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The famous Chianti Wine Route is one of the most traveled itineraries in Italy. The Chianti wines of the provinces of Florence and Siena, especially in the west of the Val di Pesa and Val d'Elsa, will be the focus of this tour. But not forgetting the historical and cultural highlights, you will travel through the land of the Etruscans, a land dominated by the Medici family, but where the Church also exerted its influence. Full of castles, fortresses, abbeys and churches, each with a wealth of works of art.
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The Chianti Classico area
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Chianti Classico used to be a very small area, as I told you in the accompanying article about wine tasting in the Chianti Classico area. Back then, we were talking about the towns of Radda in Chianti, Castellina in Chianti, and Gaiole in Chianti. Today, the area includes the towns of Castelnuovo Berardenga and Poggibonsi (in the province of Siena), San Casciano Val di Pesa, Tavarnelle Val di Pesa, Greve in Chianti and part of Barberino Val d'Elsa (all in the province of Florence). These towns make up the so-called DOC wine production area. Wine produced in this area can bear the name "Chianti Classico" (recognizable by the Gallo Nero or Black Rooster logo).
Geographically, Chianti is located between the provinces of Florence, Arezzo and Siena. You will also hear of Chianti Colli Fiorentini, Chianti Colli Senesi and Chianti Colli Aretini. The word colli means hills in Italian, so we are talking about the hills of Florence, the hills of Siena and the hills of Arezzo.
This itinerary through Chianti Classico is only 131 km/81 km long and starts south of Florence and ends in Monteriggioni. But believe me, it will take longer than you think. All the wineries, including some producing Super Tuscans, that are recommended for wine tasting are listed in the companion article. The map includes information on places of interest, restaurants and accommodation.
Greve in Chianti
Take the A1 highway, exit at Firenze Sud, cross the highway next to the Sheraton Hotel and follow the signs for SP-127, then SS-222 towards Grassina. Follow the SS-222 until you reach Greve in Chianti. First on the central square is the Town Hall, built in 1895 on the remains of a medieval palace dating from 1489.
On the opposite side of the square is the church of Santa Croce, also built in the 15th century, which contains some interesting works of art. The city is the center of a region dotted with churches, chapels, feudal castles, small medieval villages and country houses of Florentine noble families. Greve has a small but excellent museum with a fine collection of religious art. Don't miss the antique market on Easter Monday and the Flower Festival on the first weekend in May.
The annual Chianti Festival is held in September. Near Greve is the Castello di Montefioralle, which dates back to 1085 and is one of the oldest villages in Chianti, with picturesque streets and pretty facades. The village is surrounded by the original octagonal walls. Once there were two walls, but over the centuries the space between them was filled with houses, so little remains. Only the foundations remain of the four gates. Montefioralle was one of the largest military fortresses in this part of Italy during the Middle Ages. The fortress was destroyed in 1325, but was rebuilt in the 17th and 18th centuries.
Turn off the main road in Panzano
Following a side road off the 222, you reach the Castello di Panzano. Despite the traces of so much violence and human suffering over the centuries, the castle still retains many of the characteristics of the important fortress that it was during the wars between Florence and Siena. There are original records of the fact that Firidoli Ricasoli was the master of the fortress at that time, the same Ricasoli who previously occupied the Montegrossi Brolio castle. Where the church of Santa Maria stands today, you can still see the original castle walls. The old towers are now the bell tower of the church. Go through the domed gate and visit the tower house.
Take the road towards Volpaia
Following a side road, you reach Volpaia, a perfectly preserved medieval village built around a castle that once had to defend the border between Florence and Siena. Inside the castle is the interesting church of Sant'Eufrosino, where the so-called "Commenda" was consecrated.
An afternoon in Radda in Chianti
Further south is Radda in Chianti. The town is of Etruscan origin: traces of this mysterious people have been found in most of the villages in the area. In 1384 Radda became the capital of the League of Chianti, which also included the territories of Castellina and Gaiole in Chianti.
Radda has preserved its ring of ancient walls and has the elongated street plan of a typical medieval town. In the center is the Palazzo del Podestà, built around 400. Its façade is decorated with coats of arms, and the Church of San Niccolò. Nearby is the Franciscan convent of Santa Maria al Prato, which houses the headquarters of the Chianti Classico Consortium, founded in 1924.
Casa Chianti in Radda in Chianti
The monastery of Santa Maria al Prato now houses a wonderful museum of Chianti Classico, tasting rooms, halls for events, a bistro and a café. Definitely worth a visit.
Gaiole in Chianti
In 1300, with the proclamation of the Lega del Chianti, Gaiole became the capital, increasing the importance of the town, which was already known for its markets and the toll-house on the road to Siena. Between June and September, numerous markets and festivals are held, and the season ends in September with the harvest festival.
The area around Gaiole is rich in castles and farmhouses, and if you want to visit them all, you will need at least two weeks to do so; some are of great historical importance, while others are best known for producing Chianti wine. From Gaiole, head towards Siena to visit the impressive Brolio Castle. Brolio has always played an important role and has been the home of the Ricasoli family since the Middle Ages. The castle originates from the ninth century and was rebuilt by the Florentines in the 15th century.
Through the Chianti Classico vineyards to Monteriggione
Siena is worth a visit just by itself, if you don't have the time on this trip, make sure to visit it some time in the future. Just enjoy the large piazza where the famous Palio takes place in July and August and sit down for a meal in one of the restaurants on the map that we recommend.
Take the road to Siena and continue south through the Chianti Classico to Monteriggione, where our road trip ends, and you can drive back to over the highway to Florence. Built on a hill by the influential Sienese rulers, the town's walls and 13th-century structure are still intact and form the famous silhouette that many know from images of the Chianti region.
The houses within the walls surround the beautiful 14th century church. Today, only about two hundred of the original Monteriggians remain. The majority of the population works in the tourism sector, as is evident from the many artisan workshops, mainly for iron and lace. The famous silhouette of the village can be seen from the square. There is a restaurant in the square that serves typical Tuscan cuisine. It is well worth trying.
