The main draw in Montaione is San Vivaldo, a remarkable Renaissance sacred complex of eighteen chapels reproducing Jerusalem's holy sites in miniature — one of the most significant pilgrimage sites in Tuscany, yet almost unknown outside the region. In town, the Palazzo Pretorio Civic Museum holds Roman and Etruscan finds from excavations nearby, and the Roman cistern behind the village is a beautifully preserved ancient water reservoir.
The hamlet of Castelfalfi nearby has a medieval castle and a golf course set among Tuscan hills. The surrounding countryside is excellent walking and cycling territory, particularly on quiet gravel roads through vineyards and olive groves. The hills around Montaione form part of the Via Francigena pilgrim route corridor, with day walks possible along historic ridge paths linking to nearby Gambassi Terme.