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Castellina in Chianti: A tour of the area

A bike itinerary that includes some of the Chianti's lesser known destinations

Discover some of the Chianti area's lesser known destinations with this cycling itinerary through vineyards and rolling hills.

Type of road: asphalt, gravel road
Type of bike: mountain bike, hybrid
For who: bike lovers
Departure and arrival point: Castellina in Chianti
Length: 36.99
Change in altitude: 695
Level of difficulty:medium

Note: This itinerary full of natural interest takes you on a path to discover the lesser-known part of the Chianti with stops at important artistic-historical sites like the Castle of Paneretta (10th century), the romanesque parish church of Cedda, the Castle of Strozzavolpe and the castle-village of Talciona (10th century), an important stop for pilgrims in the Middle Ages along the Via Francigena. From a technical point of view the path is difficult in that it has constant inclines and declines, though the relatively short course allows bikers to take their time with the hills.

Depart from Castellina and at the intersection of the main streets, 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 then a steep decline begins: at this point you need to pay attention 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 fountain with drinkable water and then turn left again where you will be confronted with a brief but difficult piece of road. When you arrive at thee large oak tree, turn left again until you arrive at a white street: turn right here through an area of vineyards, Mediterranean brush and pine, beech and oak trees. After 3km the asphalted road begins again and you 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 construction. Turn left on a white street that, shortly after, forks. Stay to the right and get ready to confront 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 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, leave the asphalt again and take the gravel road on the right following directions for the La Moraia agritourism.

Pedal along this path until you arrive at Talciona (with a great view of the Strozzavolpe Castle), a village which is known for its parish church. Another full kilometre downhill and then turn left on the asphalt road following the directions for Belvedere. Here the difficult climb begins, about 10 kilometres on a gravel road until you reach Castellina.