Castellina in Chianti was born as a military outpost, repeatedly contested between Siena and Florence. The ancient medieval fortress and an impressive hexagonal wall still visible today are evidence of the struggle between the two cities. The wall was destroyed and rebuilt many times and legend has it that even Brunelleschi was asked to work on the project of building new walls for the town.
Today Castellina is an important centre on the Chiantigiana road with large forests and rich fauna all around.
Here you can visit the neo-Romanesque church of San Salvatore just outside the town and Montecalvario, a burial complex consisting of four ancient Etruscan underground tombs. Outside the city centre, there is also the Fortress with its tall tower to be visited: it offers, in fact, a stunning panorama of the town and countryside. The Fortress is also the Town Hall and houses the Archeological Museum of Chianti.
The most characteristic street of Castellina is the medieval Via delle Volte, once an impressive underground tunnel used by the guards, now a covered street with shops and restaurants.
Castellina is also the place where in 1924 the Chianti Classico Consortium was born, and since 1984 it has the DOCG mark. Read more about Castellina here.
From Castellina you can go down to the Elsa Valley and back to San Gimignano and Monteriggioni or, alternatively, in a short time you’ll reach Siena through Fonterutoli. Let's take a detour from the SR 222 and head to Radda in Chianti.