4.4
(430)
4,086
riders
40
rides
Touring cycling around Chiusdino is set within the Sienese hills of Tuscany, characterized by rolling terrain and diverse landscapes. The region features the Merse Valley and the Metalliferous Hills, offering varied elevations and scenic backdrops. Dense forests of holm oaks, cork oaks, and maple trees are common, particularly within the Alto Merse Regional Nature Reserve, alongside numerous vineyards. This area provides a mix of challenging climbs and picturesque routes through a rich natural environment.
Last updated: May 11, 2026
5.0
(3)
28
riders
33.9km
02:38
610m
610m
Hard bike ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.6
(8)
84
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4.5
(12)
70
riders
32.4km
02:15
560m
560m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.5
(12)
60
riders
35.3km
02:17
450m
450m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(3)
52
riders
67.5km
04:28
900m
900m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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The perimeter walls are still partially visible, especially in the southern section, where an arched gate surmounted by three rounded stones stands. At the highest point of the hill stands the imposing stone keep, which extends around a courtyard. Within the walls is the church of Santa Maria Assunta, dating back to the 13th century but completely renovated in the late 19th century. It has a distinctive urban layout, dominated by an imposing stone keep arranged around a courtyard accessed through two round-arched gates, defended by a large tower with a massive base.
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Chiusdino is a wonderful medieval village located in the Merse Valley among the Metalliferous Hills. Its origins date back to the Lombard domination of Tuscany between 568 and 569. The town still retains its medieval appearance and some sections of the double city walls. It is also possible to find medieval houses, including the alleged house of San Galgano (Galgano Guidotti), where the saint is believed to have been born around 1150.
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Chiusdino is a wonderful medieval village located in the Merse Valley among the Metalliferous Hills. Its origins date back to the Lombard domination of Tuscany between 568 and 569. The town still retains its medieval appearance and some sections of the double city walls. It is also possible to find medieval houses, including the alleged house of San Galgano (Galgano Guidotti), where the saint is believed to have been born around 1150.
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The Montesiepi Hermitage was built immediately after the saint's death, over the ancient hut where San Galgano lived during his last year (1181). The hermitage was consecrated in 1185 by the bishop of Volterra, Ildebrando Pannocchieschi. The small complex consists of the circular church interrupted only by the small apse, the chapel with frescoes by Lorenzetti, and the entrance porch. In the porch, look down to the left and look for an "original" medieval plaque that reminds the pilgrim... that he must die and that life is short. The original church was circular, then the entrance hall was added in 1200. The bell tower and Lorenzetti's chapel were added in the following century. The rectory dates back to the 18th century. The dome, constructed from alternating rows of white stones, is extremely elegant. Inside the Hermitage, in the center of the Rotonda, there is the famous Sword of San Galgano, stuck in the rock for over 800 years.
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Every August 14th the Palio dei Ciuchi takes place, a very heartfelt folkloristic event where the five districts (Corso, Ventosa, Torre, Tramonto and Nobili) compete for a banner painted by local artists. During the same month, "Medioevo nel Borgo" is also organized, a suggestive medieval festival known throughout Tuscany with jugglers, musicians, acrobats and stalls with artisanal products, for a leap into the past.
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Roccatederighi stands on a spur of Mount Sassoforte, from which you can enjoy a wide and splendid panorama of the Maremma. The town still retains its medieval charm intact, in addition to the suggestive arched entrance gate and some tower houses. But the peculiarity of this village is given by the close link it has with the rock on which it rests, trachyte, a volcanic rock that has been exploited to build houses and other buildings, dig alleys and squares, and of which boulders and outcrops can be seen in various parts of the center. you can also find the remains of the ancient fortress and some sections of the original walls, dating back to the fourteenth century. In the upper part stands the tower, rebuilt in 1910 with a large clock that marks the time of this corner of Tuscany.
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Built in the 13th century in Gothic style and dedicated to the saint from Chiusdino, today it is completely in ruins: only the walls remain standing, with the apse still in evidence, perfectly facing east, while on the upper part of the facade there are two pointed windows. The roof of the Abbey of San Galgano is no longer there today. The "official" version says that it deteriorated and then fell over the centuries, while an alternative version, according to some legend and according to others truth, states that it was originally made of lead, and was sold by Girolamo Vitelli in 1550. Whatever the truth behind the roof of the abbey, after some restoration attempts that went badly, at the end of the 18th century it was deconsecrated and left to the elements until the present day. The ruins of the Abbey of San Galgano, with its profile still intact and immersed in the Tuscan countryside, offer a truly incredible and particular view. In addition to the roof, the floor is also missing, which during the summer turns into a grassy blanket, while you can still see a transept with three naves and 4 chapels with cross vaults. Next to the Abbey of San Galgano there is the cloister, which was rebuilt at the beginning of the last century, using the original materials. Some accessory rooms are also very beautiful, which can also be visited with the entrance ticket to the abbey, including the chapter house, where the monks originally met to deliberate the main rules of the community, and the scriptorium, which was the place where the monks copied the manuscripts.
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There are over 40 touring cycling routes around Chiusdino. These routes offer a variety of experiences, with 9 classified as moderate and 31 as difficult, catering to different fitness levels.
Chiusdino is situated in the Sienese hills, meaning you can expect rolling terrain with significant elevation changes. Routes often traverse the Merse Valley and the Metalliferous Hills, featuring both challenging climbs and scenic descents through dense forests and vineyards. For example, the Chiusdino and Monticiano — Ring tour includes over 600 meters of elevation gain.
While many routes in Chiusdino are classified as difficult due to the hilly terrain, there are 9 moderate routes available. These routes still offer a good workout but are generally less demanding than the most challenging options, making them suitable for touring cyclists looking for a slightly less strenuous experience.
Many routes integrate historical and natural attractions. You can cycle past the iconic Abbey of San Galgano and the nearby Hermitage of Montesiepi, which houses the legendary 'Sword in the Stone'. The area also features medieval villages like Chiusdino itself, and natural highlights such as the Canaloni Waterfall and Natural Pools. The San Galgano – Montesiepi Hermitage loop from Hapimag Parkplatz P1 is a great option to visit these sites.
Yes, many of the touring cycling routes in Chiusdino are circular, allowing you to start and end at the same point. Examples include the Chiusdino and Monticiano — Ring tour and the Chiusdino Historic Center – Chiusdino loop from Chiusdino, which both offer convenient loop options.
The spring and autumn months are generally ideal for touring cycling in Chiusdino. The weather is milder, and the Tuscan landscape is particularly beautiful, with blooming wildflowers in spring and vibrant colors in autumn. Summers can be quite hot, especially in July and August, while winters can be cooler and wetter.
Absolutely. The Sienese hills provide numerous panoramic viewpoints. Routes often pass through picturesque vineyards and offer breathtaking vistas of the rolling Tuscan countryside. The Chiusdino and Monticiano — Ring tour is known for its expansive views of the Sienese hills.
The touring cycling routes around Chiusdino are highly rated by the komoot community, with an average score of 4.4 stars from over 80 reviews. Cyclists often praise the diverse landscapes, the combination of physical activity with cultural exploration, and the well-preserved medieval charm of the villages.
Yes, for experienced touring cyclists seeking a greater challenge, routes like the Tatti Village – San Galgano loop from Chiusdino offer significant distances and elevation gains. This particular route covers over 67 kilometers with nearly 900 meters of ascent, providing a demanding yet rewarding experience through the Tuscan countryside.
For more general information about Chiusdino and its offerings, you can visit the official tourism website for Tuscany: visittuscany.com/en/towns-and-villages/chiusdino/.
Yes, you can explore the charming medieval architecture of Chiusdino's historic center by bike. The Chiusdino Historic Center – Chiusdino loop from Chiusdino is specifically designed to navigate through the cobblestone streets and historic buildings of the village, offering a unique cultural cycling experience.
Many routes connect Chiusdino with other charming villages in the region. For instance, the Chiusdino and Monticiano — Ring tour links Chiusdino with Monticiano, allowing you to experience the unique character of multiple historic Tuscan settlements in one ride.


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