Starting in piazza Gramsci in Montaione, turn immediately to the left down viale da Filicaja. After a brief descent, following the directions for San Gimignano, you’ll begin a climb upward for about 3 km, passing by the 2nd-century CE Roman Cistern before reaching the village of Poggio all'Aglione; from here, the road will start descending for about 500 metres until you come to a fork in the road.
Turn to the right and, after a brief descent, the road will begin to climb upward. Continue until Castagno d'Elsa. Passing by the town, continue for about 600 metres before arriving at a fork close to a sharp turn on your left. Go straight, leaving the main road behind you, and continue pedalling for about 2.2 km until, in the town of Camporbiano, you turn left following the directions for San Gimignano.