Set out on a cycling journey through the iconic hills of Chianti Classico, where vineyards, cypress-lined roads, and ancient villages create a landscape famed around the world. This tour invites you to discover the region’s rich heritage at your own pace, following scenic dirt roads that wind through the heart of Tuscany.

Your adventure begins with a ride to Fonterutoli, a historic village deeply connected to the centuries-old rivalry between Florence and Siena. Here, you can pause to sample Chianti Classico wines produced in the surrounding vineyards, immersing yourself in the local winemaking tradition. The route continues to Castellina in Chianti, a charming hilltop town, before reaching Monteriggioni, a perfectly preserved medieval castle that stands as a testament to the area’s storied past.

Throughout the tour, you’ll enjoy panoramic views, gentle climbs, and the freedom to stop for tastings or a traditional Tuscan lunch at local farms. The experience concludes back at the starting point, leaving you with lasting memories of cycling, history, and the flavors of Chianti.