4.3
(485)
4,919
riders
56
rides
Touring cycling around Sinalunga offers diverse landscapes within the Val di Chiana, characterized by rolling hills, vineyards, and olive groves. The region features both paved and gravel roads, including sections of the historic "strade bianche" in the Crete Senesi. Elevations vary, providing routes from generally flat paths like the Sentiero della Bonifica to more challenging climbs through undulating terrain. This area provides varied conditions for touring cyclists.
Last updated: May 11, 2026
149
riders
46.1km
04:29
1,020m
1,020m
Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.
5.0
(5)
54
riders
47.8km
03:17
840m
840m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4.4
(5)
41
riders
54.2km
03:31
700m
700m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.2
(5)
29
riders
48.7km
03:26
760m
760m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.7
(3)
30
riders
43.1km
02:54
600m
600m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Sinalunga
200 km in Valdichiana Senese – ride through the centuries in Tuscany
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The Collezione Pallavicini di Trequanda Archaeological Collection is a small but precious exhibition space that tells the oldest history of the territory. Housed in the historic center of the village, the collection brings together Etruscan and Roman artifacts from the area, a testament to the human presence and cultural vitality of these lands since antiquity.
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The tunnels of Sinalunga, built in the 13th century to channel water from the Pozzo di San Martino to the Fonte del Castagno, represent an important work of medieval engineering. Today they offer a suggestive underground route. *Check the website for opening hours to have the experience
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The Collegiata di San Martino, in the center of Sinalunga, is an important church for the town's history. Externally, it presents simple lines, while the interior is richer, with various valuable works of art. It testifies to the religious and cultural life of the community over the centuries, remaining a landmark for the village to this day.
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Very cool place for water refilling. Nice artwork.
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Tip: Have a coffee or an ice cream at Bar l'Angolo. The staff is friendly and cheerful, and there are shady spots under the trees.
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Definitely worth the trip.. beautiful scenery at every turn!
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Not a lot to do, but a quaint little church that provokes a sense of history. Very cool!
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There are over 50 touring cycling routes around Sinalunga, offering a wide range of experiences for different skill levels. The komoot community has explored these routes over 600 times, contributing to an average rating of 4.1 stars.
Yes, Sinalunga offers several easier routes. The region's generally flat roads and dedicated paths are ideal. A notable option is the "Sentiero della Bonifica," a 60-62 km traffic-free cycling and pedestrian path along the Canale Maestro della Chiana, perfect for families and e-bike users. While specific easy routes are not listed in the top recommendations, 4 routes are classified as easy within the region.
The terrain around Sinalunga is diverse. You'll find a mix of generally flat roads in the Val di Chiana, undulating hills with gentle climbs and descents, and the famous 'strade bianche' (gravel roads) in the Crete Senesi. Routes like Strada di Monte Sante Marie – Monte Sante Marie Gravel Road loop from Rigomagno will introduce you to these iconic gravel sections.
Sinalunga's routes offer numerous scenic points and historical landmarks. You can enjoy expansive views across the Val di Chiana on routes like View of Baccoleno – Beautiful scenic viewpoint loop from Sinalunga. The distinctive 'lunar landscape' of the Crete Senesi is a highlight, visible on tours such as Beautiful scenic viewpoint – View of the Crete Senesi loop from Sinalunga. Other attractions include the Asciano Historic Center and the charming Montefollonico Medieval Village.
Yes, many of the touring cycling routes around Sinalunga are designed as loops, allowing you to start and end in the same location. Examples include Scenic Descent – Porta di Rigomagno loop from Sinalunga and Porta di Rigomagno – Scenic Descent loop from Sinalunga, which offer varied distances and elevations.
Sinalunga is ideal for cycling during spring and autumn when the weather is mild and the landscapes are particularly vibrant. These seasons offer comfortable temperatures for longer rides and allow you to fully appreciate the vineyards, olive groves, and fertile lands of the Val di Chiana.
Absolutely. The Tuscan section of the ancient Via Lauretana has been developed into a cycling path, linking Siena to Cortona and passing through towns like Asciano and Sinalunga. This route features both asphalted and dirt sections, offering a blend of history and scenic beauty. You can also connect to sections of the historic Via Francigena from the Via Lauretana.
The komoot community highly rates the touring cycling experience in Sinalunga, with an average score of 4.1 stars. Reviewers often praise the diverse landscapes, from the fertile Val di Chiana to the unique 'strade bianche' of the Crete Senesi, and the opportunity to explore charming medieval villages and historic farms along the way.
Yes, Sinalunga and the surrounding Valdichiana region are well-equipped for cyclists. You can find bike rental services that offer a range of bicycles, including road, gravel, mountain, and e-bikes, catering to various preferences and fitness levels.
Yes, Sinalunga offers numerous challenging routes with significant elevation changes. For example, the Scenic Descent – Porta di Rigomagno loop from Sinalunga is a difficult 45.7 km trail featuring over 1000 meters of elevation gain, providing a demanding ride for experienced touring cyclists.
The region boasts several natural highlights. The Val di Chiana itself is characterized by vineyards, olive groves, and orchards. Nearby, you can explore the Crete Senesi scenic route with its unique 'lunar landscape.' The Valdichiana Senese also includes nature reserves like the Pietraporciana Nature Reserve and the Montepulciano Lake Nature Reserve, offering tranquil spots and wildlife observation.


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