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.
Throughout the 8-km descent to San Gimignano, you can enjoy views of rolling hills, vineyards and olive groves (this is the Vernaccia di San Gimignano territory), country homes and rows of cypress trees. This is a land where human activity and nature exist in perfect harmony.
Before you know it, San Gimignano will welcome you with its 16 towers and city walls. It’s worth taking a short break here to visit the characteristic village, which still maintains its medieval charm, with its narrow streets, historic workshops and 16 towers, all that remain of the 72 that originally stood in the city: the oldest, Torre Rognosa, is 51 metres tall, while the tallest, Torre Grossa, stands at 54 metres and is the only one that the public is allowed to climb.
A few hundred metres before reaching San Gimignano, take the road to the left and follow the directions to Ulignano e Cusona. The road descends for about 3 km. When you come to a curve to the right, take the road on the left in the direction of San Benedetto. The road becomes narrower but it’s still a pleasant ride because it’s a provincial road and there is less traffic. After about 3.8 km, you’ll come to another fork in the road. Take the one to the left and follow the directions for San Benedetto. After a few hundred metres, pass through the town, recognizable thanks to some houses and a small church, and continue down the road to the right, which leads to Certaldo.
At the end of the descent, there is a flat stretch of road that leads to a fork: here, you will need to decide whether to go to the right to make a pit stop at the medieval town of Certaldo or turn left to return to Montaione, passing by Gambassi Terme.
For those who chose the second option, the road will begin to climb upward. The 9-km ascent up to Gambassi Terme might seem endless: the first stretch, up until Badia a Cerreto, is fairly steep, and the road will become easier before it worsens again close to Gambassi Terme. To get through it, you’ll want to find an adequate rhythm immediately in order to save your energy.
Leaving Gambassi Terme behind you, continue to climb for another 2 km until Poggio all'Aglione, where you’ll take the road to the right that leads quickly back to Montaione.
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