An Itinerary Through Villages, Vineyards and Postcard Landscapes
If you’re looking for an authentic way to discover Chianti, there’s no better base than Villa Bordoni. Nestled in the Tuscan countryside between Florence and Siena, the villa is the perfect starting point for exploring the area’s historic villages each morning and returning in the evening to unwind among the hills. Here’s a two-day itinerary designed for guests staying with us who want to experience the real Chianti.
Day 1: Greve in Chianti and Panzano
Morning
From Villa Bordoni, it’s about a twenty-minute drive to Greve in Chianti, one of the liveliest towns in the area. The heart of the town is Piazza Matteotti, a funnel-shaped square surrounded by porticoes and historic shops. It’s worth stopping at one of the local butchers or wine bars for a first taste of Tuscan cured meats and Chianti Classico.
Don’t miss the Church of Santa Croce, home to religious artworks, and a stroll through the side streets lined with small craft shops and local products.
Lunch
Greve has several trattorias serving traditional Tuscan cuisine: pappa al pomodoro, ribollita and, of course, bistecca alla fiorentina, paired with a good glass of local wine.
Afternoon
In the early afternoon, head to Panzano in Chianti, just ten minutes from Greve. Panzano is famous worldwide for the Cecchini butcher shop, but it’s worth visiting for the view alone: the village sits on a hilltop overlooking the Conca d’Oro, one of the most striking vistas in all of Chianti.
From here you can continue with a short walk among the surrounding vineyards, perhaps stopping at one of the local wineries for a guided tasting.
Evening
Return to Villa Bordoni for dinner, perhaps choosing one of the wine and food experiences organized directly at the villa, to end the day without getting back in the car.
Day 2: Radda in Chianti and Castellina in Chianti
Morning
The second day is dedicated to two of the most authentic villages in Chianti Classico. Head towards Radda in Chianti, about forty-five minutes from Villa Bordoni. Radda has kept its medieval layout intact, with the historic center gathered around the Palazzo del Podestà , recognizable by the stone and ceramic coats of arms of the families who governed it over the centuries.
Walking along the patrol path that runs around the village offers a magnificent view over the surrounding hills and vineyards.
Lunch
Radda has excellent wine bars serving food, perfect for a light lunch paired with a glass of Chianti Classico Gallo Nero, the symbol of the consortium that protects these wines.
Afternoon
In the afternoon, head to Castellina in Chianti, another fortified village that preserves a fascinating underground Etruscan passage, the Via delle Volte, once used for safe movement during sieges. It’s also worth climbing up to the fourteenth-century fortress for another panoramic view over the Tuscan countryside.
Those with time can stop at one of the historic wineries along the way back for one last tasting before returning to Villa Bordoni.
Evening
A final dinner at the villa, perhaps with a closing toast over a good glass of Chianti, to celebrate these two days among the most beautiful villages in Tuscany.
Practical Tips
The roads between the villages pass through some of the most photographed landscapes in Chianti: it’s worth bringing a camera and taking your time with a few stops along the way.
The villages on this itinerary are all between twenty and fifty minutes by car from Villa Bordoni, making it easy to visit them comfortably in a day and always return to the villa for the night.
We recommend booking in advance for tastings at the most well-known wineries, especially during peak season and the harvest period, between September and October.