Depart from Castellina and at the intersection of the main roads, SS 222 and SS 429, take the asphalted road towards San Donato, pedalling up hill along the trail of Macia Morta, which offers panoramic views of the Val d'Elsa and Poggibonsi. After about 3.5 km, the road begins to descend and a steep decline begins; at this point you need to look out for the left turn which will take you towards Olena (about 6 km from Castellina).
Continue along the gravel road, through the town of Olena, near a drinking fountain and then turn left again where you'll be confronted with a short but difficult bit of road. When you arrive at a large oak tree, turn left again until you get to a gravel road. Turn right here through an area of vineyards, Mediterranean brush and pine and beech and oak trees. After 3km, the asphalted road begins again and you'll continue towards the Castle of Paneretta and the town of Monsanto before arriving at the bottom of the valley crossing the Siena-Firenze highway. The descent ends here at the level of an old abandoned building. Turn left on a gravel road that, shortly after, forks. Stay to the right and get ready for a major ascent to arrive at the village of Somano and, after another kilometre, the asphalt road of SS 429.
Continue to the left, heading slightly uphill towards Castellina and past the romanesque parish church of Cedda, which is worth a visit. About 2.5km after taking SS429, near the Melini vineyards where the woods start again, come off the asphalt road and take the gravel road on the right following directions for the La Moraia agriturismo.
Pedal along this path until you arrive at Talciona, a village which is known for its parish church and boasts a great view of the Strozzavolpe Castle. Another full kilometre downhill and then turn left on the asphalt road following the directions for Belvedere. Here, a difficult climb begins for about 10 kilometres on a gravel road until you reach Castellina.
- 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