Hiking throughout Sienese Chianti Castles

hiking sienese chianti castles


  • Gaiole in Chianti

  • Montegrossi Tower

  • Badia a Coltibuono Monastery

  • Cetamura Archeological finds

  • Vertine Castle

  • Pieve di Spaltenna

Hiking duration: 6 hours

Difficulty: medium/high

Different abled accessibility: no

Suitable for children: yes

Difference in level: 560 metres


Other important information at the bottom of the page (or click here)

Un cammino tra i castelli del Chianti senese

By the hiking throughout Sienese Chianti Castles you will experience the exciting discovery of a magical territory, known and appreciated all over the world for its wine and its rustic buildings and which owes its charm to an important component that still distinguishes its landscape: fortifications.

In fact, being an obligatory place of passage for travellers who passed inland from the Valdarno, Chianti has been defined over the centuries in its territorial borders, disputed above all by Florence and Siena, and therefore characterised by a military architecture that still today marks its profile.

Since reaching the places of war and the guard did not happen by fast means – as happens when you come here only to visit the cellars or villages – it is through the slow path that you can see all the passages, every view that therefore makes us understand how the territory was guarded and crossed by the men of the past. What better thing then than discovering Chianti through an hiking crossing its castles?!?

hiking sienese chianti castles

One of the towers visible on the path

The starting point of our Hiking throughout Sienese Chianti Castles is Gaiole in Chianti, an ancient market place located in the valley of the Massellone stream, forty minutes from Siena. The first kilometres of our journey is one of the most difficult stretches of the entire route, since we will have to face 320 metres of altitude difference over a distance of 5 kilometres. Going towards Montegrossi, one of the oldest castles in the whole area of which today only one tower remains, you will be surprised by the dizzying view of an ancient stone quarry that is located on the way. Valdarno, which now, after the many curves and gorges you have faced – even if only to reach the starting point of the trek – you can see that it opens up in all its grandeur, crowned by the majestic Pratomagno.

Reaching Coltibuono Abbey

Leaving an area exposed to the sun, we embark on our Hiking throughout Sienese Chianti Castles on a shady road, covered in the shade by oaks and firs to reach, after climbing a few meters, the Badia a Coltibuono.

Monastery of Vallombrosan foundation, the Abbey today presents itself with its Romanesque church and the bell tower which is really massive and more reminiscent of the shape of a fortified structure, as indeed it must have been since this valley is one of the most exposed to raids that could come from the nearby Valdarno.

We will visit the interior of the church and you will have the opportunity to discover the fascinating history of the Benedictine reform carried out by a great local figure, San Giovanni Gualberto, who lived in the twelfth century.

After visiting the church it will be possible to stop for a lunch break. We will start again with our Hiking throughout Sienese Chianti Castles to take a beautiful path in the woods, where the fact that a Vallombrosan monastery has existed here for centuries is tangible thanks to the fir still present in an important extension, mixed with the oaks that show themselves with a much more varied colours than conifers, thanks also to lichens. Climbing the path we will reach the highest point of our route, where we will touch 700 metres of altitude.

Ruins Montegrossi Castle

hiking sienese chianti castles

 Vertine village

We will then descend quickly to cross only the asphalt for one point – it is the road to Radda – and then continue along the CAI path. After a few hundred metres we come across the site of an important archaeological find: Cetamura has returned interesting finds dating back to the Etruscan era that testify to the commercial and archaeological liveliness of this area. After a path in the woods we find ourselves in front of the view of the ancient castle of San Donato in Perano, already documented in medieval times. Today a very beautiful villa that dominates the landscape, we will have the view of it by crossing a wide road where the landscape will have changed, where the forest has given way to symmetrical rows of vineyards hundreds of metres long and which develop along the spectacular valley. We will now be close to almost sunset and it will be nice to savour the atmosphere of this long walk.

Vertine Castle

Continuing with our Hiking throughout Sienese Chianti Castles, suddenly the fortified village of Vertine will appear in front of you behind a curve.

A place already attested in the Middle Ages, of this pretty village, cared for down to the smallest detail by its few inhabitants, you will love its amenities and it will make you want to not want to leave this place.

We will conclude our Hiking throughout Sienese Chianti Castles and reestablish towards Gaiole, thus returning to the starting point. On the downhill road there are numerous glimpses for beautiful photos, from the Pieve di Spaltenna – one of the oldest in the area – to the small village of Barbischio, perched in a small cove behind Gaiole.

Once back in the village, it may be time for an aperitivo enjoying the fresh evening air, when the sun has already set behind the mountains and even the last blushes of the sky have faded. A drink is possible in one of the historic cafes of the place, with a characteristic country style that is due to the celebration of the Eroica, a very famous historic cycling competitions.

The day is drawing to a close and the memory that you will take home, once you feel your legs heavy when you get into the car, is the unknown story of a Chianti that is not that of its cellars but that of castles and knights who competed for the control of this middle earth.

hiking sienese chianti castles

Panoramic view on Valdarno

Pieve di Spaltenna

Barbischio village

Important information about the hiking (click here)

This hiking 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 is organised in collaboration with Ambra Tour Guide.

The activity here proposed, provided in English language, is a private and not a joinable hiking; 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 Hiking throughout Sienese Chianti Castles

The duration of the Hiking throughout Sienese Chianti Castles proposed here is 6 hours. The duration and the route can be adapted to the needs of the customers.

Trekking shoes and a layered outfit are recommended for the route.



Packed lunch break

There will be a mid-way lunch / snack break, with packed lunch. The hiking guide is not a tourist agency, so he/she does not provide a tasting, lunch or dinner reservation service but can suggest places where customers, if interested, can book.



Insurance coverage

The hiking guide or guides who carry out this activity are covered by liability insurance. The meeting point for the beginning of the activity coincides with the final point since it is a trekking with a circular route.



Badia a Coltibuono opening hours:

As the opening hours depends on the availability of a volunteer opening the church, please contact the guide in advance to verify the opening.

Open every day 9:00am – 7:00pm



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:

info@guidaturistica-michelebusillo.com, also by Whatsapp o Telegram


Go back to the Itinerary description

Cost and reservation of the tour (click here)


Cost of the Hiking

The cost for a trek throughout the Chianti castles, for a total of 6 hours, is € 280.00 (total price 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).

Back to the description of the itinerary

How to reach the starting point of the hiking? (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 organised with an agency) is still the most convenient way to do the entire itinerary.

Gaiole in Chianti, the starting point of the trek, can be reached via the A1 motorway (Valdarno exit if you come from Rome or Milan; then continue following the signs towards Terranuova Bracciolini, then for Gaiole, or exiting on the A1 motorway at Bettolle-Valdichiana, continue to Siena and then take the SP 408 to Montevarchi.

Free parking spaces are available in Gaiole in Via Galileo Galilei, along Via Alighieri and Via Baccio Bandinelli.


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 Gaiole in Chianti is, besides a rented car:


By Taxi

To reach Gaiole in Chianti, the Siena taxi service is available and can be contacted at +39057749222 by sending an SMS to +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 is drop-off/drop-on point for passengers in Gaiole in Chianti (click here to view the points).


By camper van

For camper owners there is a dedicated area in the centre of Gaiole in Chianti. For more info on the areas dedicated to campers click here.


Go back to the Itinerary description