Montefioralle, a medieval gem in the heart of Chianti


Last Updated on November 8, 2023 by Laura Teso

Motefioralle is a perfectly preserved medieval hamlet, nestled among the rolling hills of Tuscany, part of Greve in Chianti municipality. 

Listed among the borghi più belli d’Italia, i.e. the most beautiful villages in Italy, is a tiny, tiny village (less than 100 inhabitants) with narrow cobblestone streets, stone houses, and ancient castle walls. Being there feels like a step back in time

Montefioralle Tuscany

A bit of background

Montefioralle dates back to the 11th century. It was built as a fortified settlement, strategically located between Florence and Siena. Therefore it played an important role in the wars between the two cities. The village developed around the castle at the top of the hill. So it is enclosed by elliptical city walls, largely preserved. Of the castle, however, only a rectangular structure remains to this day. You can still see the three access gates to the village and some towers, which over time became private housings.

The name was originally different: Monteficalle. A word made of Monte, mount, and ficalle, from fico, meaning fig, because of the fig plants that covered the slopes of the hill around the castle. It was later modified in Montefioralle to sound more elegant.

Montefioralle Italy

Things to do in Montefioralle

  • Visit the church of Santo Stefano, which dates back to the 12th century (but renowned in 1600 and 1800). If you find it open. When I was there, it was not, sadly. 
  • Take a walk through the village’s narrow streets and alleyways, and admire the stone houses and medieval architecture. One of the houses was particularly beautiful. Thanks to the owners who adorned the whole doorway (and more) with plants and flowers. It was so beautiful I couldn’t stop taking pictures. Photo below.
  • Among the palaces, locals say there’s also the house of explorer and navigator Amerigo Vespucci, the one who gave the name to America. On the architrave of the house you can see the coat of arms and the “V” of the Vespucci family.
  • The village is also famous for its vineyards which produce quality wines, including the famous Chianti Classico.
  • Sadly I did not stop there to eat there and later I regretted that. In fact I heard a lot of good things about the restaurants there (Il Guerrino e L’Desio). They both have lovely views over the hills surrounding the village. Well, next time. 
  • Wine lovers can take part in a wine tasting in the wineries of the surrounding. There’s also a wine shop right in the center of the village.
  • Not far from Montefioralle, visit the suggestive Pieve di San Cresci. It is one of the most important Roman structures in the Chianti region. Think that the first documented about this church dates back to the year 963 (but there were several restoration works over the centuries). 
Montefioralle Chianti

Is it possible to reach Montefioralle by train or bus?

Sadly not! The railway doesn’t reach it. Regular buses only reach Greve in Chianti. So it is better to have a car.


Sagra delle Frittelle (Frittelle Festival): On March 19, Saint Joseph’s Day (Father’s Day in Italy). Classic Italian frittelle are sweet fried dough balls, usually filled with raisins or custard. In Montefioralle by frittella they mean fried sweet balls but the main ingredient here is rice cooked in milk. It’s a tradition dating back to the Renaissance. Since then, the families of the town have the custom of preparing these treats in honor of Saint Joseph. 

Montefioralle Divino, a Wine Festival taking place every year on the fourth weekend of September. Organized by local winemakers, it is an opportunity to taste local wines. Attention: since it is difficult to park outside the hamlet during the festival, you can take advantage of a free shuttle service. It departs from Piazza Trento in Greve in Chianti.

Is Montefioralle worth a visit? 

Montefioralle is a village that offers an authentic experience of medieval Tuscany, with its cobbled streets, its ancient walls and its rich food and wine tradition. It is an ideal place for those seeking tranquility, beauty and a connection with Italian history. If you are planning a visit to the Chianti area of Tuscany, Montefioralle definitely deserves a place on your list of must-see destinations. The visit requires little time but you can combine it with other lovely villages in the area, such as Greve in Chianti or Barberino Val d’Elsa.

You can find other Tuscany destinations here: Then you can take a look at my Instagram account!


Map of the village

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