 years after the Duke’s death from a malady feared most by Italians: raffreddore – a chill caught from the dreaded draft in 1328 after his greatest victory over the Florentines).
At the highest point of the village, in one corner of the inside wall, stands the church of S. Stefano, rebuilt in the 17th century and then again in the18th century. A large manor house across from the church was once the original castle keep.
In the 18th century, when Montefioralle was not necessary for its original defensive purpose, the village lost its predominance to the local market town of Greve.
Today, Montefioralle is know for its Kodak moments, its sagras (festivals) (the Sagra delle Frittelle (small fried balls of rice with a variety of other ingredients) in mid-March, among others), and as a location for picturesque weddings. There is an excellent osteria (Taverna del Guerrino) inside the walls, a wine tasting room for local vintages, but not much else.