Beginning in Rosia, head south-west along the SP 73/bis “Senese-Aretina,” then turn left at the bar La Pergola onto SP 99 “del Piano di Rosia” on the left in the direction of Grosseto. After 100 m, we suggest stopping to visit one of the last active marble mills, which has an interesting exhibition on Broccatello, a priceless marble quarried in the Montagnola Senese.
Continuing for another 1 km, turn to the left towards Torri, which you can reach by following the cypress-lined road before turning to the right on via Carlo Costa; here, you’ll start a stretch of hairpin turns until you get to the fortified village. The town is worth visiting thanks to the presence of a medieval Vallombrosian abbey with a multi-coloured cloister. Turning back around at the crossroads with the SP 99, turn to the right and follow the signs for SS 223 “Siena – Grosseto”. Continue for about 1.5 km then go to the left towards San Rocco a Pilli. Leaving the paved road, pedal along a beautiful gravel backroad through the Piana di Rosia; after a few km, you’ll reached the next paved road, around a few country houses that were recently restored.
Continue straight on, traveling along a flat stretch at the beginning before two brief climbs up to the hamlet of San Rocco a Pilli (around 10 km). You’ll enter the town near Villa Cavaglioni and the parish church dedicated to St. Bartholomew. At the junction with via Grossetana, keep to the left and cross through the town. Go past the roundabout and continue in the direction of Siena for about 1.5 km.
Next, you’ll come to a crossroads, where you’ll turn to the left towards Carpineto, Barontoli and the “Poggio Salvi” farm. At the next junction, turn left again and pedal along a traffic-free road as it winds through the rolling hills overlooking the Piana di Rosia and the Montagnola Senese. At the fork for “Poggio Salvi,” the road will start a descent all the way until the small village of Cerreto Selva, flanked by vineyards of Sangiovese grapes, used to produce the area’s most typical wine, the Chianti Colli Senesi.
Once past the small village, near the fork in the road (about 15 km), go to the right to get to Volte Basse, where you’ll intersect with the SP 73/bis “Senese-Aretina”. Turn left and, after 300 metres, turn right in the direction of Sovicille, taking the SP 37. Leaving the village behind, pedal through the plain along a straight road, flanked by scenic pine groves for about 2 km until you reach the village Ponte allo Spino, where you will follow the signs for Toiano.
At this point, take a backroad that starts near farmed fields before transforming, after a brief climb, into a beautiful road surrounded by drystone walls, vineyards and olive groves and dominated from above by the imposing fortified farm called Palazzaccio di Toiano, made less daunting by the neighbouring 17th-century Villa Chigi, which sits at the edge of the oak and cypress forest, characterized by its noble design. Continue through Caldana until you get to the fortified castle of Poggiarello, before reaching a four-way crossroads: turn left and take the lower road as it winds between tall drystone walls all the way to the SP 37, near the 17th-century Church of the Compagnia della Madonna in Ponte allo Spino.
Continuing to the right, you’ll soon come to the harmonious simplicity of the Romanesque Church of San Giovanni Battista in Ponte allo Spino. From here, continue to the gates of Sovicille. Follow the signs for Rosia, which you’ll come to 4 km later.
- flag Sporty More demanding itineraries for highly trained cyclists and those who love a challenge, with the toughest climbs and hardest roads
- nature Scenic bike itineraries In the loveliest of places, immersed in nature, by the sea and through historical old towns
- location_city Urban itineraries Fascinating bike tours around the artistic treasures of Tuscany's major towns and cities
- wc Bike itineraries for tourists and for families Easy itineraries along the coast, in the hills and towns, suitable for families with children