4.5
(1718)
15,247
riders
76
rides
Touring cycling routes around Castiglione D'Orcia traverse the UNESCO World Heritage-listed Val d'Orcia, characterized by undulating hills, cypress trees, and olive groves. The region offers varied terrain, from the clay expanses of the Crete Senesi to the more mountainous areas at the foothills of Mount Amiata, featuring thick forests. Routes often follow rivers and pass by natural thermal springs, providing diverse landscapes for cyclists.
Last updated: May 11, 2026
4.8
(122)
510
riders
42.1km
03:18
780m
770m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.7
(3)
65
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4.6
(30)
226
riders
60.0km
04:21
980m
980m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
55
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
50
riders
123km
09:40
1,960m
1,960m
Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.
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Pretty here, very pretty
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Pretty here, very pretty
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Little-trafficked asphalt road in the south of the Val d'Orcia
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Chiesa di Santa Maria Assunta The church, dating to the twelfth century, has a plain rectangular plan with a wall covering in square stones. Outside the massive portal is embellished with decorations, maybe originating from the Abbazia di Sant'Antimo. The gabled bell tower and the vestry are original, too. The apse is crowned with corbels and decorated with suspended arches. On the left side there is another monumental portal whose arch is supported by two columns and contains a decorated shape. The extremely plain interior is lit up by narrow slits, one in the apse.
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Now part of the Collection https://www.komoot.com/de-de/collection/3600632/-naturdenkmaeler-besondere-baeume-und-weitere-schaetze-der-natur
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A characteristic and panoramic rest point on the Via Francigena, where bikers, pilgrims and travellers share moments of relaxation in company.
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centuries-old oak tree that tells and tells us its "value"
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There are over 70 touring cycling routes around Castiglione D'Orcia, offering a wide range of experiences through the Val d'Orcia landscape.
The routes vary significantly. While there are a few easy options and 16 moderate routes, the majority (56 out of 74) are classified as difficult, often featuring significant elevation gains and unpaved sections. These challenging routes are ideal for cyclists with very good fitness.
Yes, many of the touring cycling routes in the area are designed as loops, allowing you to start and finish in the same location. For example, the Pienza – I Cipressini Farmhouse loop from Bagno Vignoni is a popular circular option, offering stunning views of the Val d'Orcia.
You'll experience the iconic UNESCO World Heritage-listed Val d'Orcia, characterized by undulating green hills, cypress trees, picturesque farmhouses, vineyards, and olive groves. Routes also offer views of the unique clay expanses of the Crete Senesi and the more mountainous terrain with thick forests at the foothills of Mount Amiata.
The region is rich in attractions. You can cycle past medieval villages like Pienza and Montalcino, or explore natural wonders. Highlights include the impressive Radicofani Fortress, the captivating limestone formations of The White Whale (Bagni San Filippo), and the ancient Bagno Vignoni Thermal Springs. Many routes also offer panoramic views from spots like View from Monte Amiata.
Absolutely. For experienced riders seeking a significant challenge, the View of Val d'Orcia – Buonconvento loop from Monte Amiata is a demanding route covering nearly 100 km with almost 1900 meters of elevation gain, taking around 8 hours to complete. Another challenging option is the Pienza – Monticchiello loop from Bagno Vignoni, which is 68.3 km long with over 1100 meters of ascent.
The area is highly rated by the komoot community, with an average score of 4.4 stars from over 240 reviews. Cyclists often praise the stunning Val d'Orcia landscapes, the variety of terrain from rolling hills to more mountainous sections, and the charming medieval villages encountered along the way.
The mild climate of Val d'Orcia makes it suitable for cycling for much of the year. Spring and autumn generally offer the most pleasant temperatures and vibrant scenery, with fewer crowds than peak summer. Summer can be warm, but early mornings or late afternoons are still enjoyable.
Yes, the region is famous for its wines and olive oil. Many routes traverse vineyards, particularly around Montalcino, known for its Brunello wine. The Orcia Wine Trail also passes through Castiglione D'Orcia, offering cyclists a chance to discover local products like DOC Orcia Wine and Extra Virgin Olive Oil.
Yes, many routes in the Val d'Orcia feature gravel sections, adding to the adventure. The Val d'Orcia Gravel Route – Spedaletto Castle loop from Gallina is a prime example, offering a challenging ride through scenic gravel paths and past historic castles.
Yes, the region is known for its natural thermal areas. The Historic Village of Radicofani – Historic centre of Radicofani loop from Bagni San Filippo starts near Bagni San Filippo, which features free, open-air thermal spas with unique limestone formations and waterfalls. Bagno Vignoni is another well-known thermal town often included in routes.


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