Montefioralle is a village in Tuscany, a frazione of the comune of Greve in Chianti. Town and village were an important stronghold during the wars between Florence and Siena. In 1250 it became the headquarters of the League of the Greve Valley. The town was once endowed with two sets of walls. It had an octagonal shape with four gates. With the fall of the Sienese Republic, Montefioralle lost its prior importance and most of its inhabitants moved to Greve in Chianti.
A house in the circular main street of Montefioralle is pointed out as the birthplace of Amerigo Vespucci. The doorway is identified by the wasp (“vespa”) and V of the Vespucci family.
Montefioralle is an ideal location from which to enjoy real Chianti country life. The village itself is virtually free of cars making it a wonderful place for children to run free. The ancient passageways, formerly the entrances to the castle, fascinate children and adults coming from abroad. Vineyards stretch away in every direction round about and, for those who like a country hike, there are paths and dirt roads (the famous “strade bianche” of Tuscany) passing by renaissance villas, stone farmhouses and ancient parish churches.