Adventures on gravel roads: from Radda and Castellina to Vagliagli

A looped itinerary passing vineyards, castles and ancient Etruscan sites, touching the towns of Radda in Chianti and Castellina in Chianti as well as the village of Vagliagli in Castelnuovo Berardenga.

The 38-mile (61-kilometer) route on largely unpaved roads is suitable for gravel bikes and MTBs. With a rise in elevation of 4,134 feet (1,260 meters), it is certainly challenging but the beauty of the roads and landscapes make it incredibly fascinating.

The start and finish are in the village of Radda in Chianti, the former capital of the Lega del Chianti (Chianti League), the historical Florentine military alliance. You set off along a dirt road following the Strada della Croce until reaching the SR222 Chiantigiana road that climbs through woods and vineyards to 2024 feet (617 meters) before descending to Castellina in Chianti. Here you can stretch your legs while visiting the village with the charming Via delle Volte, an ancient walkway designed by Filippo Brunelleschi.

From Castellina, set off once again in the direction of Castello La Leccia, alternating between dirt and gravel roads until getting to Quercegrossa. It is here that the most challenging part of the route begins, with a climb that leads to the village of Vagliagli at 1650 feet (503 meters). 

Now, continue to Poggio Serravalle, passing near the ancient Etruscan Necropolis of Poggino. At the locality of Croce Fiorentina, descend to the junction with the Eroica route that will take you back to Radda in Chianti.