Tuscany is a region devoted to cycling. In particular, the Chianti, hilly area with a small mountain range that separates Florence and Siena, lends itself to be traveled by bicycle through routes of varying difficulty.

Along these ancient streets, sometimes dirt, surrounded by nature, they pass through untouched landscapes and picturesque villages.

Vineyards, countries with castles and abbeys, but above all a dense network of dirt roads, make the Chianti, like other areas of Tuscany, a perfect place for simple trips, for beginners or children, for the athletic training of cyclists.

The routes can be practiced with racing bikes, hybrid bikes and mountain bikes, although the topography of the area lends itself to be traveled by mountain bike or good trekking bikes.

The white roads allow to keep a low speed and then to enjoy the view and the historical and artistic beauties that are encountered along the route. The ideal is to also stage the various wineries or farmhouses, where you can taste wine and typical products of Tuscan cuisine.

On these streets it was born the famous Eroica cycling event, a symbol of an epic cycling early Novencento. Let us see some ideas for visiting the Chianti by cycling.


The tour of the Chianti Classico encompasses villages like Volpaia, Greve, Gaiole, Castellina in Chianti, Montefioralle. In these areas there are monasteries and famous castles that dominate the hills, like the Castle of Albola, the Brolio Castle and the Abbey of Badia a Passignano.

Chianti Classico tour (185 km): Departure from Florence and the Florentine hills, you reach the village of Tavernelle Val di Pesa, then through the Val d’Elsa and you enter in the heart of Chianti Classico. Here you can visit the Abbey of Badia a Passignano and continue to Panzano in Chianti, Volpaia and Radda in Chianti. From here on, you encounter dirt roads of the Eroica path leading to the castle of Brolio and Gaiole in Chianti. Continuing you reach Greve in Chianti, and you return to Florence.

Eroica path: the Eroica is an event that evokes a cycling of the past, born in 1997 is still held in early October. The route runs mostly on dirt roads in the Chianti area, is clearly marked and you can practice all anno.I routes available are different depending on the degree of difficulty: the long one of 205 km, the walk 46 km, passing by the average 135 km and run 75 km. It starts from Radda in Chianti and touch the town of Castellina in Chianti, Volpaia, Brolio, Castelnuovo Berardenga, Pieve a Salti, Montalcino.

To learn more, visit the official website


Itinerary in the Val d’Orcia: For a tour of this lovely natural area you can walk the ancient streets of the Via Francigena starting from Siena and arriving in Buonconvento, including paved roads and dirt roads. From here you reach the medieval town of Montalcino where you can taste the famous Brunello di Montalcino.

It continues in the Monte Amiata area touching the fascinating Abbey of St. Antimo and you can reach the most characteristic villages: San Quirico d’Orcia, Pienza and Bagni San Filippo, where you can stop for a thermal bath. It then returns to Buonconvento and finally Siena.