Medieval charm, wine and Tuscan calm
If you’re riding through the Chianti hills, chances are high you’ll come across Radda in Chianti – and that’s something to look forward to. Perched on a hill and surrounded by vineyards, this charming village is a picture-perfect representation of Tuscany’s heartland.
History you can walk through
The roots of Radda go deep – from Etruscan settlements to medieval strongholds. For some time, it was the headquarters of the Lega del Chianti, a Florentine alliance to protect the region.
At the town’s core lies Piazza Ferrucci, flanked by the historic Palazzo del Podestà and the church of San Niccolò, with its striking neo-Gothic façade. Yet just around the corner, peaceful alleys and stone houses transport you straight back to a quieter time.
Between dry stone walls and underground wine pipes
A stroll through Radda offers more than just pretty views – it’s a sensory experience of rosemary, vineyards, and sun-warmed stones.
Don’t miss the Castello di Volpaia just outside the town. Still a working winery and olive oil producer, it hides its cellars in old churches and medieval buildings, all cleverly connected by a curious underground “vinoduct”.
A treat for wine and culture lovers
Nearby, the church of Santa Maria Novella stands as a fine example of Romanesque architecture, despite several restorations. And the church of Santa Maria in Prato houses a beautiful Madonna and Child by 15th-century painter Neri di Bicci.
Next door, you’ll find the Casa del Chianti Classico, an interactive space to dive into the world of Chianti wine – complete with exhibits, tastings and sensory walks.
A perfect base to explore Chianti
From Radda, other gems like Gaiole in Chianti or Castelnuovo Berardenga are just minutes away. Adventure seekers can follow the route of the Eroica, a vintage cycling race that winds through the unpaved roads of Chianti, the Crete Senesi and the Val d’Orcia – an exciting ride, even on two motorized wheels.
In short:
Radda isn’t just a stopover. It’s a place to slow down, sip slowly and enjoy life – whether you’re strolling the streets or leaning on your parked bike, soaking in the view.


