Etruscan and Roman in origin, Gaiole in Chianti became an importal trade center during the Middle Age and the Fridolfis erected fortifications and castles. Brolio castle, always belonged to the Ricasolis, was equipped with bastions and lookout towers, during the Medicis domination and, after the conquest by Siena, was converted into the Ricasolis' private residence.
Abbey Coltibuono, a monastery existing since 1051 and owned by the vallombrosiani monks until 1810, was transformed into a villa too.
The parish church of Santa Maria a Spaltenna, in Romanesque style, and some elements of the façade and the apsis of the church of San Giusto in Salcio (the other parts have beeen completely rebuilt) are very ancient.