4.4
(1764)
19,323
riders
790
rides
Gravel biking in Siena is characterized by its iconic "Strade Bianche" (white roads), unpaved gravel paths that traverse the region's diverse terrain. The landscape features rolling hills, extensive vineyards, and olive groves, particularly in areas like the Val d'Orcia and Crete Senesi. This region offers a continuous mix of ascents and descents, combining both paved and unpaved surfaces. The terrain provides varied challenges suitable for different fitness levels.
Last updated: May 10, 2026
4.9
(50)
532
riders
52.8km
04:20
870m
870m
Hard gravel ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.7
(33)
260
riders
47.6km
03:45
730m
720m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4.3
(10)
99
riders
62.4km
04:26
860m
850m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
70.0km
07:13
1,660m
1,660m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.9
(25)
377
riders
124km
10:18
2,560m
2,560m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.7
(28)
358
riders
69.3km
04:58
1,390m
1,390m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.9
(44)
519
riders
60.7km
04:12
1,150m
1,150m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(25)
701
riders
104km
06:42
1,510m
1,510m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.9
(18)
435
riders
140km
09:37
1,840m
1,840m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(6)
710
riders
110km
06:58
1,660m
1,660m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Really beautiful loop tour, given the places it's hard not to be, but unfortunately we discovered that the track leads onto an impassable private property, please check where it stops to turn back! "Adventurous" alternative. Everything else magnificent! Staggia, Monteriggioni, the farms all very characteristic.
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The San Martino in Grania sector is one of the longest (approx. 9.5 km) and most challenging gravel sections of the Strade Bianche. Located between km 69.5 and 78.8 of the route, it offers a breathtaking Tuscan landscape with continuous ups and downs and gradients exceeding 12%. It is a technical and crucial point before Monte Sante Marie.
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Beautiful panoramic view of Siena!
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You can't not do it!!
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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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Vagliagli is a hamlet in the municipality of Castelnuovo Berardenga, in the province of Siena. An ancient 13th-century village, it is located at 511 meters above sea level, along the provincial road leading to Radda in Chianti.
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Siena offers a vast network of nearly 900 gravel bike trails. These routes traverse diverse landscapes, from the iconic Strade Bianche to the rolling hills of Val d'Orcia and the unique lunar landscape of the Crete Senesi.
Siena's gravel trails are characterized by continuous 'up and down' sections, featuring a mix of paved and unpaved roads. You'll encounter the famous 'Strade Bianche' (white gravel roads), along with varied terrain including vineyards, olive groves, and the distinctive clay formations of the Crete Senesi. The region offers challenges suitable for various fitness levels.
While many routes in Siena are considered difficult, there are 16 routes classified as easy and 196 as moderate, providing options for beginners or those seeking a less strenuous ride. These routes still offer the beautiful Tuscan scenery without the most demanding climbs.
Siena's gravel trails pass through a wealth of historical and natural attractions. You can explore medieval villages like Pienza and Montalcino, or discover historical sites such as the Radicofani Fortress and Monte Sante Marie Gravel Road. Natural highlights include the unique 'lunar' landscape of the Crete Senesi and the picturesque Val d'Orcia. You might also encounter thermal springs like Bagno Vignoni for a relaxing stop.
Yes, many gravel routes in Siena are designed as loops, allowing you to start and end in the same location. An example is the challenging Val d'Elsa Loop from Casole d'Elsa, which covers over 70 km. Another option is the Pienza – Via Francigena Gravel Route loop from Buonconvento, offering a longer, immersive experience.
The best time for gravel biking in Siena is typically spring (April-May) and autumn (September-October). During these seasons, the weather is milder, and the landscapes are particularly vibrant with blooming wildflowers or rich autumn colors. Summer can be very hot, and winter may bring colder, wetter conditions, making some gravel sections muddy.
Absolutely. Many routes in Siena wind through the region's famous vineyards, especially in areas like Montalcino, known for Brunello wine, and the Chianti hills. You'll often find charming medieval villages along the way, such as Pienza or Montalcino, which offer opportunities to sample local delicacies like Pecorino cheese or enjoy a meal. The View of Vagliagli – Radda in Chianti loop from Villa a Sesta is a great example of a route through wine country.
Yes, Siena's gravel biking scene is deeply connected to these historic paths. You can ride sections of the L'Eroica vintage bike course, such as the popular On the trail of the Eroica in the hills of Chianti. The ancient pilgrimage route, Via Francigena, also forms part of several gravel itineraries, offering a unique historical cycling experience, like the Pienza – Via Francigena Gravel Route loop from Buonconvento.
The gravel trails in Siena are highly regarded by the komoot community, with an average rating of 4.4 stars from over 1,700 reviews. Riders frequently praise the stunning Tuscan panoramas, the unique challenge of the Strade Bianche, and the opportunity to discover charming medieval villages and historical sites along the routes.
Siena is well-known for its challenging gravel routes. With 683 routes classified as difficult, experienced riders will find plenty to test their skills. Routes like The Classic of Classics from Siena or the extensive Brolio Castle – Crete Senesi loop from San Regolo offer significant elevation gains and long distances, providing a rewarding experience for advanced gravel bikers.
Many gravel routes in Siena are accessible from towns and villages that have public transport connections, making it possible to reach starting points without a car. For those driving, parking is generally available in the larger towns and villages that serve as common starting points for rides, such as Siena itself, Buonconvento, or Casole d'Elsa. It's advisable to check specific parking options for your chosen starting location.
Yes, Siena's hilly terrain provides numerous opportunities for breathtaking panoramic views. Routes often climb to elevated points offering expansive vistas of the Val d'Orcia, the Crete Senesi, and the surrounding vineyards. The Poggio Montecercone viewpoint is a notable spot, and many trails are designed to maximize scenic overlooks, allowing you to fully appreciate the iconic Tuscan landscape.


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