Cycling through historical towns: from Colle Val d’Elsa to San Gimignano and Radicondoli

Setting out from Colle Val d’Elsa, head along the S.S. 68 which goes to Volterra. After around 3km, when you reach Le Grazie, bear right heading towards San Gimignano (11km). From here, there are a series of climbs and descents on the approach to San Gimignano castle. When you reach the castle, turn onto the S.S. 68, bearing right (towards Volterra) for 3km until you reach a turn off on your left for Casole d’Elsa, which is a 10km ride from here.

From here, the route takes you towards Monteguidi (6.5km, with a 3km final uphill stretch). You’ll then head downhill and cycle along the road which crosses the River Cecina and then starts to climb gently. The incline then becomes steeper on the approach to the village of Montecastelli, which borders with the province of Pisa. From Montecastelli, continue heading downhill towards Castelnuovo Val di Cecina. After 4km, turn left off the road for Castelnuovo, heading down the windy road which heads to Radicondoli (12km). You’ll first drop down towards the bridge which crosses the brook at Lucignano, before heading back up the hill of Radicondoli, a charming medieval village cut off from the main transport routes which offers stunning panoramic views.

Heading out of Radicondoli, a short and pleasant downhill stretch (2km) brings you to a crossroads where you’ll bear left following the signs for Mensano (5.5km) and then Casole d’Elsa. Before reaching the village, turn right following the signs for Colle Val d’Elsa. After 4km, at the T-junction which intersects with the S.S. 541, turn left, which brings you back to your initial departure point (11.5km) on the cycle path on the main road running parallel to the River Elsa.