The starting point of this journey really needs a visit. The imposing 14th-century fortress tells you immediately about the urban layout of Montalcino, a medieval city with a military structure of straight, steep streets, behind which hide some true masterpieces like those kept in the Museum of Sacred Art, home to one of the richest collections of painting and wood sculpture from the Sienese School.
There are numerous churches, but a few stand out: the 14th-century Sant'Agostino, the Neoclassical cathedral, the Sanctuary of the Madonna del Soccorso and Sant'Egidio, 'the church of the Sienese'. The 13th-century Palazzo Comunale, a slender but sturdy structure, stands alongside a tall bell-tower, really almost a watchtower topped by a 'campanone' (big bell) and which surveys the whole area.
From Montalcino we cycle in the direction of Sant'Angelo in Colle until the road forks to the right for Castiglione del Bosco. We descend for a kilometre until we get to another junction, ignoring the deviation for Tavernelle on the left and continuing on the wide white road towards Castiglione del Bosco.
We keep going this way for another 4km until the next junction, where we take a left for the castle of Castelgiocondo, around which, in Quercecchio, you can see thousand-year-old holly oak trees. Passing the castle, we continue to descend until we reach the wineries of the Castelgiocondo company.
The road winds among olive trees until meeting (on our right) the small farm of Corrione, where we continue in straight descent; beyond a ditch, which is occasionally the bed of a stream but is almost always dry, we follow a long line of cypresses before reaching a junction. This leads onto a poor tarmac road for Tavernelle, while we bear left in a gentle climb.
Close to Tavernelle, under the sign for the winemakers Banfi, we bend to the left between two vineyards. Then we take the junction to the right for the Monali farm, rising to a straighter road through the woods which passes close by the agriturismo hotel Brizio.
We continue to climb until we reach a wider road, where we take a right and then another right immediately afterwards, bringing us to the little farm of San Lorenzo. From here we make one last demanding push to the 'Mountain Pass'road, where we bear left until we get to Montalcino.
In case you're feeling full of energy at this point, you could consider extending this itinerary and continue your ride up until the renowned Abbey of Sant’Antimo. Set only nine kilometres south of Montalcino, in the direction of Castelnuovo dell’Abate, the abbey is a monumental, solitar 12th-century temple that is considered one of the best examples of French-Romanesque architecture in Italy.
- 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