Castellina, Radda and Gaiole


Discover the three villages of the Chianti Storico, where the iconic Chianti Classico vine is produced.
You will be surrounded by breathtaking views of rolling hills on which rise long vineyards that change color depending on the season.


Castellina, Radda and Gaiole is the triangle of the Chianti Storico, the territory of the iconic vine. Rolling hills covered entirely by vineyards are waiting for you!
Certain versions explain that the name Chianti comes from the Etruscan word Cluntni, a name imprinted on a piece of ceramic discovered in Cetamura in Chianti, probably the name of the vase’s owner. Otherwise, the name could derive from the Etruscan Clante, that means water, of which the area was and is still today very rich.
It is said that during the Middle Ages, the Republics of Siena and Florence wanted to obtain both the territory of Chianti, this was the subject of continuous struggles, precisely because it was located in the center of the two cities. To end the disputes and to establish a definitive border, it was decided to organize a race between the two cities. You will then discover the legend linked to the two roosters, the black and the white one that will explain the symbol of today’s Chianti Classico vine: il Gallo Nero (the black rooster).
Chianti is therefore a border land between Siena and Florence, the territory of the Chianti League was established, where many fortifications were built. In 1163 the precise borders of Siena and Florence were established for the first time.
You will start the tour in Castellina in Chianti, whose origins date back to the Etruscan times, as attested by the mound of Monte Calvario. The archeological finds can be explored in its Archaeological Museum. Castellina is situated in a strategic position, on the ancient road that leads to Siena, and so it was the most advanced point of the Florentine municipality in the direction of the rival city Siena.
The tour continues towards Radda, which rises in the heart of the Chianti mountains. The Palazzo Pretorio of the 15th century became the seat of residence of the Podestà, the most important political figure who represented the Florentine Republic. On the facade of the palace in fact you will see the coats of arms in stone and terracotta of the many Podestà who governed the city over the centuries.
The visit will end in the last village of Chianti, Gaiole, like the other two it is located on the highest point of the mountain.
Castellina, Radda and Gaiole are surrounded by breathtaking landscapes, vineyards, woods, hills and unique trees.
The production of Chianti Classico vine unites these places. You will discover the history linked to this famous DOCG vine, a denomination of controlled and guaranteed origin, the highest recognition for quality Italian vines.
On request, we can organize a Chianti Classico vine tasting in one of the beautiful vineries located in the area.


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Giulia Vannini

My name is Giulia. I am a hiking and diving guide. My passion for nature and animals has accompanied me since I was a child in all my studies. I graduated in Biology and then specialized in Marine Biology, I studied around Italy in important universities and research laboratories. After the Master in Environmental Legislation I returned to my beloved Siena, where my family and my dear friends were waiting for me.
I am from the Shell neighborhood (Contrada del Nicchio), you will discover in our company that the “Contrada life” in Siena is very important since childhood, and it is one of the things that makes this city unique!
Since I was a child I had a passion for teaching, over the years I worked in schools as an educator and so I developed interesting projects in the field of environmental education. My passion for playing with children will never end and in fact I am also a swimming instructor, specialized for people with psychophysical problems.

Thanks to Siena Tourism I create tours and events combining all my studies and my passions. We thought of many walks to do, alone or with the whole family, and many beautiful activities dedicated to children! I expect you soon to discover our enchanting territory together!

Ludovica Noviello

My name is Ludovica and I was born in Rome, where I attended the German school. After the diploma I studied at the Humboldt University in Berlin at the faculty of Foreign Languages and Literature. For many years I lived around Europe, where I worked and continued to study languages. My passions are art and foreign languages, so I decided to move back to my beautiful country to combine them in my job as a tour guide. I moved to Siena, where I studied to become a licensed Tour Guide in Italian, English, German, French, Italian and Spanish.
Siena is an enchanting city, a treasure chest that holds many artistic and cultural beauties and my job is to transmit my love for Siena and the many villages in the Province to those who come to visit it.
As a member of Siena Tourism I am also one of the organizers of this great project.
Our aim is to make you know the best of some of the cities and villages in Tuscany, offering you many beautiful moments to remember forever.
I am sure that this part of Italy will find a special place in your heart!