Trekking to Monteriggioni and to the other dantesque castles

trekking monteriggioni
  • Abbadia Isola Monastery

  • Sapia Salvani’s Castle

  • Panoramic view on Monteriggioni

  • Monteriggioni Castle

  • Ancient route of the Via Francigena

  • Section of the Montagnola paths

Tour duration: 4/5 hours
Difficulty: medium
Suitable for children: yes

Total distance: 10,9km

Difference in level: 160 mt


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


A trekking between Monteriggioni and the other Val d’Elsa castles

The trekking to Monteriggioni and the other dantesque castles of Val d’Elsa is an unmissable journey through the history of a wonderful area in the province of Siena. Although two of the three stages you will see on this route can be reached by car, it is only by a walking route that you are able to enjoy the suggestive views of a landscape that has preserved unchanged, for large stretches, the appearance it had in the Middle Ages.

Although with important testimonies since the Etruscan era, it is in the middle age that the Val d’Elsa experienced significant moments in its history and of which you will see the evident signs along the way: from the Via Francigena, connecting San Gimignano with Monteriggioni, to the fortified structures that served to defend the borders of the Republic of Siena, up to the castles of the local lords whose revenges described by Dante Alighieri in the Divine Comedy were perpetrated, this trek, lasting about five hours, is truly an exciting journey into history, however, surrounded by nature.

Abbadia Isola, a jewel of the Romanesque

Our trek will start from Abbadia to Isola, an ancient monastery founded in 1001 which still retains in its name an ancient feature of the place where it stands. We visit the abbey church of San Salvatore and Cirino, an illustrious example of Romanesque architecture in the area. Among the works of particular importance still preserved inside, we go to see a fresco by Vincenzo Tamagni with the iconography of the local cult of the Madonna della Cintola; then we see a beautiful baptismal font reminiscent of the dynamism of Giovanni Pisano.

trekking monteriggioni

A moment of the trekking

A mysterious capital …

On the main altar of the church you then have the opportunity to observe the fifteenth-century altarpiece, painted by the Sienese artist Sano di Pietro, where the scenes of the predella feature the events of the saints particularly dear to local devotion as well as to the Benedictine order monks that for centuries have taken care of this sacred place. Before leaving the church, we still have the opportunity to dwell on two rather singular and ‘mysterious’ works: a Roman aged urn with an inscription concerning the conservation of San Cirino’s remains and finally a Romanesque capital with the presence of two men holding their hands raised, above which a spiral shape resembles that of a snake: it is an image with a strong symbolic content and that we will see together.

Castiglion Ghinibaldi

Once left Abbadia a Isola, we set off towards Castiglion Ghinibaldi, the second step of our Trekking to Monteriggioni and to the other dantesque castles of Val d’Elsa.

Shortly before arriving at the castle, a panel show us the place where there was a battle in the mid-13th-century: the so-called “battaglia del canneto” (battle of the reeds) involved the monks of Abbadia Isola, the community of Monteriggioni and the Municipality of Siena … we will find out more in detail about what happened.

We take an uphill road, where the difference in height is close to 30 metres over a distance of 500 metres. At the end of climb, we find ourselves facing the fascinating abandoned castle known by the name of “Castiglion Ghinibaldi“. Dating back to the 13th-century in its original nucleus, the structure takes its name from Ghinibaldo Saracini, an important businessman who married the Sienese noblewoman Sapìa Salvani in the first half of the 13th-century. If the story of Ghinibaldo is common to that of many other men of his time who made their fortune thanks to trade, it is that of Sapìa to ibe irresistibly intriguing, especially because Dante Alighieri talks about her in the 13th Canto of Purgatory, where poet meets her in the frame of the envious: the noblewoman is atoning her sentence for having plotted a revenge against her nephew Provenzano Salvani. As we reread the passages of the Divina Commedia, also reported in an inscription of the castle, you will disclose the revenge that right here was perpetrated: we will see what happened in this place in 1269 …

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The internal space of di Abbadia Isola Monastery

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Castiglion Ghinibaldi

After having seen the outside of Castiglion Ghinibaldi (unfortunately it is not possible to visit it inside because the castle is abandoned and unsafe in some internal environments) we descend towards the plain to reach the last stage of our trekking to the castles of Val d’Elsa : Monteriggioni.

Reaching the entrance to the castle take you along another 250-metres long uphill road with a vertical drop of 25 metres. The sudden speed of the path may surprise you, but fortunately it is a matter of a few distance, because in front of you you will see the solemn medieval gate of Monteriggioni ever closer. This castle represents a unicum in the series of fortified structures found in the area: it is not simply a village that is equipped with a wall, but an articulated fortified structure, with an elliptical shape, built completely from scratch in an area where the ancient Republic of Siena needed to defend itself from the continuous incursions of the rival Florence.

Between the walls of Monteriggioni

If once you have crossed the threshold of the castle entrance, this sort of citadel seems small and quick to visit, it will surprise you instead to know its history, made up of many small but important episodes that have changed the destiny not only of Monteriggioni, but above all that of the surrounding area: it is the incredible story made up of men and women loyal to a cause, of pretentious monks, of captains of fortune willing to do anything to save honour, of many workers busily engaged in the hard work of building the walls , and finally of blacksmiths with an unlikely and amusing name.

Once you have finished visiting Monteriggioni and having told you its story, you will have some free time to bring a souvenir with you, as well as to climb the castle walls, equipped with a special modern walkway, to admire the surrounding landscape that allows you to the east. to see the town of Castellina in Chianti, while to the West it makes you glimpse the unmistakable towers of San Gimignano.

When we leave Monteriggioni, we take a path in the woods that corresponds to the ancient route of the Via Francigena, still today traveled by thousands of pilgrim and traveler every year. In the wood, mainly characterized by scrub vegetation, we can notice a peculiarity of the soil of this area: a red soil that can be seen lying on a ground mainly composed by cavernous limestone. The path in the woods also gives the possibility of finding where once there were small medieval villages with an agricultural vocation, as well as the points where in recent years some Etruscan chamber burials have been identified.

After the wood, the road returns to the level: a few hundred metres are missing to return to Abbadia a Isola, the starting point; as indication of the journey ending you will find an oak tree, already encountered on the outward leg but which you will now notice more because the time of sunset is approaching…

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The mysterious capital of Abbadia a Isola

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On the way towards Monteriggioni

Trekking Monteriggioni

Some moments of val d’Elsa Hiking castles

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 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.



Trekking duration of Monteriggioni and the castles of Val d’Elsa

The duration of the trek can be 4 hours or 5 hours: with a 4-hour trek we can visit the Abbadia a Isola complex and the interior of the Monteriggioni castle. With a 5-hour trek we can also visit Castigion Ghinibaldi

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.




Opening time Abbadia Isola Monastery:

From April 1st to October 31st 

10:00am – 1:00pm

3:00pm – 6:00pm

From November to March 31ston request


More info on Monteriggioni and the Abbadia Isola complex, click here to visit the official website of Monteriggioni turismo 


To visit the Complex of Abbadia Isola there is currently no ticket but an offer is welcome and that facilitates the work of the volunteers who undertake to keep this important symbol of the Via Francigena as well as a local Romanesque architecture testimony. The sum of the offer is included in the hiking rate.

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 or Telegram


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Cost and reservation of the hiking trail (click here)


Cost of the hiking

The cost for 4 hours of hiking trail is € 210.00 (price in total and not per person), for 5 hours € 270.00 (always price in total and not per person). The rate includes the contribution that is appreciated to leave for the opening of the Abbadia Isola complex.

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



How to book the hiking trail?

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 Abbadia Isola?

By Car

Reachable via the A1 motorway (Siena-Bettolle exit if coming from Rome; Florence-Impruneta exit if coming from Milan; then continue towards Siena and exit at Monteriggioni; from here head towards Abbadia Isola. Free parking areas are in front of the Abbadia Isola complex. Another lager area is very close by (click here to view it)


By public Bus

To reach Abbadia Isola by bus there is an extra-urban line from Siena (130 As) direct to San Gimignano (see here the timetables of the return lines Abbadia Isola – Siena).

However, the bus does not pass precisely at Abbadia Isola but remains on the trajectory of the Via Cassia. The closest stop to Abbadia Isola is Pian del Casone; from here continue on foot for 10 minutes to get to Abbadia Isola.


By train

The starting point of the hiking can be reached by train with the Trenitalia service, thanks to the regional lines. The closest station is Castellina Scalo (far 50 minutes by walking, 15 by bike riding) or Siena. Once you arrive at the Siena railway station, you can reach Abbadia Isola:


By Bus

Via the 130 AS line (see above). For a real-time consultation, visit the Autolinee toscane website.


By Taxi service

Siena taxi service is available for the area and it 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 Abbadia Isola (click here to view the point).


By camper van

Camper owners find rest areas around Monteriggioni. There are the “La Posta” and “Il Cipressino” areas. Other areas closer to Siena are the area called Fagiolone. This is an equipped area with video surveillance (for more info click here). Other rest areas are in Fontebecci and in the Palasport Mensana area. Another equipped area is Camping Siena Colleverde.



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