4.4
(269)
2,822
riders
20
rides
Touring cycling around Monticiano offers diverse routes through a landscape characterized by rolling hills, ancient forests, and significant river valleys. The area is nestled in the hills of Siena, providing varied terrain for cyclists. Key natural features include the Merse and Farma rivers, which nourish extensive forests and form nature reserves. Cyclists can expect a mix of paved and unpaved surfaces, with routes often involving climbs to hilltop towns.
Last updated: May 11, 2026
5.0
(4)
43
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(4)
23
riders
28.3km
02:11
440m
440m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3.0
(2)
20
riders
51.9km
03:46
1,160m
1,160m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
15
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.5
(2)
15
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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The Cippo is located at the entrance of the Strada Bianca on the SP99 side
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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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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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A great view of the surrounding mountains.
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This church is dedicated to Saint Giusto, Bishop of Volterra, and his priest brother Clemente. According to legend, it would arise on the ruins of the Temple of Gianus, from which the name of the village derives, Monte di Giano, which later became Monticiano. The church was built in the early 1200s in Romanesque-Gothic style. The façade is made of limestone of various colors, with a portal crowned by a round arch. On the architrave of the portal is carved a braid pattern, as in the side door, which is decorated with a bull's head and a snake holding a lily in its mouth. These decorations come from the Romanesque and Lombard tradition and date back to the twelfth century. At the back of the church stands a sail bell tower from the sixteenth century.
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There are over 20 touring cycling routes around Monticiano, offering diverse options for exploring the region. These routes range from moderate to difficult, catering to various skill levels.
The terrain around Monticiano is characterized by rolling hills, ancient forests, and significant river valleys. You can expect a mix of paved and unpaved surfaces, with many routes involving climbs to hilltop towns that offer rewarding panoramas of the classic Tuscan landscape.
Monticiano's mild climate, even in summer, makes it suitable for touring cycling for much of the year. The lush forests of oak, chestnut, and pine trees ensure pure, healthy air. Spring and autumn generally offer the most pleasant temperatures for longer rides, while summer provides opportunities for refreshing dips in river pools like the Canaloni del Farma.
Yes, many touring cycling routes around Monticiano are circular, allowing you to start and end in the same location. An example is the Chiusdino Historic Center – Historic Center of Monticiano loop from Monticiano, which takes you through medieval villages and offers scenic views.
While many routes around Monticiano are rated moderate to difficult, there are options that can be enjoyed by less experienced cyclists. For example, the San Galgano – Montesiepi Hermitage loop from Scalvaia is a moderate route that allows you to experience the area's beauty without extreme challenges.
Cycling routes often pass through the Merse and Farma river valleys, which are part of nature reserves rich in biodiversity. You might encounter the Canaloni Waterfall and Natural Pools, perfect for a summer dip. The Petriolo Thermal Baths and Bagni di Petriolo Hot Springs, known since Roman times, are also notable natural monuments in the vicinity.
Absolutely. Many routes lead past or near significant historical sites. The San Galgano – Montesiepi Hermitage loop from Scalvaia takes you to the magnificent roofless 13th-century Cistercian Abbey of San Galgano and the nearby chapel with the 'Sword in the Stone'. You can also explore charming medieval villages and castles like Bibbiano Castle or Murlo Historic Village.
Yes, Monticiano offers routes that incorporate gravel or dirt roads, providing a different cycling experience. The La Vidritta gravel – Ponte della Pia loop from Monticiano is a popular difficult route that features gravel sections and offers scenic views across classic Tuscan landscapes.
The touring cycling routes in Monticiano are highly rated by the komoot community, with an average score of 4.3 stars from over 180 reviews. Cyclists often praise the fantastic roads with 360-degree views of classic Tuscan landscapes, the challenging climbs to hilltop towns, and the serene experience of cycling through ancient forests and river valleys.
Monticiano and its surrounding villages typically offer parking options, especially in town centers or near popular trailheads. It's advisable to check local signage for specific parking regulations or designated areas before starting your ride.
For experienced cyclists seeking a challenge, routes like the View of Val d'Orcia – Historic Center of Monticiano loop from Monticiano offer significant elevation gains and longer distances. Another demanding option is the Pia Bridge – Sovicille Village Center loop from Riserva Naturale Basso Merse, which is a difficult route covering a substantial distance with considerable climbing.


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