Cycling in Tuscany

Castellina in Chianti (578m) – Castagnoli (427 m) – Bivio Talciona (150m) – Church of Sant’ Agnese (410m) – Castellina in Chianti

Distance: 41km

Time: 4 hours

Road surface: Unpaved for about half the ride, then on quiet asphalt roads.

Difficulty: Requires average athletic preparation. Several steep ascents of medium intensity in the re-ascent to Castellina.

Route: This mountain-bike ride starts and finishes at Castellina in Chianti via the State Road for Poggibonsi. After 2km turn off for the castle at Castagnoli. When the asphalt ends, the wide dirt road descends into lovely countryside, with views across the Staggia and Elsa valleys.

Soon, you’ll come upon several hairpin bends; take great care because it’s easy to lose your balance on the very steep slope and gravel roadbed. Close to Villa Rosa and Gretole, the route appears to follow flat ground yet crosses a ridge with views across the fields. Continue on asphalt until reaching a crossroads signposted for Talciona.

After looking around Talciona, return to the crossroads and head uphill to admire the little presbytery of Santa Maria, which has an architrave sculpted in 1234, bearing a rough but charming Adoration of the Magi. Continue uphill along the little asphalt road that soon becomes a track, in the direction of Villore. The unpaved road meets the State Road from Poggibonsi on a bend. Here, head towards Castellina to finish the ride.

Fattoria San Michele (847m) – Volpaia (617m) – Dogole (625m) – Badiaccia a Montemuro (706m) – Fattoria San Michele

Length: 14km

Time required: 4 hours 30 minutes

Road surface: Mainly tracks and a short stretch of asphalt.

Difficulty: Average physical challenge. Be very careful on the Volpaia to Dogole stretch, because it is unmarked and becomes tricky near Dogole.

Recommendations and notes: The signposts are old and several segments of road are unmarked. Take a map, preferably to 1: 25.000 scale, and plot the following instructions on it.

Ideal season: All, except very rainy periods, during which the ground becomes very muddy.

The route: From Greve in Chianti, ascend Monte San Michele on the smooth dirt road to the wine estates of Melazzano and Caprolo, enjoying panoramic views of the countryside as you go. Your first stop is the ruins of the medieval presbytery of the church of Santa Maria.

Continuing towards the summit of Monte San Michele (892m), the highest peak in Chianti, cross the road that ascends from Lucolena, climbing continually until you reach the nature reserve at San Michele and the entrance to the estate of the same name.

On leaving the San Michele estate, continue in a southerly direction along the edge of the fields. At the first crossroads, turn off the track and bear left, continuing straight and descending slightly. This is CAI path 30 and 32. At Poggio Sereno you’ll pass through lush pine woods, followed by bush-covered and open terrain.

On reaching a crossroads, continue in the direction of Lamole, ignoring CAI path 30, and head south on the same level as far as Poggio Querciabella. Here, a steep shortcut on the left makes it possible to descend to the dirt road that leads from Panzano to Volpaia, which can be seen amid the crops.

Visit Volpaia then set off along the old mule track to Badiaccia, constantly descending. The route keeps to the left of the valley until it crosses a ditch, then starts to climb through dense woods to the abandoned houses of Dogole. The ancient path here is covered with branches as far as the ditch below the Lungagna house, from where it becomes smooth again, all the way to Badiaccia a Montemuro.

Travel across a few hundred metres of asphalt on the quiet provincial road leading to Lucolena, until the beginning of CAI path 9 appears on the right. Exactly opposite is a track that ascends to roam the southern slopes of Monte San Michele, before returning back to the first crossroads encountered after leaving the San Michele estate.