The region of Italy known as Chianti covers a large portion of Tuscany, from south of Florence down to Siena. Wine has been produced in this area for the last 1000 years. Many towns fall within this region, but at its heart is a small section which includes the original Chianti villages of Radda, Gaiole, and Castellina plus the town of Greve (all four villages have since added the qualifier “in Chianti” to their official town names). The wines from this small area are the ones designated as Chianti Classico. They use the Gallo Nero (Black Rooster) symbol that is the mark of the highest quality DOCG Chianti wines.

I’ve visited the Chianti region on day trips over the past few years, each time exploring one or two of the villages and wineries of the Chianti Classico region and enjoying the remarkable scenery of the area. Recently, some friends and I went for a day-long drive that included the village of Radda in Chianti and its small “suburb” of Volpaia.

Radda sits high on a hilltop with valleys on either side, giving it panoramic views in nearly all directions. A historically important place, Radda was once the capital of the Chianti region and the seat of the Lega del Chianti (Chianti League). Its fortifications provided a defense during the ongoing conflicts between Florence and Siena. Despite those defenses, much of the town was destroyed during a battle in 1478. It was rebuilt in a medieval plan and today it retains that historic character with winding streets, small piazzas, a church on high, and parts of the fortified wall still visible. The central piazza faces the Palazzo de Podestà (Municipal Building) with its small logia and facade covered with family shields.

Across the piazza is a lion-head fountain with townhouses and the church of San Niccolo up above.

More modern touches include a variety of shops, wine bars (an ideal place to savor a glass of Chianti Classico wine), restaurants and gelato spots. It’s a good place to wander, following wherever the streets take you. Outside the historic center are scenic overlooks and a pretty city park.

From Radda it is only a short drive to the 11th century hamlet of Volpaia. This is a tiny town with only about 50 permanent residents. As part of the commune of Radda, Volpaia also produces Chianti Classico wine. In fact, the family owned Castello di Volpaia Winery is the major presence here, with over 900 acres of land producing wine, olive oil, and vinegar. I didn’t have a chance to visit the winery or its shop on this day - I’ll save that for a future visit.

The village itself is a medieval jewel box. Like many other small villages in Tuscany there are defensive walls, watch towers, and a castle but somehow the town has a character all its own. Quiet, pretty, meandering, historic, a bit mysterious. What lies behind those old wooden doors and windows? What echos of history are to be found inside the castle walls? Who tends that pretty garden? I found a photo opportunity around every corner in Volpaia. Some of my favorites are below.

After such a long period without travel in the age of the virus, the simple joy of a day trip to a beautiful area, the chance to wander through these small villages, a good meal (with a glass of Chianti of course), a mild fall day shared with visiting friends - these things feel like a gift and a blessing.