19.7 Km / 250m D+ / 380m D-

Gaiole in Chianti, the start of an epic journey. Through soft hills and vineyards, the climb to Brolio Castle immerses you in history and mystery. A gravel descent through vineyards and the majestic oak are just the beginning of an adventure full of surprises.

Cycling towards Castelnuovo Berardenga, where castles and abbeys tell tales of ancient history, the route leads near Siena. Don’t miss the chance to visit the city and be enchanted by its Duomo and the iconic Piazza del Campo.

From Colle Malamerenda, the road opens towards Val d'Arbia. Through rolling hills, fields, and historic villages, the route intersects with the Via Francigena, leading to unique discoveries like the village of Radi and the ancient Etruscan site of Murlo.

Between Bibbiano and Montalcino, one of the most challenging stretches awaits, surrounded by Brunello vineyards. The famous Castiglion del Bosco climb offers breathtaking views and leads you to the majestic town of Montalcino, the home of Brunello.

Before leaving Montalcino, host of the spring edition of L’Eroica, enjoy the breathtaking view over Val d'Orcia from the Giardini dell'Impero. A stop at the medieval fortress and a glass of Brunello are the perfect prelude to a scenic descent through vineyards and white roads.

Leaving Torrenieri, you ride through gentle hills to Cosona and Lucignano d’Asso, then reach Pieve a Salti, a leader in organic farming. Don’t miss visiting Buonconvento, one of Italy’s most beautiful villages, where time seems to stand still.

From lush vineyards to the Crete Senesi, a unique landscape unfolds with gullies, clay hills, and isolated farmhouses. These breathtaking views lead to Asciano, a village rich in history and tradition, where Tuscan flavors meet timeless beauty.

Leaving Asciano, you tackle the “queen” of L’Eroica: the Monte Sante Marie white road, with its tough climbs and descents. From here, you return to Chianti, passing through Castelnuovo Berardenga, where the Chianti hills meet the Crete Senesi.

Castelnuovo Berardenga, a place steeped in history and epic battles like Monteaperti, recounted by Dante. Just a few kilometers away, the commemorative pyramid stands amidst ancient cypress trees. The route continues towards Vagliagli, with varied landscapes and gentle climbs.

The climb towards Vagliagli is a journey through vineyards and shaded woods. At Dievole, L’Eroica cyclists stop for a legendary refreshment, while near Vagliagli lies the Chianti Sculpture Park, an open-air museum perfectly integrated with nature.

The route winds along the Arbia River to Radda in Chianti, a village rich in history with ancient walls and stunning views. Walking through the medieval streets of this historic stronghold of the Chianti League feels like stepping back in time.

Starting from Radda in Chianti, the route passes through the “Bosco del Chianti,” a unique natural setting with a rich history. After an unforgettable descent, the path leads to Gaiole in Chianti, passing through the charming village of Vertine.

Monteroni d'Arbia, a village born around its medieval mill and the Grancia di Cuna complex. The route winds through the Sienese clays to reach Asciano, offering breathtaking views and a deep dive into Tuscany's millenary history.

The route variant leads to Panzano and Volpaia, where a legendary stop awaits with ribollita. After a refreshing break at Poggio delle Stanche, the journey continues towards Greve in Chianti, dominated by the impressive Verrazzano Castle and its rich historical past.

Castellina in Chianti, with its imposing Rocca, welcomes cyclists into the heart of Chianti Classico. A village rich in history, with Etruscan origins and ties to the Chianti League. The charming Via delle Volte offers a cool and fascinating escape from the summer heat.