The town of Barberino Val d'Elsa is a beautiful medieval village surrounded by the green Tuscan countryside between Florence and Siena. Situated along the ancient Cassia road which connects Florence to Rome, it offers a stunning panorama of the Chianti region.
Even though there are no particular museums or monuments to visit, I recommend you stop and walk along the three streets in the center to enjoy the quiet and peaceful tranquility of the town, breathing in a little of its glorious history.
The history of Barberino is closely tied to Semifonte, a nearby town that was completely destroyed by the Florentines in 1202. Legend has it that the stones used to fortify the city, which became a Florentine outpost, came from the destroyed remains of Semifonte. Barberino maintains its original medieval look with an elliptical plan crossed by two longitudinal streets which are its beauty and the reason to stop here, even if just briefly.
From the well conserved Sienese Gate to the south you enter the main street, via Francesco da Barberino, where there are several beautiful buildings with ancient doors and swallow nests on their upper gutters. Halfway down the street, the Palazzo del Podestà faces the small square with its facade decorated with the coats of arms of important noble families, including Florentine families.
At the end of the street is the Florentine Gate, although no longer the original one which was destroyed at one point, and next to it is the old pilgrim hospital, founded in 1363 and now housing the modern town library. Along this other parallel street you'll find an old bakery, one that has been producing traditional Tuscan bread and schiacciata for three generations. I highly recommend a stop and buying a piece of the delicious schiacciata!
Then you reach the magnificent Church of St. Bartholomew, rebuilt in the neo-gothic style in 1910. Inside is a fragment of a 14th century fresco and a panel painting by the Master from Barberino from the 16th century depicting the Virgin Mary with child giving a rosary to St. Catherine from Siena and St. Dominic.
Once you visit Barberino, I strongly suggest you take some time to visit the stunning parish church of Sant'Appiano and the Chapel of St. Michael in Semifonte, both located in the surroundings. The history of Semifonte is interesting, since in the Middle Ages it was a large, important city for the age and thus considered a great enemy by Florence. At one point, its great influence in the Val D'Elsa led to the decision by Florence to attack it. It took four years of siege, and in 1202, Semifonte was conquered and completely destroyed by the Florentines. To prevent its reconstruction, Florence prohibited anyone from building on the site, an edict that has been respected except for the construction of the Chapel of St. Michael in the 16th century in memory of the people of Semifonte. Visiting it today and thinking of the site makes for an interesting stop along your Chianti itinerary.