Among vineyards and hills in the Chianti region

This 36-mile (58-kilometer) looped bicycle touring route offers a challenging but rewarding experience, with significant climbs that require a good degree of physical fitness. Fortunately, your efforts are amply repaid by the spectacular landscapes of Chianti, encompassing both the provinces of Florence and Siena. The route runs through a combination of paved and dirt roads, making it ideal for gravel bikes or mountain bikes. For a more relaxed experience, you can even split the itinerary into three stages.

Set out from Tavarnelle, immediately facing a climb at a tad under 2 miles (or 3 kilometers) to the Castello di Tignano. The next stop is Poggibonsi, where you can take a restorative break and even visit the Forte Imperiale and Archeodromo. From Poggibonsi, take the provincial road of SP130 Castagnoli then continue to the Spedaletto junction. The dirt road climbs toward Bibbiano and Lilliano, skirting the Vallechiara Lake to Fonterutoli. This ancient castle is rich in history and legends, including that of the dispute between Florence and Siena, which was resolved thanks to a black rooster (“gallo nero”), today the symbol of Chianti.

Continue your journey to Castellina in Chianti, where you can stop for a second break. From here, the provincial road SP76 climbs to Macia Morta, the highest point of the route, offering panoramic views of the surrounding valley, rich in vineyards and forests. The subsequent descent leads to the Sanctuary of the Madonna di Pietracupa and the village of San Donato in Poggio, listed among I Borghi Più Belli d’Italia (The Most Beautiful Villages of Italy). After passing the Church of Santa Maria del Carmine in Morocco and the Romanesque Parish Church of San Pietro in Bossolo, return to Tavarnelle, the final destination of our itinerary.