Chianti in Tuscany is famous, in fact very famous, around the world for the production of wine highly appreciated by both connoisseurs and enthusiasts. The Chianti region is hilly and sometimes wooded and sometimes shaped by man, passed as a baton from one generation to another. Crossing the Chianti hills you will meet cypresses, olive trees and vines that create an unforgettable backdrop to the landscape. Besides the natural beauty there are numerous ancient churches, castles, old farms and farmhouses.
Although its main locations are divided between the three provinces of Siena, Florence and Arezzo, it is difficult to determine the borders of some of its rural areas. Each of the three provinces struggle to be recognized as the main and most prestigious area! In particular, it is common to refer to the old part of the Siena area that was under the League of Chianti (with the symbol of the famous black rooster on the golden background), where the towns of Gaiole in Chianti, Radda in Chianti, Italy and Castellina in Chianti, Italy can be found. This division dates back to the Middle Ages: with the passing of the ages and the expansion of crops other locations were added in the so called sub-area of Chianti, Tuscany including the well-known Greve in Chianti which is located in the province of Florence. If you are in Florence it could be easier to reach this area with a day trip to Chianti especially for you!
The most famous wine is Chianti Classico, also called Gallo Nero, which is protected by the Consortium of Chianti Classico. This fantastic wine is produced primarily from Sangiovese grapes, and sometimes with small percentages of Italian grape varieties like Canaiolo or international grapes such as Merlot. The Chianti DOCG wine is checked at every stage with the utmost care making it famous throughout the world for its high quality. A taste of the Chianti Classic will reveal its unique characteristics such as its ruby red colour, fragrant floral notes and the dry and savoury flavour. You can try, in addition to the so-called Young, a Chianti Classico Riserva with a more velvety and darker colour. Please note that Chianti starts from a minimum alcohol percentage of 12 degrees, so it is best not to drink it on an empty stomach! Combine your goblet with a Tuscan crostini, a Florentine steak or pecorino cheese cake!
In the valley of Chiant itinerary you will see, in the summer (especially in September), the vines full of ripe grapes with a purple shiny colour. You will be dying to try them, but they are only destined for the barrels! Be enchanted by the phases of production and discover the most important wineries of the Chianti area with a private tour of Siena and Chianti from Florence that meets your curiosity and your palate!
Tuscany Chianti is the most picturesque and characteristic area that is loved and appreciated abroad; especially by the British, who love the mild climate and the beauty of the area; they have even jokingly renamed it Chiantishire (county of Chianti). The beauty of these places will not leave you untouched! It is also said that Da Vinci came to Chianti to paint Mona Lisa...
In your Chianti wine trail we suggest you first visit the main areas of the ancient 14th century military league and some lesser-known destinations in the sub-area. It is not easy to choose between many small towns and villages!
If time is short, do not despair, we can offer day trips to Siena and Chianti from Florence that will allow you to visit the Chianti and its wineries without any stress or problems!
Here are some places not to miss:
CASTELLINA IN CHIANTI, ITALY (SIENA). This city, once Florentine, represented a strategic bulwark in the Middle Ages due to its elevated position connecting the two powers of Tuscany. When you arrive we suggest, that the first thing to do, is to visit the Archaeological Museum of Chianti inside the fortress in the centre of the town. In the museum you will have the opportunity to learn about the origins of the Chianti area and its productions. If you want to enjoy the view, you can climb the tower of the Rock or take a walk along Via delle Volte, or the covered walkways of the old walls. In the old town you will find many craft shops, shops, taverns and especially the Antiquaria Wine Tavern, located in the historic Palazzo Squarcialupi, and if you look for the characteristics of a Chianti docg or the differences between a young Chianti Classico and Chianti Riserva you are in the right place!
RADDA IN CHIANTI (SIENA), ITALY. Among the hills of Chianti is another beautiful medieval town surrounded by walls. Radda in Chianti is a perfect place to relax, shop and stroll through its narrow streets. This town, whose origins date back more than a thousand years, became the administrative headquarters of the League of Chianti from the 14th century onwards. Like other villages in this area, it is located in an elevated position and therefore strategic for the Middle Ages; its old town is dotted with Romanesque churches including the churches of St. Nicholas and Santa Maria Novella. Two other interesting elements of this town are the 19th-century Grand Duke's Ice Room (used to preserve the snow) and the Museum of Sacred Art of Chianti located in the rooms of the Convent of Santa Maria in Prato. After visiting the town we advise you to visit the village of Volpaia, famous for its castle, the Renaissance church of the Commandery of San'Eufrosino and for the production of Chianti Classico (Volpaia Farm). If you have time visit some of the historic wine cellars and stop for some tastings!
GREVE IN CHIANTI, TUSCANY (FLORENCE). Here in the Chianti wine region, Italy between Florence and Siena, is the town considered the door of the Chianti. Greve looks like a small town famous for its food and craft shops (Old Falorni Butcher’s) and a Wine Museum for those who wish to learn the origins of the wineries surrounding Florence. In the Chianti region things to see in Greve include the Rectory of St. Cross, the main church of the town, characterized by a neo-Renaissance facade and, inside, the works of Bicci di Lorenzo (Madonna and Saints) and Santi Buglioni (Ciborio terracotta).
Not far from here is Montefioralle, one of the oldest villages in Tuscany. The Chianti Classico is waiting for you here within its walls and cellars at your disposal! Curiosity claims that this village was owned by the family of Giocondo, i.e. the famous Mona Lisa painted by Leonardo! To reach Greve you can choose a private tour in Chianti from Florence full of surprises!
GAIOLE IN CHIANTI (SIENA). This town near Siena is in close contact with the area of Valdarno and thanks to this closeness it was often a place of trade between the various castles. The centre of Gaiole was part of the ancient Chianti League, from the fourteenth century, as a centre of the sales activities of villages and houses of lords. Unlike other towns in Chianti which look like fortresses surrounded by walls, Gaiole was a city of passage for those who had to do business with the exchange of goods and sales of raw materials. Once you have seen the old town, we suggest you discover the strongholds surrounding this ancient village.
In particular, the Brolio Castle is one of the most beautiful castles in the Chianti area of Siena. This imposing castle, of Lombard origins, has been owned by the illustrious Florentine Ricasoli family since 1141. Its proximity to Florence, its location and its lonely massive structure meant that it was often a source of contention between Siena and Florence, with numerous sieges and looting. The castle, then, was rebuilt after its destruction and major changes have since occurred in the 19th century. Baron Bettino Ricasoli changed its original neo-Gothic castle and made it more like a romantic English castle. This figure, also known by the nickname Iron Baron, is most famous for his passion for Chianti wine (he also invented the modern wine-making) and for some legends that say that his ghost still wanders the halls of the castle! Visit (without fear!) the Crypt of the family and the Museum of the Ricasoli family: discover more information about this family and its role in the world for the export of Chianti wines. Brolio will charm you with its history and also to the memory (perhaps) of the scenes of the film by Bertolucci "Stealing Beauty": this location is definitely worth a visit!
If you are interested in visiting a farm and to discover its fantastic products write down, on your map of Chianti, the Badia in Coltibuono. This place, which was once an abbey, was transformed into a villa in the 19th century and it is now a of wine and oil company!
CAVRIGLIA (AREZZO). During your holiday in Chianti, you should go and visit Arezzo to find a very special and rare place. The Cavriglia rose garden, in fact houses species from around the world. The Roseto Botanico Carla Fineschi Casalone boasts the great work of Professor Fineschi: seven hundred varieties, some of which are endangered, make this collection one of the most important rose gardens in the world. You'll be surprised by this garden, enchanted by the different colours and countless species of one of the most romantic and symbolic flowers ever. The view of this garden is completed only with the olfactory experience of the different fragrant and delicate roses, that undoubtedly will conquer you! After the visit you should learn about the Chianti Colli Aretini wine...
CASTELNUOVO BERARDENGA (SIENA). This town is located on the hills from which Chianti Colli Senesi and Chianti Classico orginate and is one of the best places in Chianti. Before you think about wine, explore this city of medieval origins, that belonged to Siena since the days of the Republic, and was the subject of contention between Siena and Arezzo for a long time. Do not miss the Alley of the Arch in the main square and the Church of San Giusto and Clemente in neoclassical style, a rarity in these areas characterized by the medieval legacy. Taking this village as a starting stage you will find interesting destinations nearby. We at toscanainside.com recommend a visit to the Chianti Sculpture Park which is located in Pieveasciata, in the town of Castelnuovo. It is an open air museum that was created in the early years of the millennium thanks to the work of Piero and Rosalba Giadrossi. In a path between oaks and trees of various kinds you will encounter installations, statues and works of contemporary art. Depending on the season, the sculptures take different shapes and shades capturing the natural light and giving you a unique experience full of art and nature hard to find elsewhere. If so desired, you can also explore the park by bike!
Historical curiosity: along this scenic road in Chianti is the town of Montaperti, does this remind you of something? On 4 September 1260 this area was the scene of the terrible Battle of Montaperti fought between the Ghibellines of Siena and the Guelphs of Florence. The victory was in favour of the Sienese army and Dante in the Divine Comedy meets one of the Florentine exiles heading the Ghibellines: Farinata degli Uberti. In the talks with this soul from hell, the poet recalls the horror of the battle in which the river Arbia was reddened by the blood of fallen soldiers.
For the size and the numerous villages of Chianti in Tuscany, Italy we recommend you have a reference map to avoid getting lost in the countryside. The same holds true for Chianti wines. For non-experts it can be difficult to navigate between the different vintages and different productions: in addition to the Chianti Classico you will be faced with a world of choice. During your visits to wineries you can taste a Chianti Rufina or a Chianti Colli Arezzo, a Chianti Colli Senesi or a Chianti Colli Fiorentini. Our suggestion is to discover the cellars from time to time, in stages, to give your palate the chance to enter each time in contact with different culinary experiences and so as to make the trip a magical encounter between land, art and wine tradition.
Choose the Chianti from Florence tour that interests you most: these are the holidays to discover Chianti!
Need help choosing
Tours & Activities
Day trip to Siena, San Gimignano and the Chianti area
Duration: approx. 11 hours
- Per person
- € 57.00
Tours & Activities
Chianti wine tour from Florence
Duration: approx. 5 hours
- Per person
- € 45.00
Tours & Activities
Guided tour of Siena with a short course in ice cream making
Duration: approx. 1 hour and 30 min.
- Per person
- € 42.00