4.6
(721)
31,706
riders
4
rides
Road cycling around Asciano is characterized by the distinctive rolling clay hills of the Crete Senesi, a region known for its unique "moonscape" terrain. The area features well-paved surfaces and offers routes with significant elevation gains, often winding through iconic cypress trees and picturesque landscapes. It serves as a gateway to the Val d'Orcia, a UNESCO World Heritage site, providing a harmonious blend of natural beauty and human influence. The terrain is diverse, catering to various cycling preferences with options…
Last updated: May 19, 2026
4.0
(7)
95
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.2
(5)
32
riders
26.6km
01:18
400m
400m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
17
riders
35.0km
02:01
680m
680m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
10
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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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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Added to the collection: https://www.komoot.com/de-de/collection/3600632/-naturdenkmaeler-besondere-baeume-und-weitere-schaetze-der-natur
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The famous Strade Bianche route is a fascinating itinerary that moves on the winding dirt roads with more or less steep climbs. Each stretch of dirt road is identified with a travertine stone like the one you can find here. It is the proof that you are traveling the Strade Bianche near Colle Pinzuto.
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The name is due to the bridge that crosses the Arbia stream. The place has been documented since the early Middle Ages as it lies along the route of the ancient Via Francigena. Particularly in the itinerary of Sigeric, Archbishop of Canterbury, the place represented the fourteenth stage (Submansio) and was then called Arbia. The bridge that gives its name to the city was built by the municipality of Siena in 1388 and rebuilt in 1656 under Prince Mattia de' Medici, governor of Siena.
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There are 7 carefully curated no-traffic road cycling routes around Asciano, all offering a moderate challenge suitable for experienced riders looking for quiet, scenic paths.
The routes primarily feature well-paved surfaces, but some may include short, unpaved segments, characteristic of the famous 'Strade Bianche' of the Crete Senesi. You'll encounter rolling hills and significant elevation gains, offering a varied and engaging cycling experience.
Yes, routes like the Tarmac SP111 – Short Gravel Section loop from Monteaperti incorporate short gravel sections, providing a taste of the iconic 'Strade Bianche' while keeping the focus on road cycling.
The Crete Senesi transforms with the seasons. Spring and autumn generally offer the most pleasant temperatures and stunning landscapes, from vibrant green fields to golden and ochre hues. Summers can be hot, while winters are cooler but still offer unique beauty.
You'll cycle through the distinctive rolling clay hills of the Crete Senesi, often dotted with iconic cypress trees. Many routes offer panoramic views of this 'otherworldly moonscape.' Keep an eye out for the Site Transitoire, an art installation designed for contemplation of the landscape, and the symbolic Desert of Accona.
Absolutely. The region is rich in history. You might pass by charming villages like San Giovanni d'Asso Historic Village or the medieval Bibbiano Castle. The historic center of Asciano itself, with its medieval walls and architectural gems, is also worth exploring.
The komoot community highly rates the cycling experience around Asciano, with an average score of 4.3 stars from 80 ratings. Reviewers often praise the stunning, unique landscapes of the Crete Senesi, the tranquility of the routes, and the rewarding challenge of the rolling hills.
Yes, many of the routes are designed as loops, allowing you to start and finish in the same location. For example, the Grancia di Cuna – San Fabiano Countryside View loop from Siena Zona Industriale offers a substantial circular ride through the countryside.
Asciano town center offers various parking options. For routes starting slightly outside the town, consider parking near local train stations or designated village parking areas, which are generally less crowded and provide good access to the quieter roads.
Asciano has a train station, making it accessible by regional train services. From Asciano, you can often cycle directly onto the quieter roads. For specific route starting points further afield, local bus services might be an option, though their frequency can vary.
Absolutely. The region is famous for its iconic cypress trees. The Cypress-lined avenue in Montechiaro – Colle Pinzuto loop from Castelnuovo Berardenga is a great example, taking you past picturesque, tree-lined roads that define the Tuscan landscape.
All 7 of the no-traffic road cycling routes around Asciano are rated as 'moderate' difficulty. They involve significant elevation changes and distances, making them suitable for cyclists with a good level of fitness looking for a rewarding challenge.


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