On this side and that side of Val d’Elsa by bicycle

We start from the parking lot in Piazza Gramsci, in Montaione, taking Viale da Filicaja on the left and following the signs for Gambassi Terme and San Gimignano.

Towards the end of the uphill stretch, we come across an interesting archeological area with the remains of a Roman cistern dating back to the 2nd century AD. When we reach Gambassi Terme, we pass in front of the Municipal Park, then cross the historic center and head toward Certaldo.

After crossing the Elsa River, at the entrance to Certaldo we keep to the right at the first traffic circle and then follow the signs for Poggibonsi and Siena. Certaldo is certainly worth a stop, but we will revisit it later.

We continue on the State Road, a bit busier than other roads, but only for 2.5 km, until we turn left, following indication for San Donnino and Sciano. After a short, almost flat stretch, we begin to climb significantly, with a 15% ramp near San Donnino.

Arived at San Donnino, at the junction for Petrognano and Barberino Val d’Elsa, the distinctive dome of St. Michael the Archangel, built between 1594 and 1597, appears. This dome was commissioned by Giovan Battista Capponi at the site where the legendary Semifonte Castle was destroyed at the hands of the army of Florence in 1202. With its octagonal base, it reproduces on a 1:8 scale the most famous dome of Florence’s Cathedral, Santa Maria del Fiore.

We continue following the signs for Petrognano and Barberino Val d’Elsa, which we reach by a road that alternates between short climbs and rapid descents. After passing through the historic center of Barberino, we continue along a scenic ridge road that, continuing up and down, takes us first to Marcialla and then to Fiano.

After Fiano, a long and scenic descent begins, with some steep sections and tight turns that require attention but can make this part of the route exciting and fun.

At the end of the descent, here we are again in Certaldo. This time we take more time and, having left our bikes in Piazza Boccaccio, where stands a statue dedicated to the well-known fellow citizen, we take the funicular to visit the upper village, intact in its medieval structure. If you wish, just before arriving at Piazza Boccaccio, on the right is the road to go up to the village directly by bicycle.

We set off again, continuing on Via Cavallotti, taking a right at the first traffic circle and following the signs for Montespertoli-Castelfiorentino. After about 6 kilometers of beautiful flat road, we continue straight on at the crossroads, heading toward Castelfiorentino, a city that we come close to touching a few kilometers later. From here, unless you want to visit the town and make a short rest stop, turn left onto Via Ciurini until you reach a traffic circle. Take the first exit on the right and at the next traffic circle the third exit in the direction of Montaione, along a somewhat busy stretch on the outskirts of Castelfiorentino.

A few hundred meters later, we take a right, still in the direction of Montaione, to get out of traffic and tackle the last climb that will close the loop and make us return to the starting point.