Leaving from Casole d’Elsa, follow the road for Monteguidi, which you will reach after an ascent of roughly 3km. From Monetguidi you go along the road that passes over the river Cecina and start to climb, gently at first then more steeply, towards the village of Montecastelli where you will cross into the province of Pisa.
From Montecastelli, continue on downhill towards Castelnuovo Val di Cecina. After 4km leave to road to Castelnuovo, turning left onto the winding road towards Radicondoli (12km): first you go downhill until you reach the bridge over the Lucignano stream, then start to climb again up the hill to Radicondoli, a charming medieval village with fantastic panoramic views far from any main roads.
From Radicondoli a fast and easy desent (2km) takes you down to a cross-roads where you turn left and follow signs for Messano (5.5km). From here, follow signs to Casole d’Elsa (8km), continue downhill before climbing for the last time to get back to the place you set off from.