Montaione is a small medieval hill town in the Valdelsa, halfway between Florence and Volterra. It sees far fewer visitors than its neighbours, which is part of the appeal — this is workaday Tuscany, not postcard Tuscany, though the views from the old centre are postcard-worthy all the same.
The town preserves a compact medieval layout and a pleasant piazza. On the road to Gambassi Terme, about a kilometre out, stands the Villa Da Filicaia, built on the site of a Roman settlement and once gifted by the Medici to the poet Vincenzo da Filicaia. A Roman cistern nearby hints at the area's ancient history. The Palazzo Pretorio Civic Museum in the old centre holds local archaeological finds. Four kilometres south-west, the sacred complex of San Vivaldo — eighteen Renaissance chapels reproducing Jerusalem's holy sites in a wooded hillside — is one of the most remarkable and least-visited sights in all of Tuscany. The medieval hamlet of Castelfalfi, with its castle and golf course, lies six kilometres to the west. Montaione makes a quiet, affordable base for exploring the Tuscan countryside by car.