This route will lead you through the heart of the Montagnola region and is entirely on quiet roads with little traffic. It is an undulating route, with two fairly long hilly sections.
Point of departure and arrival: Sovicille
Level of difficulty: challenging
Distance: 50 km
Total climb: 610 m
Type of road: asphalt
Type of bike: all terrain, road bike
The route starts from piazza Marconi in Sovicille, from where you will come to a roundabout at the end of the road. Here, turn left on the SP 37 “Sovicille” road towards Siena - Volte Basse, which goes downhill at first through the Piana dello Spino area where, after 1.7 km you will see the church of San Giovanni Battista on the right hand side. Continue along the SP37 towards Volte Basse, riding alongside a long strip of pine trees on the right. When you get to a T-junction with the SP 73 “Senese Aretina” road turn left towards Siena, and after 300 m turn left again onto the SP 101 “Montemaggio” road towards Florence – Monteriggioni and you will find yourself in the municipality of Siena.
Continue along the gentle hills of the road and after 11.7 km you will get to Pian del Lago. At the junction near the Pian del Lago riding club, turn left towards Celsa castle. After 3 km you will be back in the municipality of Sovicille, where a pleasant uphill climb starts. The surrounding landscape is beautiful and the road runs through oak woods, olive groves and fields until Celsa castle (XVII century). At the iron gate you will enter the municipality of Casole d'Elsa: continue uphill for another 1.6km until Celsa (573 metres above sea level). After the hill you can, if you want, make a short detour to the town of Marmoraia.
The track here is an important watershed between two rivers (the Arno and the Ombrone). Once back on the SP 101 follow the narrow path downhill (be careful), which has beautiful views reaching, on clear days, as far as the Apuan Alps and Chianti.
After 4.7km, shortly before the town of Scorgiano, turn left towards Pievescola, which you will get to after a hilly road of just under 5km. Pievescola is famous for its autumn mushroom festival and for the church of San Giovanni Battista in the centre of the town. At the roundabout in front of the “Fungo Innamorato” park continue along the SP 52 “Montagnola Senese” road towards Ancaiano – Sovicille. After 4.2km uphill you will get to the small village of Simignano, the real heart of the Montagnola region, where you will see Cinta Senese pigs grazing in the woods.
Continue uphill for 1.8km until Passo dell'Incrociati (505 metres above sea level), and from there the road goes downhill and has several sharp hairpin bends. Just before the end of the downhill stretch you will go through the village of Ancaiano, where the architect and painter Baldassarre Peruzzi was supposedly born. He designed the local church of San Bartolomeo. From here continue towards Sovicille, passing along the edge of beautiful Sangiovese vineyards on the Trecciano estate and near a rectory dedicated to San Michele Arcangelo, surrounded by olive trees.