The Via Francigena, one of the great historic pilgrimage routes of medieval Europe, passes through the Valdelsa between Florence and Siena — and the hills around Montaione lie directly on its path. The modern waymarked trail follows the ridge roads and gravel tracks (strade bianche) that medieval pilgrims would have used, giving walkers a journey through classic Tuscan countryside: vineyards, olive groves, cypress avenues, and quiet hill towns.
Montaione is not directly on the main Francigena route — the waymarked path passes slightly east near Gambassi Terme — but the local trail network connects to it easily. Day walks from Montaione along Francigena sections can be done without transport back, using taxi services from Gambassi Terme. The terrain is gentle and the paths are well-maintained. Pilgrim credentials (passports stamped at churches along the route) can be obtained at local churches; Montaione's parish church is one of the stamping points.