Guide to visiting Montefioralle
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The castle of Montefioralle in the Chianti Classico

Montefioralle is a small medieval village, nestled among the rolling hills and postcard views of Chianti. Rightly considered one of the “Most Beautiful Villages in Italy, Montefioralle is a perfect example of a Tuscan hilltop village. If you want to visit one of those picturesque villages that animate the Tuscan countryside, Montefioralle is certainly an excellent choice.

Part of the municipality of Greve in Chianti, Montefioralle is a real gem. Walking through its irregular streets, between stone houses and picturesque views, you can savor a particular atmosphere, remaining suspended in time, light years away from the stress of everyday life.


Born around a feudal castle, Montefioralle is remembered for the first time in 1085 when it was known as castro Monteficalli. The original name, “Monteficalle”, seems to be linked to the presence of fig trees that once grew in the fields around the castle. The current name dates back to much more recent as it dates back to the eighteenth century.

Some documents, dating back to the 12th century, suggest that for a certain period the castle was controlled by families of Lombard origin. These were followed by other important families such as those of the Ricasoli, the Benci, the Gerardini, and the Buondelmonti.

Being along the important Via del Guardingo di Passignano, which once connected Val d’Elsa, Val di Pesa, Val di Greve and Valdarno, the castle of Montefiorelle had a certain strategic and political importance.

Between the fourteenth and fifteenth centuries, Montefioralle was involved in the struggles between Florence and Siena which at that time were competing for the Chianti area. In 1325 it was besieged by Castruccio Castracani and at the end of the fourteenth century it suffered the raids of Alberto da Barbiano.

After a long back and forth, the castle finally passed under the control of Florence, which for a certain period recognized it as a role in governing the surrounding lands. A town hall and the hospital of San Maria del Bigallo were located here. Among the families who lived in the village of Montefioralle, the Vespucci family stands out, including the famous navigator and explorer Amerigo Vespucci.

Montefioralle (Photo by lo.tangelini / CC BY)

What to see in Montefioralle

Montefioralle has gone through many centuries of history managing to maintain a clear urban identity. Compared to other castles in the area such as those of Panzano and Cintoia, Montefioralle has been much better preserved. This is due to the fact that the castle remained somewhat isolated and in its own right when the market from which the center of Greve in Chianti was born developed downstream.

The village developed in concentric rings around the castle which is located in the highest part of the hill. The inhabited center is built on the basis of an elliptical plan, well delimited by the medieval walls. Even today the medieval walls of Montefollonico are preserved quite well and you can also see the remains of some defensive towers.

Montefioralle (Photo by Elisa Rolle / CC BY)

Church of Santo Stefano

The Church of Santo Stefano is located at the highest point of Montefioralle, right in the center of the village. Built in medieval times and originally in Gothic style, the church was rebuilt between the seventeenth and eighteenth centuries and further remodeled a century later.

Inside there are several works of great value. The most important is probably the Madonna and Child by the Master of Montefioralle, but the Annunciation and Saints by the Master of Sant’Ivo, the Trinity and Saints attributed to the Master of the Epiphany of Fiesole and the canvas with the Saints  Michael the archangel, Jacopo, Stefano and Domenico by Orazio Fidani are also not to be overlooked.

Vespucci House

During the walk you will take in Montefioralle, sharpen your eyes to locate the Vespucci house. Above the door of one of the buildings you can see the coat of arms of the family from which the great Florentine navigator Amerigo Vespucci comes, the one who gave the name to the “new world”, America. Easy to recognize, the coat of arms has an oblique band with wasps above.

We can say that this is truly a “Land of saints, poets and navigators”, especially navigators since another giant of sea exploration like Giovanni da Verrazzano also comes from these parts; not far away is the Verrazzano Castle, where the great navigator who first discovered the Bay of New York was born in 1485.

Pieve di San Cresci

Not far from Montefioralle, the delightful Pieve di San Cresci is also absolutely worth a visit. Built in the 12th century, the church has been remodeled several times over the centuries giving life to an interesting mix of Romanesque, Baroque and Neo-Gothic styles.

The exterior is very interesting because it has rather rare elements in the panorama of Tuscan churches. The interior, in Baroque style (a decidedly more sober version than the Baroque we are used to), preserves some frescoes and statues while other works, once kept in the parish church, are now in the Museum of Sacred Art in Greve in Chianti.

Pieve di San Cresci in Chianti
Pieve di San Cresci (Photo by Vignaccia76 / CC BY)

Montefioralle Wine

Montefioralle is located in the Chianti Classico area, so a good glass of wine cannot be missed during your visit. Around Montefioralle there are several wineries and farms where you can have a wine tasting while admiring the beauties of Chianti.

Events and festivals in Montefioralle

In Montefioralle there are a couple of festivals linked to the local food and wine tradition. On the occasion of the feast of St. Joseph (which is March 19), there is the Sagra delle Frittelle. Rice fritters are a product that comes from the peasant tradition of this area. Fried in a pan and then dusted with sugar, the frittelle di San Giuseppe are a real treat that just can’t be resisted!

Since we are in the Chianti Classico, Montefioralle cannot fail to have events dedicated to wine. The first is called I Vini del Castello and takes place in May. The second is the Montefioralle Divino, a wine festival organized and promoted by the Montefioralle Viticulturists Association in September. These are the perfect opportunities to get to know the wines of the area and get in touch with the producers.

In addition to the Castello wines and the Montefioralle Divino, I also point out I Profumi di Lamole which is held in June in Lamole (another fraction of the municipality of Greve in Chianti) and the Chianti Classico Expo in September in Greve in Chianti.

How to get to Montefioralle

Montefioralle is located just over a kilometer away from Greve in Chianti. It is not served by public transport but can be easily reached from Greve either by car or on foot. The walk from Greve to Montefioralle can be a bit tiring because you have to climb a bit, but it only takes 20 or 30 minutes and during the walk you can admire a beautiful panorama made of rolling hills and olive trees.

To get to Greve by car, both those coming from Florence (30′) and those coming from Siena (40′) must take the Strada Chiantigiana (SP222).

Greve in Chianti does not have a train station but can be reached by bus from Florence; near the Santa Maria Novella station, you will have to take the Sita line 365 which takes about an hour.

Where to sleep in Montefioralle

In Chianti there are many farmhouses also with swimming pool where you can stay enjoying all that this land has to offer: hospitality, food, wine, relaxation, views etc.
Alternatively you can evaluate some castle; there are many in the area that have been converted into luxury resorts. In Greve you will also find hotels and holiday homes.

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