14 Best Things to Do in Chianti Region, Italy

Chianti is certainly one of the most beautiful and famous areas in all Tuscany. It is located in the center of Tuscany, among the provinces of Florence, Siena, and Arezzo. The territory is a succession of rolling hills, characteristic villages, ancient fortresses, churches, and country houses. Living the Chianti means immersing yourself in this evocative atmosphere, visiting the many towns, relaxing in the countryside, dedicating yourself to the pleasures of the table, and good wine. Nature is the protagonist in Chianti and is enriched with historical places, monuments, museums, and traditional events. A suggestive nature-rich not only of beauty and history but also of unique food and wine products that have made this region famous all over the world, such as its famous wine. The Chianti wine area is in fact among the most renowned.

Best Things to Do in Chianti

Greve in Chianti

Greve in Chianti

You can discover Chianti starting from Florence, taking the SS 222 road towards Greve in Chianti. The town is one of the gateways to the Chianti area and is worth a visit. This lively town is famous for its particular square, which since the Middle Ages was the most important market in the whole area.

The square, almost triangular in shape, is flanked on three sides by large arcades, which shelter from the rain and sun during shopping. In the center is the statue of Giovanni da Verrazzano, discoverer of the Bay of New York. In the narrow part, there is the medieval church of Santa Croce, but with neo-Renaissance forms which houses some precious sacred works of art.

Greve also offers the opportunity to taste many typical Chianti products. In fact, under the arcades of the square, there are many artisan shops, wine bars, and restaurants, where you can dedicate yourself to tasting food and wines.


Montefioralle, Chianti

Montefioralle is a characteristic medieval village located in the municipal area of ​​Greve in Chianti from which it is just over a kilometer away. It is a real gem ideal for a nice relaxing walk. Among the buildings of Montefioralle, we recommend the church of Santo Stefano and the house of Amerigo Vespucci; near Montefioralle, the beautiful parish church of San Cresci is also worth a visit.


Panzano, Chianti

Panzano is another beautiful Chianti town which, since the 12th century, has played an important role in defending the territories of Florence. The Castle of Panzano was in fact an important bulwark in defense of the Republic of Florence in the wars between Florence and Siena. Traces of the castle remain evident in the ancient town, dominated today by the Church of S. Maria, dating back to 1200, but completely rebuilt in 1800 according to the neoclassical style.

It is pleasant to walk around the ancient town and breathe the air of times gone by and linger in the main square to have a glass of wine. In fact, in Panzano, there are some wine bars and restaurants offering wine tastings and typical products.

Nearby is the Pieve di San Leolino, dating back to 982. Despite the Renaissance aspect of the exterior, the parish remains a splendid example of a Romanesque basilica with three naves. Inside there are some precious works of art by local masters.

Castellina in Chianti

Castellina in Chianti

Castellina in Chianti is a pretty town of Etruscan origin born on a hill overlooking the surrounding valleys, full of souvenir shops and sales points of the wineries in the area. Its favorable position made this town an important strategic and military capital between Florence and Siena. The imposing fortress that dominates the central square and the suggestive walkway of Via delle Volte that crosses the town and offers glimpses of the breathtaking panorama remains today. Walking through the city you can also admire beautiful stately buildings that belonged to important Sienese and Florentine families.

Also worth seeing is the Church of S. Salvatore rebuilt after the Second World War but which houses a beautiful fourteenth-century fresco inside. Definitely worth a visit is also the Archaeological Museum of Chianti, which traces the ancient history of this area and preserves many Etruscan finds.

Radda in Chianti

Radda in Chianti

Continuing the tour we reach Radda in Chianti which still retains its original medieval appearance. The ancient walls still protect the town center, which develops in a maze of concentric alleys. The Palazzo del Podestà dominates the centre, together with the Church of S. Niccolò of Romanesque origin. On the outskirts of the town there is also the ancient Franciscan Convent of S. Maria in Prato.

Castello di Volpaia

castello di Volpaia, Chianti

Near Radda is the Castello di Volpaia, an ancient fortified village. The stone construction has a characteristic dark color, which makes the castle different from other Chianti fortifications. Despite having been damaged during the wars between Florence and Siena, the structure is still clearly recognizable with the mighty main tower and one of the smaller towers. Also worth seeing is the Commenda di S. Eufrosino, a fifteenth-century church now deconsecrated and home to a wine shop. Today the Castello di Volpaia is a small tourist village where you can taste excellent wine.

Gaiole in Chianti

Castello di Brolio

Gaiole in Chianti, whose origins date back to the Middle Ages, due to its position halfway between Chianti and Valdarno it had become an important market place for the various surrounding castles. Even today Gaiole plays an important role in the area, as it is a town of great tourist attraction. In fact, here many farmhouses and wine bars offer their products and their hospitality.

Around Gaiole, there are some castles and fortified rocks that deserve a visit such as the Badia di Coltibuono, the Castello di Meleto, the Pieve di Spaltenna or the Castello di Brolio today residences for your stays in Chianti and to taste their products.

Castello di Brolio is an imposing pentagonal fortified building. The wall walkway and the splendid gardens make it an evocative place. The castle, owned by the Ricasoli family for several centuries, is the seat of one of the main Chianti wineries; during the visit, you can also have a wine tasting.

Born around the year 1000 as a Benedictine monastery, Badia di Coltibuono was transformed into a villa-farm in the early 19th century. The abbey enjoys a beautiful location surrounded by lush forests and is today the heart of a winery whose products can be tasted during the visit.

Castelnuovo Berardenga

Castelnuovo Berardenga, Chianti

We then continue to Castelnuovo Berardenga, founded in 1366. In Piazza Petrilli, we can still see the remains of the high tower, transformed in 1755 into the town’s clock tower. The square offers a large open space where you can enjoy the atmosphere of other times; together with Vicolo dell’Arco and its characteristic red brick arches, it represents one of the places to stop and admire what surrounds us in this beautiful town in the Chianti area.

San gusmé

San gusmé, Tuscany, Italy

Just outside the town, there is the enchanting San Gusmé, a small and characteristic village that seems to have stood still over time and offers many wonderful views. Nearby is the Certosa di Pontignano, a beautiful monastery where events are organized. Finally, do not forget to add Pieve Pacina to your itinerary, less than 3 km from the town center, perhaps one of the oldest churches in the area.

Nearby there is also Villa Chigi Saracini, built in the 19th century and surrounded by a beautiful Italian Renaissance garden and an English-style park.



The last town on our itinerary in Chianti is Monteriggioni which can be reached by taking the last stretch of the Chiantigiana road. Even today the urban profile is characterized by medieval walls, among the best preserved in Tuscany. The town, a stop on the ancient Via Francigena, extends above a low hill with the central square, churches and ancient streets.



Before arriving at Siena,  is worth a visit Pievasciata, a contemporary art village, where art and nature come together in curious sculptures, which meet in the streets of the town and along the access roads. In an oak forest, 25 internationally renowned artists have created as many contemporary art sculptures perfectly inserted in the environment, giving life to the Chianti Sculpture Park. Each work was created after the artist visited the place: this makes strongest the bond with the surrounding environment, plants, light, colors, and every other element of nature. Furthermore, many works are interactive.

Wine and food in Chianti

Chianti Classico is one of the noblest wines in the world and boasts the name of the land from which it borns, in compliance with strict rules that protect and guarantee its quality. Chianti Classico must be aged for at least 11 months (it can only be drunk starting from the year following the harvest) and have a minimum alcohol content of 12 °. The undisputed protagonist of the Chianti Classico is the superior quality Sangiovese grape, present in percentages that can range from 80 to 100%.

Chianti is therefore the maximum expression of good food and typical Tuscan products. The hills here are rich in vineyards and olive groves, but not only oil and wine are made in the Chianti region: meats, cheeses, bread, typical dishes and the best of the Tuscan tradition are found in all the restaurants and in the agritourism where the products reach the table directly from the field.

Getting around in Chianti

Today the expression “Chianti” means the territory of the municipalities of Castellina in Chianti, Gaiole in Chianti, Greve in Chianti, Radda in Chianti, and in part those of Barberino, Tavarnelle, Castelnuovo Berardenga, Poggibonsi and San Casciano in Val di Pesa.

All the places in Chianti can be reached by car, motorbike and public transport from the main Tuscan cities. Although in Tuscany the railway network is well developed, there are no trains that reach the main towns of Chianti, except Poggibonsi and Castellina in Chianti. By bus, you can reach almost all the places in Chianti, but the only difficulty is the times and the not very frequent rides.

The car is therefore certainly the best alternative if you want to freely explore the Chianti area. Besides all, the “Via Chiantigiana SR222” is one of the most beautiful roads in Italy. Cross the whole Chianti area from Florence to Siena, and following this route is a good way to discover its territory.

For lovers of sports and outdoor activities, Chianti is also the right place to devote himself to cycling, hiking, or horseback riding.

Best time to visit Chianti

Every season is good for visiting Chianti. Spring and autumn are the best times, those in which the landscape and climate are pleasant and the low season allows you to find less turnout and more advantageous prices. The countryside blooms and gives all its beauty. In summer Chianti is the right place to relax and find milder temperatures. In this season and until autumn all the villages and towns come alive with festivals and events linked to the traditions, history and culture of wine and good food.