Montaione took its name after the Allone di Lucca, and was documented in the Middle Ages as Mons Allonis. In the 1200s Montaione became known for glass working, which spread throughout the Valdelsa. In 1257 the town was struck by the wars between San Gimignano, Volterra and San Miniato, but mostly gravitated around Florence.
Today Montaione is a quiet place with a delightfully maintained town centre featuring three parallel streets that meet where the gate once stood. Sadly very little remains of the old walls, destroyed for the most part (in addition to the gates and the towers) by German bombings in 1944. Decorated with coats of arms on its facade, the fourteenth-century Palazzo Pretorio is a beautiful building: it is home to the library and the Natural History Museum.
The church of San Regolo is worth visiting. Erected in the thirteenth century and rebuilt in 1635, it houses an important Madonna and Child attributed to the Cimabue school.
With its plentiful farmhouse accommodation, Montaione is the perfect destination for country lovers. Over the years country homes and villages, abandoned in the 1960s, have been renovated and converted into charming places to stay.The Montaione area vaunts a network of well-signposted hiking trails. In the countryside around the town, it’s worth checking out the Sacro Monte di San Vivaldo, where the Francescan friar Vivaldo Stricchi da San Gimignano took up a hermit’s lifestyle in the 1300s, found dead in the hollow of a chestnut tree that was his home. After his death an oratory was erected on that spot, which Fra’ Tommaso da Firenze extended in 1515 with a series of chapels decorated in terracotta showing scenes and episodes from the life and passion of Christ and which depict Palestine. Over the years, this mysterious and evocative place acquired the nickname “the Jerusalem of Tuscany”.