4.6
(13)
202
riders
04:45
71.6km
940m
Cycling
This difficult 44.5-mile touring bicycle loop from Siena to Asciano offers challenging climbs and stunning views of the Crete Senesi.
Last updated: February 26, 2026
Tips
Includes a segment in which cycling is not permitted
After 3.16 km for 197 m
Waypoints
Start point
Parking
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3.59 km
Highlight • Historical Site
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4.64 km
Highlight • Monument
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9.00 km
Highlight • Trail
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20.1 km
Highlight • Historical Site
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36.6 km
Highlight • Historical Site
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48.9 km
Highlight • Viewpoint
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Tip by
71.6 km
End point
Parking
Way Types & Surfaces
Way Types
51.2 km
12.3 km
5.07 km
2.05 km
1.10 km
< 100 m
Surfaces
63.7 km
2.67 km
2.36 km
2.19 km
789 m
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Elevation
Highest point (340 m)
Lowest point (160 m)
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Weather
Powered by Foreca
Sunday 10 May
23°C
13°C
25 %
Additional weather tips
Max wind speed: 21.0 km/h
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This route was planned by komoot.
This loop tour is classified as difficult and requires very good fitness. You'll encounter significant elevation changes with numerous ascents and descents, some of which can be steep. The varied terrain, including unpaved sections and 'strade bianche,' adds to its demanding nature.
The route features varied terrain. While much of it is paved, you will ride on significant sections of unpaved roads, compacted gravel, and even some cobblestones. A distinctive feature is the presence of 'strade bianche,' the iconic white dirt roads of Tuscany. Be prepared for rolling hills and steep climbs.
You'll pass by several notable sights. In Siena, you can see the Palazzo Pubblico and Piazza del Campo and Porta Romana. The route also includes sections of the historic Via Francigena. Further along, you'll find the Historic Centre of Monteroni d'Arbia and the Historic center of Asciano. Don't miss the stunning View of the Crete Senesi.
Yes, the route overlaps with several official trails. You'll find sections that are part of the EuroVelo 5 - Via Romea Francigena - part Italy, Ciclovia Francigena - VFB17, Via Lauretana Toscana, Via Francigena - 06 Tuscany, and the famous Strade Bianche and L'Eroica routes.
Spring (April-May) and early autumn (September-October) are generally the best times. The weather is milder, and the Tuscan landscape is particularly beautiful. Summers can be very hot, making the challenging climbs even more demanding, while winters can be cold and wet.
No, there are no specific permits or entrance fees required to cycle this loop tour through the Crete Senesi. The area is largely open for public access. However, always respect private property and local regulations.
Given its 'difficult' classification, significant elevation changes, and varied terrain including unpaved sections, this loop tour is not recommended for beginners or families with young children. It requires very good fitness and cycling skills.
For starting in Siena, you can look for parking options near the city center or the train station. Parking availability can vary, especially during peak season, so it's advisable to arrive early or research specific parking garages in advance.
While there are no specific restrictions against dogs on the public roads and paths that make up this route, it's important to consider the challenging nature of the ride and the varied terrain. If you bring a dog, ensure it is well-behaved, on a leash when appropriate, and capable of handling the distance and conditions, perhaps in a bike trailer.
You'll experience breathtaking scenery through the Crete Senesi, known for its unique 'lunar landscape.' Expect expansive clay hills, picturesque valleys, isolated farmhouses, and dirt roads beautifully lined with cypress trees. The route offers a rich blend of vineyards, olive groves, charming small towns, and the quintessential cultural landscapes of Southern Tuscany.
Yes, the route passes through several small towns like Monteroni d'Arbia and Asciano, where you can find cafes, restaurants, and shops to refuel. It's always a good idea to carry sufficient water and snacks, especially on longer stretches between towns.