4.5
(174)
2,273
riders
104
rides
Touring cycling around Asciano is characterized by rolling hills and distinctive clay-rich soil, forming the unique "lunar" appearance of the Crete Senesi region. The landscape also features classic Tuscan vineyard scenery and views of the Val d'Orcia. Many routes incorporate segments of the unpaved "strade bianche," known from professional cycling races. This area provides a varied terrain for touring cyclists, ranging from gentle slopes to challenging ascents.
Last updated: May 1, 2026
4.3
(13)
53
riders
31.9km
02:27
390m
390m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.8
(11)
81
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(6)
91
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.6
(5)
78
riders
66.7km
04:30
1,110m
1,110m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(3)
70
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Porta Romana is one of the ancient gates in the walls of Siena, located on the route of the ancient Via Cassia. It was built in 1327 - 1328 by Agnolo di Ventura and Agostino di Giovanni, equipped with battlements and a defensive wall. In 1417, Taddeo di Bartolo was commissioned to paint the fresco that was to adorn it with a depiction of the Virgin, like the other city gates, to implore divine protection for the city. In 1978, the frescoes, due to advanced deterioration, were detached and transferred to the Basilica of San Francesco. However, there is a Roman inscription at the Porta Romana!The inscription was written on a travertine tablet and, based on its graphic characters and content, can be dated to the Augustan period (27 BC – 0) saying "Silvanus sacr(um) / C. Victricius / Memor VIvir / [a] ugustalis posuit" = Caio Victricio Memore Seviro augustale dedicated a small temple to Silvanus.
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In Siena, as we know, your eye always falls there, on the shell-shaped Campo or the striped marble of the Duomo. And rightly so. But then there are those places that speak to you in a different voice, more raspy and sincere. Porta Romana is one of them. Let's be clear: this isn't a small archway placed there for show. This is a beast of brick and stone, a fortress planted to the south to tell those arriving from Rome: "Be careful, you're entering Siena." It's massive, imposing, it makes you feel small and immediately reminds you that this city was once a serious thing, a power that had to be defended. It has none of the frills of other monuments; it gets straight to the point, and for me, its charm begins right there.
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Very cool place for water refilling. Nice artwork.
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This beautiful Abbey can be visited inside by paying a ticket of 4 euros.
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Not only the Via Francigena passes here, but also the l'Eroica, a cycling event on vintage bicycles. More than just a race, it's a celebration of the golden age of cycling, a journey back in time, and a chance to discover the beautiful landscapes and cultural heritage of Tuscany.
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There are over 100 touring cycling routes around Asciano, catering to various skill levels. This includes 5 easy, 37 moderate, and 59 difficult routes, ensuring options for every cyclist.
Cycling around Asciano offers diverse and picturesque landscapes. You'll primarily experience the unique 'lunar' appearance of the Crete Senesi with its rolling, treeless hills and distinctive clay-rich soil. Additionally, routes often pass through classic Tuscan vineyard landscapes and provide views of the stunning Val d'Orcia.
Yes, many routes around Asciano are circular. For example, the moderate Asciano and the Francigena Way - Ring tour is a popular circular option exploring a section of the historic Francigena Way. Another challenging circular route is the View of the Crete Senesi – Beautiful scenic viewpoint loop from Asciano M. Oliveto M..
The 'strade bianche' are unpaved gravel roads famous from professional cycling races like L'Eroica and Strade Bianche. Many touring cycling routes around Asciano incorporate segments of these iconic white roads, offering a unique challenge and a taste of cycling history. They are a defining feature of the region's cycling experience.
The region is rich in cultural and natural highlights. You can encounter unique art installations like the Site Transitoire, historic structures such as Torre del Mangia in Siena, or charming villages like Buonconvento. The historic center of Asciano itself is a great stop, and the Siena Cathedral (Duomo di Siena) is also accessible on longer routes.
While many routes in Asciano feature rolling hills and 'strade bianche' which can be challenging, there are some easier options. There are 5 easy routes available, which are generally shorter and have less elevation gain, making them more suitable for families or beginners. Always check the route details for distance and elevation before heading out.
The touring cycling routes in Asciano are highly rated by the komoot community, with an average score of 4.5 stars from over 150 reviews. Cyclists often praise the stunning and unique landscapes of the Crete Senesi, the challenge of the 'strade bianche', and the opportunity to explore historic towns and vineyards.
Asciano offers beautiful cycling conditions throughout much of the year. Spring and autumn are generally considered ideal, with pleasant temperatures and vibrant landscapes. Summer can be hot, but early morning rides are still enjoyable. The landscape transforms with the seasons, offering different visual experiences from beige to burnt sienna.
Yes, e-bike tours are readily available in the Asciano region. They provide an excellent way to comfortably explore the rolling hills and challenging terrain of the Crete Senesi, allowing cyclists of all fitness levels to enjoy the scenic beauty. For more information on e-bike tours, you can check resources like visittuscany.com.
Yes, several routes incorporate the historic center of Asciano. For instance, the difficult Beautiful scenic viewpoint – Historic center of Asciano loop from Asciano M. Oliveto M. offers scenic viewpoints and takes you right through the town, which is a convenient stop for a coffee or a break.
Absolutely. For experienced cyclists seeking a challenge, there are 59 difficult routes available. These often feature significant elevation gain and longer distances. An example is the challenging Torre del Mangia – Porta Romana (Siena) loop from Trequanda, which covers over 67 km and includes substantial climbing.
Route durations vary significantly based on distance and difficulty. Moderate routes like the Asciano and the Francigena Way - Ring tour typically take around 2 hours 27 minutes. More challenging and longer routes, such as the Buonconvento – Beautiful scenic viewpoint loop from Trequanda, can take over 4 hours to complete.


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