Cycling in Chianti, from Barberino Tavarnelle to Castellina and Radda in Chianti

If you are looking for a not-too-demanding itinerary among the Chianti vineyards, here is the one for you!

At just over 42 miles (68 kilometers), this route runs entirely on paved secondary roads between Val di Pesa and Val d’Elsa, thus suitable for Gran Turismo bikes. To make it even more enjoyable, you can split the itinerary into multiple stages.

Start from the village of Tavarnelle and immediately reach that of Barberino, entering through the ancient gateway of Porta Fiorentina. As of 2019, these two villages have been unified into the municipality of Barberino Tavarnelle. Leaving via the Porta Senese, continue in the direction of Poggibonsi to the municipal stadium, where an initial rest stop can be made.

From here, follow the SR429, the regional road that takes you to Castellina in Chianti. Not too challenging, this climb is to be enjoyed entirely for the splendid views. Along the way, stop to admire the Prish Church of Sant’Agnese in Chianti, at the entrance to the beautiful Sant’Agnese Forest Nature Reserve. Once you reach Castellina in Chianti, you can take the opportunity to recover and enjoy some refreshments.

Back on your bike, continue to Radda in Chianti, the ancient capital of the medieval alliance of Lega del Chianti (League of Chianti). Entering the historic center from Porta Fiorentina, you pass by the Palazzo del Potestà and the Church of San Niccolò, to the Porta Valdarnese, which introduces you to the last section of the route and the most challenging one.

In fact, follow the descent to the village of Lucarelli and from there, cross the valley of gold along the Pesa River. Traveling along the SR222, this regional road will take you to the villages of La Piazza and Sicelle, to the Madonna di Pietracupa Sanctuary, not far from the medieval village of San Donato in Poggio, one of the most beautiful villages in Italy.  

From here, return to Tavarnelle via the Carmelitane Scalze Monastery.