Chianti villages West – road cycling

Imagine a perfect day on a full carbon Pinarello or Bianchi road bike, cycling on some of Italy’s most iconic roads, past vineyards, olive groves and cypress trees. Roads and panorama which have been immortalized in Giro d’Italia and in Strade Bianche by pro riders.

The Chianti Classico area is a perfect area for enjoying road cycling at its finest, this is why many pro riders are based in this area, as there is something for everyone: gradual climbs, hairpin turns, white knuckle descents, flats, grueling accents – in Chianti Classico there is a certain rythym to the road biking, here is your opportunity to be drawn to its captivating allure. You may never wish to leave again, just like us.

This ride allows you to explore the three most charming medieval wine villages in Chianti: Gaiole, Radda and Castellina. They constituted the “League of Chainti” in the Middle Ages and today are lovely tourist destinations related to fine wines.

The ride starts in Gaiole in Chianti, a quiet and very beautiful wine village, as well as home to the world famous vintage bike race called L’ Eroica.

We bike south towards Siena on the Chiantigiana road, then continue on a gradual, very scenic climb to Radda in Chianti surrounded by vineyards on all sides. Then, prepare your legs and mind for the steep 15% 1 KM ascent into the city centre of Radda. You will have earned your wings and the incredible 360 degree panorama from one of Tuscany’s most charming medieval wine villages, looking out onto the surrounding Chianti countryside.

Afterwards, we will give our legs a break, and unwind on a lovely ridge road connecting Radda to Castellina.

Then there is time for an optional stop for lunch (not included in the tour price) at the flagship winery restaurant or other nearby bars and trattoria located in downtown Castellina.

We will also enjoy a wine tasting at one of the area’s most prestigious wine estates, of their best wines and vintages.

Later on, we continue by bike, on a very long and memorable descent, and loop back around towards Radda once again.

The last leg of our journey retraces a small portion of L’Eroica vintage bike ride, climbing on a switchback filled road, through shady woods, on the way to Badia a Coltibuono. Then, a final 5 KM, exhilarating decent back to Gaiole in Chainti.