The very first thing you should visit in Casole d’Elsa are its oval shaped city walls that include two 15th century round towers and the Rocca, a 14th century fortress that has now become the Town Hall. Hiding in this historic and impressive structure is its contemporary soul, consisting of the Arte Viva gallery. The gallery, which was heavily pushed for by the artist Giuseppe Ciani, is home to a magnificent collection of drawings and paintings by children from all over the province.
Among the historic centre’s prestigious buildings, the Collegiata di Santa Maria Assunta is definitely a stand-out, built in the 12th century in a Gothic Romanesque style. Inside are numerous works of art such as the Cenotaph by Beltramo Aringhieri.
Next to the Collegiata is the Rectory, now home to the Collegiate Archeological Museum where you can discover the town and the history of the surrounding area through various archeological relics from the Etruscan era, paintings and sculptures by the Sienese workshop from the 14th to the 16th century.
Just outside the town centre is the notable Church of San Niccolò, appearing in documents from 1348 onwards. Inside are frescoes by Vincenzo and Francesco Rustici and a Madonna on the main altar from the 14th century Sienese school.