Leaving Porta Pispini, to the left, take the road downhill to Porta Ovile, to continue towards the railway station and take the cycle path that runs parallel to Viale Giovanni Paolo II, also known as Strada Fiume, and which takes us to the SR 222 Chiantigiana.
After just one kilometer, in Colombaio we take SP 102 of Vagliagli on the right. At the beginning the road slides downhill until you reach the valley floor. Arrived at the end of the descent, we have seven kilometers of uphill stretches ahead, some of them even challenging, which take us up to Vagliagli, in the heart of the Chianti. If you prefere to soften the path without reaching the town, after a couple of kilometers you can take the road on the right for Pontignano.
Otherwise we continue to Vagliagli from which you can admire an extraordinary view over the hills of this renowned “land of wine”, known throughout the world.
From Vagliagli we go back, slightly downhill for almost five kilometers to the crossroads that on the left indicates Pontignano and its splendid Certosa.
After Pontignano, the road begins to descend gently, then with slopes well over 10%. We thus arrive in Ponte a Bozzone where we follow the signs for Siena; we go uphill again for about a kilometer and then we take the road that leads to the village called Monteliscai.
The road we take towards San Giorgio a Lapi is now almost free of traffic in an alternation of short climbs and flat stretches; near the church of San Giorgio a Lapi, which rises high on a hill overlooking the first Chianti spurs, begins a stretch of dirt road, the penultimate that professional cyclists travel, in the opposite direction, in the now famous race world tour “Strade Bianche” which starts and ends in Siena. The dirt descent of Colle Pinzuto is quite difficult and challenging.
Once at the bottom of the valley marked by the Bozzone torrent, again on the asphalt, we take the right, uphill, and then descend to the first outskirts of Siena. Porta Pispini is just over a kilometer away.