Private Chianti tour

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  • Badia a Coltibuono

  • Hamlet of di Vertine

  • Radda in Chianti

  • Governors Palace in Radda

  • Castellina in Chianti

  • Castellina in Chianti Castle

Tour duration: 6 hours
Difficulty: low
Suitable for children: yes
Differently abled accessibility: no
Difference in level: 30 metres


Further information at the bottom of the page

The Castles of Chianti, memory of a disputed land

By the Chianti private tour you will not only get to know the land where the homonymous Chianti wine is produced, which is among the most famous in the world, but you will also find yourself immersed in an area rich in history and traditions, where you can sip a glass of Classic Chianti while you will be surrounded by a truly suggestive landscape. Many people know the wine that is produced in this micro-region of Tuscany, but hardly anyone knows the beauties hidden in this territory, where the landscape is made up of dense woods alternating with fields openings with very evocative views, thousands of Sangiovese rows, very suggestive villages and, above all, an area dotted with castles and small villages. The Chianti castles are the clearest evidence of this area as a borderland, disputed in the Middle Ages by the powerful cities of Florence, Arezzo and Siena.

We begin our private Chianti tour from an ancient and very unusual abbey, a monastery that looks like as almost a fortified castle due to its imposing structures, with the mighty bell tower: Badia a Coltibuono.

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Badia a Coltibuono, the fortified abbey

Immersed in an unspoiled nature, this monastery is today a heaven of peace that hardly suggests a place of battles and aggressions, located as it was in an area of passage for travelers coming from the Valdarno markets, therefore inevitably a point affected by raids and attempts to steal the goods, which is why it needed to be defended.

We enter the church of this abbey which was a Vallombrosan foundation, inhabited by the Benedictine order founded by San Giovanni Gualberto.

Inside the church, sober in its fascinating Romanesque style, we will see the works of art that are preserved, such as a beautiful inlaid altar frontal, representing the blessed Benedetto da Coltibuono’s stories, the frescoes of the lantern, the altarpieces altar dating back to the seventeenth-century.

Visiting Vertine

Leaving Badia a Coltibuono, our second stop on the private Chianti tour is Vertine. Fortified village, dating back to the 11th century, this small town, which was born on a hill a few steps from Gaiole in Chianti, is one of the most charming rural villages in the Chianti area; cared for with truly obsessive attention by its few inhabitants, the village was an important point of control and defence of the borders in the Middle Ages and it was also an object of interest for the powerful families of the area, such as the Ricasoli-Fridolfi coterie, as still today testified by the imposing buildings in stone still preserved. The visit to Vertine is almost a temptation to escape from: when you walk through its quiet streets, your desire to abandon everything and come and live here will be strong.

After visiting this wonderful village, we take the lunch break of our private Chianti tour at a farmhouse or a winery of the area¹, this before continuing with the visit of Radda.

Castellina in Chianti

Attic amphora, 6th century BC, Archeologic Museum, Castellina in Chianti

tour castelli chianti

Radda in Chianti

Radda, the village with a black rooster as a symbol

Medieval village and administrative centre of the entire district, Radda is a place rich in evidence of its long history. In the visit I will take you to see the medieval coats of arms testifying to its important role in the Lega del Chianti (Chianti League). The thing you will certainly surprise you will be to see that as a symbol of the league there is a black rooster. Yes, the same rooster also appearing as an image on the wine bottles neck of the same name, is an animal that, as I will tell you, has a very funny story, a tale linked to the centuries-old rivalry between Florence and Siena. After having seen its monuments, our last stop on the private Chianti tour is Castellina.

Castellina in Chianti

We conclude our Chianti private tour with the visit to Castellina, a town which, despite the wounds inflicted during the Second World War, still retains that intimate character of the village where every citizen knows each other and time seems to be suspended. Crossing the tunnel designed by Filippo Brunelleschi Brunelleschi, you will feel like you are reliving the time when structures like these were strategically used to defend against enemy attacks due to the slits that are still visible here. The last stop on this itinerary is the Castellina castle. Fourteenth-century building renovated in the fifteenth century and then finally in the twentieth century, the Rocca is a significant example of a fortified structure today housing the Archaeological Museum of the Sienese Chianti, important institution that bears witness the history of the ancient settlements of the area, as evidenced by the precious archaeological finds preserved here, including painted sixth century. B.C amphorae imported from Greece and a warrior’s chariot, coming from the monumental burial of Montecalvario. The visit of the fortress ends with the panoramic view from the top of the keep.

It is hard to think that this land, today able to save visitors from the worries of a hectic daily life, was instead in the Middle Ages a land of clashes and sieges. After the private Chianti tour it may be time to taste a glass of wine, caressed by the wind blowing over these hills and contemplating the colours of the sunset.

The hamlet of Vertine

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Castellina in Chianti Castle

1: the reservation of lunch at the farmhouse or at the winery is on charge of the client, therefore this service cannot be booked by the guide who is not a tourist agency.

This tour can also be booked in combination with the other available tours on Siena and Florence, which can be consulted in the Menu.

The cost of the entrance ticket to the Archeologic Museum in the Castellina Castle is not included in the tour rate. The access to the other churches, as Badia a Coltibuono, is for free.

The guide does not provide transportation service. For organized groups/squadrons by tourist coaches, there are drop-off/drop-on points for passengers at each site on the route (click here to view the points).

To get further information, to book the tour or to get the contact of a licensed driver providing private transfer service, please write to: also on whatsapp or telegram