By bike from Siena to Chianti

We are only a few kilometers away from Siena in this itinerary – from time to time, we can glimpse its outline around a few bends. To the west the Montagnola Senese and the nearby Chianti chain; to the south the Amiata, the Radicofani knoll and Mount Cetona: along our route, the panorama opens up, allowing us to admire the beauty of the area.

We cross Porta Pispini to leave Siena and, makinga left-hand turn, we head down the road that takes us downhill to Porta Ovile. As we approach the train station, we can take the bike path parallel to Viale Giovanni Paolo II - the Strada Fiume - that will lead us onto Regional Road 222 Chiantigiana.

After about a kilometer we arrive at the locality of Colombaio where, on the right, we take the less busy Provincial Road 102 of Vagliagli. Once the descent is over, a climb begins, which continues in spurts, including some challenging ones. We reach the 505-plus meters above sea level of Vagliagli: we are in the middle of Chianti territory. A detour is possible after a couple of kilometers uphill, on the right, following the signs for Pontignano: this will soften the route a bit. Otherwise, we proceed to the small village of Vagliagli where a magnificent view of the hills of this famous wine land awaits us.

After a well-deserved stop in this characteristic little town, it is time to turn back: now we are on a slight descent for almost five kilometers until we reach the junction that, on the left, indicates Pontignano, memorable for its beautiful Certosa.

The road begins to descend after Pontignano, with peaks even over 10%. Once in Ponte a Bozzone, we follow the signs for Siena. Another kilometer or so uphill and a small detour will lead us to the fortified village of Monteliscai, a castle of the Republic of Siena already mentioned in the 12th century.

The road that runs toward San Giorgio a Lapi is now free of traffic. On a small hill, near the church, begins a stretch of dirt road well known among professional cyclists, who ride it in the opposite direction during the "Strade Bianche" race. Special care should be taken during the dirt descent of Colle Pinzuto, which has very challenging stretches.

The Bozzone stream marks the arrival at the valley floor. Back on asphalt, we turn right, uphill, and then descend to the inner suburbs of Siena. Just over a kilometer separates us from Porta Pispini.

Itinerary curated by stradedisiena.it