Private Chianti tour

chianti private tour
  • Badia a Coltibuono

  • Hamlet of Vertine

  • Radda in Chianti

  • Governors Palace in Radda

  • Castellina in Chianti

  • Castellina in Chianti Castle

Tour duration: 2/4/6 hours
Difficulty: low
Suitable for children: yes
Differently abled accessibility: no
Difference in level: 30 metres



Further information at the bottom of the page (or click here)

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.

chianti private tour


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

tour castelli chianti

Archeological Museum, Castellina in Chianti

Picturesque Alley, Radda in Chianti

Important information about the tour (click here)

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

The activity here proposed is a private and not a joinable tour; this means that it is a tour only carried out on request and can be customised for starting time, meeting place and duration, depending on the customer’s needs.



Duration of Chianti private tour

The duration of the Chianti tour can be 2.4 hours or 6 hours. With the 2-hour visit we can visit Gaiole in Chianti, Badia a Coltibuono and Vertine. With the 4-hour visit we can visit Gaiole, Badia a Coltibuono, Vertine and Radda in Chianti. With the 6-hour visit we visit Gaiole, Badia a Coltibuono, Vertine, Radda in Chianti and Castellina in Chianti.

Organise break for lunch

The eventual stop at a farm, winery or restaurant is not included in the cost of the tour since it is an external service. Likewise, the guide can suggest to the clients places where they can take a break to eat but, not being a tourist agency, the guide cannot offer the reservation service for meals or tastings. Therefore, the break for lunch or the tasting of typical products continues to be ordered directly by the client.



Radio rental compulsory from 6 people onwards

From 6 people onwards, to facilitate listening to the guide explanations and ensuring social distancing outdoors and indoors, it is strictly recommended to rent radio devices with transmitters that ensure perfect listening to the explanations of the guide even from a distance; if you then visit the inside of the monuments, the rental of radios is compulsory for 4 or more people. The service is booked by the guide when the guided tour is requested, but the rental cost, which is € 1.00 per person for 2 or 3 hours, is charged to the customer and can be paid directly to the guide who will then take care to pay the supplier.

Carers or teachers of school groups do not pay for the rental of the radio.


Opening Hours Archeological Museum Castellina in Chianti:

April – May10:00am – 6:00pm
September – October10:00am – 6:00pm
June, Luly August11:00am – 6:00pm

Open every day


January – MarchClosed
Open in the holidaysEaster Monday, May 1st, June 2nd, August 15th, November 1st



Ticket price Archeological Museum Castellina in Chianti:

Full5,00 €



 3,00 €
Reduced ticket for groups 
15 o more people2,00 €
Reduced for scholar groups1,00 €


Free admission

Children 0-6 years old, persons with certified disabilities, tourist guides with ID cards, ICOM card holders, MiC employees, accompanying persons of school groups and groups, pupils of schools of all levels and levels of the Sienese Chianti municipalities (Castellina in Chianti, Gaiole in Chianti , Radda in Chianti, Castelnuovo Berardenga) and Monteriggioni, residing in the municipalities of the Sienese Chianti. 


The cost of the entrance ticket to the Archaeological Museum of Castellina in Chianti is not included in the tour rate



Orari di apertura Badia a Coltibuono:

Since the opening hours depended on the availability of a volunteer who opens the church, please contact the guide in advance to check the opening 

Open every day9:00am – 7:00 pm




The guide does not provide transportation service.

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 by Whatsapp o Telegram


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Cost and reservation of the tour (click here)


Cost of the Chianti private guided tour

The cost for a 2-hour private guided tour is € 120.00 (price in total and not per person), for 4 hours € 210.00, for 6 hours € 280.00 (always price in total and not per person). 

For further information about the rates, also to check the deals available, please visit the dedicated section by clicking here.

How to book the tour?

The tour can be booked by writing an email, calling at +393332591526 or texting the guide (also via Whatsapp or Telegram) to check availability for the requested day. 

Once the day and time of the tour have been agreed with the guide, to book it is necessary to advance 50% of the tour value with a deposit to be paid by credit card.

Attention: pay the deposit only after agreed the date and the details of the tour with the guide. The remaining payment of the guided tour takes place after the tour by card, in cash or by bank transfer.

Cancellation Policy

It is the responsibility of the guide to guarantee the guide service in any case. If, even for personal reasons, the guide is unable to perform the service in the date set with the client, it will be his concern to contact a trusted colleague who can replace him and therefore guarantee the customer service.

The cancellation of the tour from the client can be done free of charge by giving timely notice to the guide before 48 hours from the date and time agreed for the service. In this case the deposit paid in advance by the customer will be returned by the guide. If instead cancellation is made by the customer when there are less than 48 hours before the date agreed for the service, the customer will lose the deposit paid.

Cancellation can be made by promptly communicating it to the guide with via email, calling the number +393332591526 or by texting (also via Whatsapp or Telegram).


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How to reach Chianti? (click here)

By Car

On account of the lack of public transport connections between the stages of the itinerary, making the journey with your own car or a rented car (or with a tourist bus for a group organized with an agency) is still the most convenient way to do the entire itinerary.

Badia a Coltibuono can be reached via the A1 motorway (Valdarno exit if you are coming from Rome or Milan; then continue following the signs to Terranuova Bracciolini, then to Badia a Coltibuono.

To reach Castellina in Chianti, exit at Bettolle Valdichiana, continue for Siena and exit at Badesse in the direction of Florence, then take the SR222 for Castellina in Chianti. If you are coming from Florence, exit at Badesse towards Siena and continue with the SR 222

Free parking spaces are available in Badia a Coltibuono in the adjacent square of the abbey.

In Vertine there is a free parking area outside the village. In Radda in Chianti a free parking area along Via XX Settembre, near the cementery and along Viale Matteotti.

In Castellina in Chianti free parking is available near Viale della Rimembranza and on the north side of the old walls. Paid parking spaces are available in Via IV Novembre and in the square when you leave the SR 222. 


By train

The closest rail stations to the itinerary are Florence SMN and Siena. From these, the most convenient way to proceed is by rental car. The train timetable for Siena and Florence is available on the website of Trenitalia service.

From there the most convenient way to reach the Chianti itinerary stages is, besides a rented car:

By Taxi service

Available with positions in front of the train station or contactable at the number +39057749222, sending a message at the number +393483892305 indicating:

  • Address (Street o Square, Civic Number and Municipality);
  • Particular requests(dog or cat, payment by card, driver’s language, number of passengers if over 4, luggage if large).
    Wait for the confirmation message with the code of the arriving taxi and the estimated time


Organised groups/squadrons by tourist coach

For organised groups/squadrons by tourist coach, there are drop-off/drop-on points for passengers along the itinerary (click here to view the points). Because of the narrow streets and the few points available near Vertine, is recommended to contact the local police before to plan the tour with touristic coach


By camper van

To get more information on the Camper areas available nearby Gaiole in Chianti and Badia a Coltibuono please click here. For more information on the Camper areas near Castellina in Chianti please click here.

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