Top Things to See in the Chianti region of Italy
cosa vedere nel chianti

If you are a wine and green landscape lover, come to the Chianti region of Italy! You will rediscover the pleasure of relaxing in nature and enjoying good wine.


In the heart of Tuscany, there is one of the most popular areas of the region: Chianti!

Located between Florence and Siena and between Arezzo and the Pisan Hills, it is characterised by unique landscapes, with gentle hills, wide expanses of vineyards and olive groves, villages, fortresses, characteristic parish churches and stone farmhouses. The landscapes are so beautiful that they are often reproduced on postcards and calendars!

As many people know, the name of the Chianti region has been linked to that of the famous DOCG wine since 1984, as it is one of the best known Italian wines in the world.

Because of its beauty as well as its food and wine, this area is a popular destination for many travellers, both Italian and foreign, so much so that the English have nicknamed it Chiantishire, or Chianti County. They have moved here to live or spend their holidays, such as the English singer Sting, who bought an estate here called Tenuta il Palagio.

This land is perfect for every need: it is wonderful for those looking for a romantic weekend or for those who want to spend more time in the area, discovering the relaxation, culture, food and wine that it hides.

So, no more talking, find out with me all the best things to see in Chianti, let’s go!!! 😉


🧳 Want to explore Chianti? See all the experiences!


Visiting the Chianti region

The Chianti hills comprise an area of 20 km, including the provinces of Siena, Florence and a small part of Arezzo. Valdichiana and Valdarno mark the border of the Chianti region, to the west it extends to the Pisan hills, to the north to the Pistoian hills, to the east to the hills of Arezzo, and to the south to the hills of Siena. The highest mountain is San Michele at 893 metres above sea level, in the municipality of Greve in Chianti in the province of Florence.

The grape varieties cultivated in this area are those called Chianti DOCG, although it must be said that the borders have always been disputed. The municipalities of Radda, Castellina and Gaiole are historically considered the oldest in Chianti. In fact, in the past they were part of the League of Chianti, represented by the famous Black Rooster, while today the expression Chianti refers to the territories of the three municipalities in the League, San Casciano and Tavernelle in Val di Pesa, Greve in Chianti and part of Barberino in Val d’Elsa, and the Sienese municipalities of Castelnuovo Berardenga and Poggibonsi.


The legend of the Black Rooster

Behind the figure of the Black Rooster, that we find on every bottle of Chianti, there is a legend that will surely make you smile.

It is said that at the time of the medieval struggles between Florence and Siena, who had always contended this territory, tired of bloody fights, they entrusted the resolution of their problems to a challenge between two knights. The border between the Florentines and the Sienese would be established at the point where the two knights would meet, each leaving his own city at dawn…

It was therefore a test of speed: the one who ran faster would win more ground! So, to mark the arrival of dawn, the Sienese chose a white cockerel that they stuffed with food, waiting for it to crow louder in the morning. The Florentines chose a black cockerel which they starved to death and which, bitten by hunger, crowed much earlier in the morning than the Sienese cockerel. The latter, instead, numb from food, gave the go-ahead to the horseman much later.

The challenge ended with the border being set just 12 km from the Sienese walls and the Republic of Florence being able to annex the whole of Chianti region.


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Chianti Subzones

In order to talk about the Chianti subzones, it is necessary to clarify the word “subzone” in this context. It is a term used to indicate a smaller geographical area located within the wine appellation, where wines of higher quality than the average of the rest of the territory are often produced.

Once we have clarified this, we can move on! Today there are seven subzones in Chianti, without taking into account the “Chianti Classico” wine appellation, which has obtained an autonomous regulation. Let’s see what they are, starting with the history of Chianti Classico.

  1. In 1996 the Chianti Classico wine appellation was separated from the other subzones by an autonomous specification. The specification granted the wine from the oldest Chianti area of origin (i.e. located between the cities of Siena and Florence, including the entire territories of the municipalities of Greve in Chianti, Castellina, Gaiole, Radda, as well as part of the territories of Barberino Val d’Elsa, San Casciano in Val di Pesa, Tavarnelle Val di Pesa, Castelnuovo Berardenga, Poggibonsi) the right to use the word “Classico”.
  2. Chianti Colli Aretini, in the province of Arezzo
  3. Chianti Colli Fiorentini, in the province of Florence
  4. Chianti Colline Pisane, in the province of Pisa
  5. Chianti Montalbano, produced between the provinces of Pistoia, Prato and Florence
  6. Chianti Rufina, the smallest subzone of all, situated in the province of Florence, in the municipality of Rufina and adjacent areas
  7. Chianti Colli Senesi, in the province of Siena
  8. Chianti Montespertoli, the latest addition, in the territory of Montespertoli


The best things to do in Chianti Italy

Follow me here to find out what to see in the Chianti region! I will first explain the best things to see in Chianti Classico, and then go on to explore other areas. This tour will include charming villages, magical itineraries related to nature, sports, food and wine.

In particular, if you are passing through Chianti, a great way to experience the area is to drive along the “SR 222 Chiantigiana” which connects Florence to Siena. It is a must to admire the beauty of the landscapes and villages… Also perfect by bike or Vespa!

So let’s get going! 👇


What to see in Chianti?


1. Greve in Chianti

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This is the only municipality in the province of Florence to fall entirely within the Chianti region. It is a truly evocative place, which I recommend you visit!

The heart of the town is Piazza Matteotti, with its unusual triangular shape, surrounded by arched loggias, shops and taverns to immerse yourself in the local traditions. In the centre of the square stands the statue of Giovanni da Verrazzano, the famous explorer who was born here in Greve and discovered the bay of present-day New York and most of the east coast of the United States. In fact, New York has a famous bridge, suspended between Brooklyn and Staten Island, named after him in 1964. Back in Greve, however, we find the Castello da Verrazzano, where Giovanni was born.

The church of Santa Croce also stands in the square and contains important works of art, including a triptych by Bicci di Lorenzo depicting the Madonna and Child with Saints. In addition, the Wine Museum illustrates the history of Chianti DOCG, which has always been produced in this area.


2. Montefioralle

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Montefioralle is a small town just above Greve in Chianti. It originated from the fortress, around which the houses and town streets were built, as well as the church. Around the houses there is an elliptical fortification, very well preserved.

The traditional local foods, apart from Chianti Classico of course, are the artisan cold cuts and the famous Florentine steak, served with the classic white beans, as well as the cantucci biscuits and local Vin Santo.

A special event in the area is the “Festa delle Frittelle” in March, when pancakes that housewives used to cook in country houses are served in a small square. A fun experience that should be included in the list of top things to do in Chianti.


3. Radda in Chianti

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It is the most charming town in the Chianti Senese area. The town attracts visitors with a series of patrician palaces, the result of the renovation of former military garrisons. The Etruscans also passed through this town, with evidence such as the “Tumulo di Montecalvario”, consisting of four tombs arranged on the four cardinal points. Worthy of note is the Pieve di Sant’Agnese in Chianti, located in the nature reserve of the same name, which was partially destroyed during World War II. Today the base of the mighty bell tower, once a defence tower, remains.

The typical foods of the place are, for example, Chianti DOCG, Chianti Classico olive oil PDO, ribollita or tripe.

Absolutely not to be missed is the Sienese Chianti Archaeological Museum, which tells the story of Chianti through archaeological materials and data collected in the four municipalities on the Sienese side: Castellina, Gaiole, Radda and Castelnuovo Berardenga.

Radda certainly answers perfectly to the question: what to see in Sienese Chianti?


4. Gaiole in Chianti

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Flickr, Drew Reese – Gaiole


Surrounded by steep hills and narrow valleys, the area is mainly made up of forests with oak trees, vineyards and olive groves. Gaiole in Chianti has always played an important role as a “market town” for neighbouring towns. It has got a triangular-shaped square, where many cultural events related to the wine tradition are organised. Here you will find a beautiful Romanesque church called Pieve di Spaltenna: an enchanting place that is definitely worth a visit! We also find the Brolio castle near Gaiole, which represented a powerful and strong defensive point, thanks to its position with a strategic view over Siena.

Finally, Vertine is a fortified village visited by a considerable number of tourists every year.


5. Castelnuovo Berardenga

It characterises the southern part of the Chianti region and is a wonderful place to spend a day in unspoilt nature. For those interested in history and culture, there are also several churches to visit, dating back to the 17th century.

A hamlet of Castelnuovo is San Gusmè, a fortified village with a circular shape, enclosed by walls, which still exist in part. A special feature of San Gusmè is the statue dedicated to Luca Cava, which is intended to show people where to collect fertiliser for the gardens.


6. Barberino Val d’Elsa

Barberino Val Elsa is a fortified village located halfway between Florence and Siena, in the northwestern part of the Chianti region. Thanks to its position along an important communication route, it became one of the main centres of the Florentine countryside.


7. Tavarnelle Val di Pesa

A hamlet of Barberino Tavarnelle, its territory is partially included in the Chianti Classico area and partially in the Colli Fiorentini sub-area. Its land is entirely dedicated to agriculture and viticulture, the strong foundations of its economy. Worth visiting here is the Pieve di San Pietro in Bossolo, a Romanesque church with Roman and Byzantine works.


8. San Casciano

Coming from the north, this is the first Chianti municipality you come across. It is a territory characterised by small hamlets, parish churches and hamlets to explore. In the village, you can admire the remains of the city walls and medieval towers.

Incidentally, Niccolò Macchiavelli lived here in San Casciano! He took refuge in the “Casa di Sant’Andrea in Percussina” after being exiled from Florence in 1512.


9. San Gimignano

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Known for its towers that stand out against the horizon, it is one of Tuscany’s most popular destinations. It was declared a UNESCO World Heritage Site in 1990 and is known as the “Manhattan of the Middle Ages” precisely because of its number of ancient towers. In fact, in its heyday there were 72 towers, while today there are 13.

10. Volterra



Volterra is a village built on a small hill between the Era and Cecina valleys. It has double walls, one Etruscan and one 13th century, and it is these elements that give it its much-appreciated medieval appearance.

The village was one of the main city-states of ancient Etruria and was also the seat of an important bishopric.

Volterra is also famous for its alabaster, one of the most important Italian handicrafts, which is certainly one of the things to see in Chianti! It is also rich in art, which can be admired by walking through the streets of the historic centre and visiting the town’s museums, such as the Etruscan Museum, the Art Gallery and the Museum of Sacred Art. In March Volterra hosts the Marzuolo Truffle Market Fair with all traditional foods of the Alta Val di Cecina, while in October Volterragusto returns every year with its events dedicated to truffle and more.


11. Monteriggioni

Even in this wonderful village we find a wall that embraces the entire town. It was built for defensive purposes as it has a strategic position to control the Valdelsa territory. It also has fourteen imposing towers, which stand out against the sky.

The point of greatest interest is the Castle of Monteriggioni, founded in 200 by the Republic of Siena.


12. Siena



It is a very famous city in Tuscany, showing itself today as it did in the 14th century and with a unique medieval architectural heritage. The city’s attractions are many, here are some of them:

  • The Town Hall
  • The Mangia Tower
  • Piazza del Campo
  • The Cathedral

As many people know, the city is famous for the Palio di Siena, which is held here twice a year as a traditional custom. It consists of a horse race contested in Piazza del Campo by the city’s contrade. Definitely a unique experience to be had in the Chianti region!

In December, the same square hosts the Mercato del Campo, while the Santa Maria della Scala complex (one of the first hospitals in Europe) organises many exhibitions worthy of a visit.

For those planning a multi-day holiday, south of Siena are the exceptional views of the Val d’Orcia, a UNESCO World Heritage Site. The area is characterised by hills and gullies, but above all by cypress trees that crown the hills in isolation or follow the contours of the roads. There are also wonderful villages to visit!


What to do in Chianti?

I can assure you that there are plenty of things to see in Chianti, but there are also many activities that will surely make sure you never get bored.

In this wonderful region, you can organise either itineraries to discover medieval villages, historical sites (such as Etruscan or Roman). Of course you can devote yourself entirely to nature and the landscape with excursions on foot, on horseback or by bike, or go trekking. On the other hand, if you are looking for relaxation, why not organise a nice day at the spa? An activity that I highly recommend is simply to drive through the Chianti valley, following the roads offered by the beautiful hills, to admire the panorama dotted with olive groves and vineyards.

In short, you can organise your tour of Chianti however you like, according to every taste and need! Other activities could be Tuscan pottery courses or a visit to the Chianti Sculpture Park.

Finally, don’t forget that September is the grape harvest month, an activity you can’t miss when visiting the Chianti region!


Enjoy food & wine in Chianti

It is clear at this point that in Chianti food and wine are the undisputed kings, with extra virgin olive oil, typical cold cuts and cheeses, pappa al pomodoro, Florentine steak and much more. This area makes us dream!

When visiting Chianti, you can’t miss any of these delicacies! Worth mentioning is Panzano in Chianti, a village about halfway between Greve and Castellina. It is a quiet resort town, known for the old Cecchini butcher’s shop. Its owner Dario Cecchini has recreated his family butcher’s shop in the old style in a very creative way and it has become a tourist attraction. It is the ideal place to buy unusual cuts of meat of extraordinary goodness!

Other activities that include gastronomy when visiting Chianti include truffle hunting experiences in the beautiful local woods, winery tours with tastings, aperitifs with a view or full weekends at the wineries.

An interesting experience is to visit the Chianti Classico Wine and Olive Oil Route, which winds through an amazing area with olive groves, vineyards and picturesque villages to visit. This trail has existed since time immemorial and today gives those who travel along it evidence of the passage of several peoples. The latter have made the Chianti region become what it is today, one of the world’s most appreciated food and wine treasures.


When to visit Chianti in Tuscany?

I have explained the things to see and do in Chianti, but now follow me to find out when is the best time to visit the region! Chianti is suitable for all seasons, but spring and autumn are the best periods, as the climate is pleasant. In addition, being low season, you can visit it with more tranquillity, enjoying the changing nature to the fullest.

In this area there are various events: in particular, in the picturesque villages of Chianti, there are often festivals and events linked to local traditions, history, food and wine. Some of the best known events in Chianti Italy are:

  • the “Festa della stagion bona” in Panzano in Chianti, where a historical commemoration is held in March with a costume parade to propitiate the arrival of spring, food stands and street entertainment
  • the Autumn Festival in November in Greve in Chianti
  • it is impossible not to mention the grape harvest in September, which enlivens the area with joy and colours.


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Getting there and around the Chianti

Getting around by car is certainly the most comfortable and practical option, as you can admire the landscape and stop at as many wineries as you like. Bikes or scooters are also valid alternatives, while public transport is available:

  • the train: Although the railway network is well developed in Tuscany, it does not reach the main towns of Chianti. There are only two railway stations in Chianti, Poggibonsi and Castellina in Chianti, with departure and/or arrival in Florence or Siena.
  • by bus: you can get almost everywhere by bus, but be patient as they do not run at all times, so it is definitely something that needs to be organised first!

At this point my guide ends here, I hope I have explained to you as best I can all the things to see and do in the Chianti region and I encourage you to visit this wonderful area and share in its joy and purity!

All that remains is for me to wish you a pleasant journey in Tuscany! 🧳


About Author

Clara Caponetti
Ciao sono Clara! Sono laureanda in Scienze e Culture Enogastronomiche presso l’università Roma Tre. La mia passione è la cucina, adoro viaggiare e scoprire sempre nuove ricette e tradizioni, perciò non vedo l’ora di condividere tutto con voi!


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