Leave from Piazza Gramsci in Montaione and turn immediately left onto Viale Filicaja and continue on for approximately 800 meters until you turn right towards San Vivaldo. The first section is slightly downhill and then begins to go up during the last few kilometers to San Vivaldo. Go past the village of San Vivaldo passing in front of the Holy Mount of San Vivaldo ( a religious compound with monastery, church, and a series of chapels that guard some reproductions in terracotta from the life of Jesus Christ) and continue to pedal towards Castagno d’Elsa.
The road continues in gentle ups and downs in the green for about 7 km until you reach a junction where on the left there is a tabernacle of Christ. Then take the road to the right following the signs for Volterra – the main destination of your journey which is about 20 km from here – and just go past the village of Castagno d’Elsa. After about 350 meters, following the main road take a sharp turn to the right and begin to go down for 11 km until Molino d’Era. The first part of this descent is bordered by trees typical of the Mediterranean scrub, while the second section, the wildest and most barren, winds through the hills as far as the eye can see offering an unforgettable natural spectacle.
This long descent will give you the chance to prepare your breath in view of the arduous ascent to Volterra.
Having reached the end of the descent, cross the bridge over the river Era and you will come to a junction where you will turn left and follow the signs for Volterra which is about 9 km from here, all uphill. Although the first and short stretch seems to follow the valley floor, with a slope rather sweet and easy to pedal, after a few hundred meters it soon becomes clear that there is to sweat. The ascent begins to be irregular with some stretches of more than 20% of gradient! You should then get the right rhythm and ride with your head down until Volterra shows off with all its grandeur in front of your eyes. A visit here is absolutely required, not just to refresh yourself with a stop for lunch after all the ascents done, but also because this little town, with its old town and its traditions (Volterra is famous for its alabaster) represents a historical, artistic and cultural heritage among the most important in Tuscany.
Leave Volterra following the signs for San Gimignano and begin a descent of 3 km to the junction for Roncolla. Then the road goes up again, alternating short descents, ideal for breath and to see a landscape dotted with cypress trees and farmhouses that help draw the characteristic landscape of the Tuscan hills.
After 8 km from the junction to Roncolla, leave the main road turn left and follow thesigns to Castelfiorentino and Gambassi Terme. Here you will travel for 6.5 km riding the border between the provinces of Siena (right) and Pisa (left) until you reach the highest point of the entire route: 603 meters above sea level At this point you will enter the province of Florence, the road is downhill for 3.5 km to the junction with the road that to the right leads to San Gimignano.
Continue straight on in the direction of Castagno d’Elsa and then, following the main road, for Gambassi Terme. Once in Poggio all’Aglione, turn left towards Montaione to return to the starting point.