Radda in Chianti: The Middle Ages, Wine, and Tuscan Serenity

If you’re riding a motorcycle through the Chianti region, there’s one place you simply can’t miss—and that’s a good thing: Radda in Chianti. The town sits on a hill offering sweeping views over the vineyards. This landscape is so quintessentially Tuscan that you almost wonder why every postcard isn’t taken right here.

History you can walk through

Radda has more to offer than just good lighting for photos. Its origins date back a long way, to the Etruscans, as archaeological finds show. Later, the town was the seat of the Lega del Chianti, a kind of medieval defensive alliance under the command of the Republic of Florence.

The heart of the town is Piazza Ferrucci, flanked by the Palazzo del Podestà with its historic coats of arms and the Church of San Niccolò, whose neo-Gothic façade seems almost a bit urban—unusual for a village of this size.

Between dry stone walls and underground wine pipes

A stroll through Radda feels like a journey back in time with a view: well-tended gardens, small stone houses, dry stone walls, and, every now and then, the scent of rosemary, earth, and fermenting grape juice.

The Castello di Volpaia, not far from the town center, is definitely worth a visit. Wine and olive oil are still produced today in this medieval castle, in old churches, cellars, and outbuildings that are connected underground via a so-called “vinoduct.” Volpaia is no longer an insider’s secret, but it has remained one of the most unusual and beautiful wineries in Tuscany.

A treat for wine and culture lovers

While in the area, it’s worth making a detour to the parish church of Santa Maria Novella, whose Romanesque origins remain clearly visible despite restorations. Those interested in sacred art should also visit the Church of Santa Maria in Prato, which houses a painting by Neri di Bicci, a master of 15th-century Florentine painting.

Right next door is the Casa del Chianti Classico, an interactive center dedicated to the region’s most famous wine, featuring exhibits, classes, and a small sensory trail. Even if you’re not a die-hard wine connoisseur, by the end you’ll understand a little better why this region is so obsessed with its wine.

Starting point for long and dusty tours

Radda is ideally located for exploring the rest of the Chianti region. From here, Gaiole in Chianti and Castelnuovo Berardenga are easily accessible—small towns that together form the heart of Chianti Classico.

If you love dusty adventures, you can follow in the footsteps of the legendary Eroica cycle route: a fantastic gravel route through Chianti that can also be enjoyed on a motorcycle and takes you back in time.

By motorcycle to Radda

• There are several ways to get to Radda; the most scenic route from Greve goes through Panzano and then along smaller roads—more winding and charming than any direct route—and takes about 35 minutes.
• There is parking outside the walls, right at the entrance to town; parking a motorcycle is no problem.
• The road to Castello di Volpaia is paved and easy to reach—it's well worth the trip.
• The Eroica route is gravel and dirt; it's doable with street tires, but not after it rains
• Radda is located at an elevation of 530 meters: it's noticeably cooler in the morning than in the valley, so don't forget your jacket

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