A Guide to Chianti’s Historic Wineries to Visit During Your Stay

Chianti isn’t just about the scenery: it’s one of the world’s most important wine-growing regions, with wineries that embody centuries of Tuscan winemaking history. When you stay at Villa Bordoni, you’re in the perfect spot to explore some of the area’s most fascinating estates, where rural tradition, historic architecture, and, of course, great wines come together. Here’s a guide to the wineries worth visiting.

Borgo Castelvecchi

Just a few minutes from Villa Bordoni lies Borgo Castelvecchi, one of the most charming places in the area. The village, with its historic winery, combines wine production with the authentic atmosphere of a Tuscan village, with vineyards stretching all around the historic buildings.

Here, you can take part in guided Chianti Classico tastings and get an up-close look at the winemaking process, as well as visit the ancient cellar carved into the rock, which was once used for aging wine. It’s a perfect stop for anyone who wants to enjoy an authentic wine experience without straying too far from the villa.

Verrazzano Castle

Located in the heart of Greve in Chianti, Castello di Verrazzano is one of the best-known names in the area, linked to the family of the explorer Giovanni da Verrazzano. The estate has been producing wine for centuries and offers tours that include the vineyards, the historic cellars, and an area dedicated to the curing of locally produced cured meats.

The tastings here often pair wine, olive oil, and traditional Tuscan products, offering a complete experience of the region’s flavors.

Ama Castle

In the Gaiole in Chianti area lies Castello di Ama, an estate that combines winemaking with contemporary art: the village is dotted with installations by international artists, creating a journey that blends culture and wine tasting. It’s an ideal choice for those looking for an experience different from the usual winery tour.

Antinori in Chianti Classico

A short distance away, toward San Casciano Val di Pesa, stands the Antinori winery in the Chianti Classico region, a striking architectural project designed by star architect Marco Casamonti. The structure, largely underground and integrated into the hilly landscape, features a modern visitor experience that includes a panoramic restaurant and spacious areas dedicated to wine tasting. It’s a recommended stop for anyone passionate about contemporary architecture as well as wine.

Brolio Castle

The Brolio Castle, historically linked to the Ricasoli family—considered one of Italy’s oldest wine producers—is also located in the Gaiole in Chianti area. The castle, with its panoramic garden and medieval walls, offers one of the most beautiful views of the entire Chianti valley, as well as a wine-tasting tour that traces centuries of winemaking history.

Practical Tips for Visits

Many wineries require advance reservations for tastings, especially during the high season (April through October). Some estates, such as Borgo Castelvecchi, are located just a few minutes from Villa Bordoni and are ideal for a visit even in the late afternoon, allowing you to return to the villa in time for dinner.

For those who want to organize a full-fledged wine tour, it’s possible to plan two or three visits in a single day, alternating between large wineries and smaller, family-run estates, to get a complete picture of the variety of wines produced in the Chianti Classico region.

Guests staying at Villa Bordoni can also request personalized recommendations and assistance with booking wine tastings at partner wineries in the area.

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.