You leave from Piazza Gramsci in Montaione turn immediately left onto Viale Filicaja. After a short descent, follow the signs for San Gimignano, a stretch of about 3 km uphill passing in front of a Roman Cistern of the II century AD, and then reach Poggio all’Aglione from where you start to go down for about 500 meters until you reach a junction.
Turn right and after a short descent, the road begins to go up. Keep riding until you reach Castagno d’Elsa. After passing the village of Castagno d’Elsa continue for about 600 meters until you come to a junction near a sharp bend to the left. Start to turn on a straight line leaving the main road and continue to pedal for about 2.2 km until, in Camporbiano, turn left towards San Gimignano.
In the 8 km, mostly downhill, that from here are left to San Gimignano, you will steep in a landscape made up of rolling hills, fields planted with olive groves and vineyards (you are entering into the realm of Vernaccia di San Gimignano), country houses and rows of cypress trees. A territory where the activities and nature come together in perfect balance.
In less than no time you will find in front of you the spectacle of the town of SanGimignano with its 11 towers and city walls, which, resting on a high hill, will welcome you.
At this point, it is worth making a short refreshing stop to visit the village of San Gimignano, which still maintains all its medieval charm with its narrow streets, old shops and especially with its 16 towers of the 72 original: the oldest one, the “Tower Rognosa” is 51 meters high, while the highest, the “Torre Grossa”, the only one on in which access is allowed to the public, is 54 meters.
If you choose not to stop and visit San Gimignano with more time, a few hundred meters before the village of San Gimignano, take the road on the left following the signs forUlignano and Cusona. The road goes down for about 3 km until close to a curve on the right you have to take the road to the left in the direction of San Benedetto. The road becomes narrower, but it is a pleasure to follow it because, as a side street, you will find very few cars. After about 3.8 km you will come to another junction. Turn left following the signs forSan Benedetto. After a few hundred meters go past the village of San Benedetto, recognizable by a few houses and a small church that you will see on your right as you go down in the direction of Certaldo.
At the end of the descent, travel a stretch of flat road until you reach a junction, where you can choose to turn right and make a short visit to the medieval village of Certaldo, or turn left to return to Montaione through Gambassi Terme.
For those who have chosen the second option, the road begins to go up. 9 km of ascent to get to Gambassi Terme might seem endless considered that the first part of the ascent up to Badia a Cerreto is quite steep and then becomes easier to pedal and tightens again when you approach Gambassi Terme. You should then immediately look for the right gear and pedaling rhythm and think about saving your energy.
After leaving the town of Gambassi Terme continue to go up for about 2 km until Poggio all’Aglione and then take the right path that will take you quickly to Montaione.