Cycling in the Middle Ages along the roads of Valdelsa

The route along the roads of Valdelsa begins in Montaione, in Piazza Gramsci. We follow the signs for San Gimignano and take Viale Filicaja: after a short descent, a climb of about 3 km begins, passing by the archaeological site of the Roman Cistern and continuing until we reach the locality of Poggio all’Aglione.

At the next fork we keep to the right, still heading towards San Gimignano. After a last uphill stretch, the road will take us slightly downhill to the well-known medieval town, among rolling hills, fields of olive groves and vineyards (this is the area of Vernaccia di San Gimignano), country houses and rows of cypress trees; an area where human activities and nature blend in perfect balance.

San Gimignano welcomes visitors with its 16 towers and surrounding walls. A stop is a must to refresh yourself in one of its cafes and to visit the quaint medieval village, with its narrow streets, old stores and its 16 towers (of the original 72).

Having finished visiting the village, we take the road with signs to Ulignano and Cusona

This road descends for about 3 km until you turn left in the direction of San Benedetto. The road becomes narrower and with little traffic, and after 3.8 km you come to another fork, where you turn left. Shortly after, you pass the village of San Benedetto, leaving it on the right, to descend to the bottom of the Elsa valley, now on the outskirts of Certaldo.

We coast the Elsa River to enter the town from the bridge on Via del Molino. Once we reach Piazza Boccaccio, where the statue of the well-known fellow citizen stands, we can choose whether to tie up our bikes and ride up to the old town on the characteristic funicular railway or do it directly by bike. Whichever option you choose, a visit to the small medieval core, perfectly preserved, is certainly worthwhile.

Having resumed the previous road beyond the bridge on Via del Molino, we continue straight on, beginning an ascent with a few steep climbs, until we reach Gambassi Terme.

A short restorative stop in the small square of the village (if you still have energy you could make a short detour to visit the beautiful Romanesque parish church of Chianni, 700m north on the Castelfiorentino road) and here we are facing the last 2 km of uphill, until we reach the junction already passed at the beginning of the tour, where we will turn right to return to Montaione on a slight descent.