Start from Piazza Gramsci in Montaione and head towards Piazza Cavour, then pass in front of the War Memorial and go along Viale Italia and travel along the ancient walls of the castle of Montaione. Go straight on towards San Miniato starting a descent of 5 km through the town walls to the bridge on the river Egola. After crossing the bridge turn right towards San Miniato.
The road, flat, stretches for 8.5 km in the valley of the river Egola giving you the opportunity to properly warm up your legs and get ready for the ascents ahead. Go past the towns Casastrada and Corazzano up to a junction where, leaving the main road, turn right to San Miniato. The road narrows and begins to go up among some hairpin turns for about 1.2 km and then goes down again and arrives at a crossroads. Then you have to take the road to the right and keep following the signs to San Miniato. Begin to go up for 2.5 km until you will pass in front of the first houses of San Miniato.
Cross the village – famous in Tuscany for its white truffles and the tower of the Rocca di Federico II – through the narrow streets of the old town until piazza Buonaparte where you have to turn right onto Via Paolo Maioli until Piazza XX Settembre. From here you will continue along Via Francesco Ferrucci and moving away from San Miniato continue for 3 km among short ascents and descents until you reach a junction. Here, leaving the main road, keep to the right in the direction of Castelfiorentino and continue to pedal on the ridges of the hills enjoying the view over Valdelsa that you can enjoy from here.
Once in the valley floor continue to travel on a flat road until you come to a crossroads, where you have to turn right onto Via Curiel following the signs for Castelnuovo. Here starts a short steep ascent for about 1.5 km that will take you directly to Castelnuovo: an ancient medieval village whose walls (dating from the XII century and now destroyed) surround the church of Santa Maria Assunta and the Church of Santi Lorenzo e Barbara. Continue to go up gently to the beautiful parish church of San Pietro e Paolo in Coiano: a church dating back to 1029 and cited by Sigerico, the Archbishop of Canterbury, describing it as one of the stages of the Via Francigena that he used to travel to go to Rome.
From here, a short but steep descent will take you up in the valley of the River Orlo where you have to turn left in the direction of Castelfiorentino which is approximately 7 km from here. At the traffic lights turn right and after 1.2 km at the first roundabout take the road on the right, and after 800 meters turn right again towards Montaione. Go along Via delle Colline for 7.5 km until you get to the starting point in Piazza Gramsci in Montaione.