Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Cycling routes
Italy
Tuscany
Siena

Chiusdino

The best cycling routes around Chiusdino

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.

Best touring cycling routes around Chiusdino

Last updated: May 11, 2026

5.0

(3)

28

riders

#1.

Chiusdino and Monticiano — Ring tour

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.

Navigate with device

Send to Phone

Save

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
Sign up for free to see 36 more rides around Chiusdino.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Chiusdino

Road Cycling Routes around Chiusdino

Hiking around Chiusdino

MTB Trails around Chiusdino

Running Trails around Chiusdino

Gravel biking around Chiusdino

Tips from the Community

Stenio Melani
February 9, 2026, Tatti Village

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.

Translated by Google

0

0

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.

Translated by Google

0

0

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.

Translated by Google

0

0

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.

Translated by Google

0

0

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.

Translated by Google

1

0

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.

Translated by Google

1

0

Chiara
May 4, 2025, Tatti Village

beautiful hamlet of Roccastrada

Translated by Google

0

0

Dona&Leo
April 15, 2025, San Galgano

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.

Translated by Google

2

0

Frequently Asked Questions

How many touring cycling routes are available around Chiusdino?

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.

What kind of terrain and elevation can I expect on touring cycling routes in Chiusdino?

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.

Are there any easy or beginner-friendly touring cycling routes in Chiusdino?

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.

What historical sites and natural landmarks can I see along the touring cycling routes?

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.

Are there any circular touring cycling routes around Chiusdino?

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.

What is the best time of year for touring cycling in Chiusdino?

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.

Can I find viewpoints or scenic spots along the touring cycling routes?

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.

What do other touring cyclists say about the routes in Chiusdino?

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.

Are there any longer, more challenging touring cycling routes for experienced riders?

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.

Where can I find more information about Chiusdino as a destination?

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/.

Are there routes that explore the historic center of 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.

Are there any routes that connect Chiusdino with other nearby villages?

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.

Most popular routes around Chiusdino

Road Cycling Routes around Chiusdino

Most popular attractions around Chiusdino

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Cycling routes in other regions.

MontalcinoBuonconventoSan Quirico D'OrciaColle Di Val D'ElsaGaiole In ChiantiMonteroni D'ArbiaPienzaAscianoMontepulcianoMonteriggioniSan GimignanoCastelnuovo BerardengaRiserva Naturale Del Bosco Di Sant'AgneseCastiglione D'OrciaPoggibonsiCastellina In ChiantiRadda In ChiantiSovicilleTrequandaRapolano TermeChiusiCasole D'ElsaRiserva Naturale Di CastelvecchioMurloSinalungaChianciano TermeRiserva Naturale Alto MerseSan Giovanni D'AssoRiserva Naturale PietraporcianaRiserva Naturale Basso MerseRiserva Naturale Lucciola BellaSarteanoSan Casciano Dei BagniPiancastagnaioRiserva Naturale Cornate E FosiniRiserva Naturale Il BogattoRiserva Naturale Crete Dell'OrciaMonticianoLago di MontepulcianoRiserva Naturale Lago di MontepulcianoRadicondoliTorrita Di SienaRadicofaniCetonaRiserva Naturale PigelletoLake ChiusiAbbadia San Salvatore

Nearby adventure guides

Things to Do in Riserva Naturale Alto Merse

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy