Let’s start pedaling from the San Lorenzo, at the end of via Garibaldi, downhill, and then go up the hill overlooking the current railway station, the railway line and take the road that crosses the entire district of Sacciapensieri. where you can admire the Siena skyline. We are on the Capriola hill, and next to the convent stands the most important church among those found outside the city walls, full of history and it’s worth a stop to visit it: The basilica dell’Osservanza.

Once you have reached the Provinciale Chiantigiana, pedaling along a path uphill, to the left, after passing Ponte a Bozzone and San Giovanni, you reach Pianella. Immediately after the bridge over the Arbia stream, follow the signs to Montaperti, along the SP62 uphill for about a kilometer. We are pedaling along the ridge that separates the Chianti from the Crete senesi  the former with wooded areas and modern crops, fortresses and castles, land of crags, isolated houses, green stretches the latter, where we can admire a landscape that stirs your soul because its bitter beauty.

After passing San Piero in Barca and the detours that on the left, lead to Castelnuovo Berardenga, we always continue to pedal along a tilled track but not so challenging. We have reached Montaperti. The last kilometers of the itinerary pass through the centre of Casetta, Arbia (where you find a Leopoldine signpost from 1840), Taverne d’Arbia e Ruffolo.