The best cycling routes in Siena
4.5
(5405)
67,422
riders
2,217
rides
Touring cycling in Siena offers diverse landscapes characterized by rolling hills, expansive vineyards, and olive groves. The region features unpaved gravel roads known as "strade bianche," which provide a challenging experience. Key natural features include the impressionistic landscapes of Crete Senesi and the UNESCO World Heritage site of Val d'Orcia. The terrain presents gentle climbs and descents in areas like Val d'Arbia, alongside more significant elevation gains in others.
Best touring cycling routes in Siena
- The most popular touring cycling…
Last updated: May 2, 2026
4.7
(40)
206
riders
24.6km
02:02
470m
470m
This difficult 15.3-mile touring cycling loop through Val d'Orcia connects Pienza and San Quirico d'Orcia, featuring rolling hills and grave
4.8
(8)
218
riders
68.3km
04:41
1,140m
1,140m
Cycle the difficult 42.5-mile L'Eroica Chianti Loop from Siena, featuring white gravel roads, vineyards, and Tuscan scenery.
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4.8
(14)
2,774
riders
48.1km
03:20
460m
460m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.6
(13)
202
riders
71.6km
04:45
940m
940m
This difficult 44.5-mile touring bicycle loop from Siena to Asciano offers challenging climbs and stunning views of the Crete Senesi.
4.7
(15)
181
riders
58.2km
03:58
770m
770m
Cycle the Strade Bianche Siena Loop, a difficult 36.2-mile touring route through Tuscany's iconic white gravel roads and rolling hills.
4.3
(28)
136
riders
37.5km
02:48
730m
730m
Hard bike ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.4
(23)
195
riders
35.2km
03:11
710m
710m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.2
(27)
104
riders
27.2km
02:14
490m
490m
Hard bike ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.5
(19)
148
riders
53.1km
03:42
670m
670m
This difficult 33.0-mile touring cycling route from Siena to Gracciano d'Elsa explores Tuscan landscapes and the medieval town of Monteriggi
4.9
(7)
2,193
riders
50.8km
03:24
790m
790m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Tips from the Community
The Cippo is located at the entrance of the Strada Bianca on the SP99 side
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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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The area is stunning, and the views of the hills are fantastic. Meadows alternate with clayey areas, cracks in the ground, and rows of trees offer breathtaking views that are even more beautiful and fiery at sunset. You can leisurely stroll along the beautiful roads, enjoying the scenery.
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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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Small village with an excellent refreshment point
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Frequently Asked Questions
How many touring cycling routes are available in Siena?
Siena offers a vast network of touring cycling routes, with over 2,200 options available. These routes cater to various skill levels, from easy rides to more challenging circuits across the region's diverse landscapes.
What kind of terrain can I expect on Siena's touring cycling routes?
The terrain in Siena is characterized by iconic Tuscan scenery, including rolling hills, expansive vineyards, and olive groves. You'll encounter both paved roads and the famous unpaved gravel roads known as "strade bianche." While some areas like Val d'Arbia offer gentle climbs and descents, many routes feature significant elevation gains, particularly in regions like Chianti and Val d'Orcia.
Are there any family-friendly touring cycling routes in Siena?
Yes, Siena offers options for various ability levels, including over 130 easy touring cycling routes. While many routes feature elevation gains, you can find more relaxed rides suitable for families. For example, some sections of the ancient pilgrimage routes like the Via Francigena can be adapted for easier cycling.
Can I find circular touring cycling routes around Siena?
Absolutely. Many touring cycling routes in Siena are designed as loops or round trips, allowing you to start and end in the same location. An example is the From Buonconvento to Montalcino — Round trip, which offers a scenic journey through the region.
What historical sites or natural features can I explore along the touring cycling routes in Siena?
Siena's cycling routes are rich with historical and natural attractions. You can pass through ancient city gates like Porta Romana, explore medieval villages such as Murlo, or visit impressive abbeys like the Certosa di Maggiano. Natural highlights include the impressionistic landscapes of Crete Senesi and the UNESCO World Heritage site of Val d'Orcia. Don't miss the chance to see landmarks like the town of Pienza or the Radicofani Fortress.
Are there touring cycling routes that pass through vineyards or offer wine-tasting opportunities?
Yes, the Siena region is world-renowned for its wines. Routes often traverse the famous Chianti and Brunello regions, offering opportunities to cycle past extensive vineyards and olive groves. The L'Eroica Chianti Loop from Siena is a prime example, exploring the heart of the Chianti region where you can find numerous wine estates and cellars for tastings.
What are the "strade bianche" and are there touring cycling routes that feature them?
The "strade bianche" (white roads) are unpaved gravel roads that are a signature feature of Siena's cycling landscape, even hosting a key stage of the UCI WorldTour. These roads offer a challenging yet picturesque experience. You can definitely find routes that incorporate them, such as the Strade Bianche Siena Loop, which allows you to experience these unique surfaces.
When is the best time of year for touring cycling in Siena?
Spring (April-May) and autumn (September-October) are generally considered the best times for touring cycling in Siena. During these seasons, the weather is typically mild and pleasant, and the landscapes are particularly vibrant, with blooming poppies in spring or rich autumnal colors. Summer can be very hot, while winter can be cooler and wetter.
What do other touring cyclists enjoy most about cycling in Siena?
The touring cycling routes in Siena are highly rated by the komoot community, with an average score of 4.5 stars from over 5,300 reviews. Cyclists often praise the stunning Tuscan scenery, the unique challenge of the "strade bianche," and the opportunity to explore charming medieval villages and historical sites along the way. The diverse landscapes, from the rolling hills of Chianti to the impressionistic views of Crete Senesi, are frequently highlighted.
Are there any less crowded touring cycling routes near Siena?
While popular areas like Chianti and Val d'Orcia can attract many cyclists, Siena's extensive network of routes means you can often find quieter paths. Exploring areas like Val d'Arbia, known for its gentle climbs, or seeking out less-trafficked sections of the ancient Via Francigena, can offer a more serene cycling experience away from the main tourist trails. The Francigena Cycle Route: Siena to Monteriggioni offers a historical journey that can provide a different pace.
Are there routes that connect Siena to other notable towns?
Yes, Siena serves as an excellent starting point for touring cycling adventures to other charming Tuscan towns. For instance, the From Colle Val d’Elsa to San Gimignano route allows you to explore beyond Siena's immediate vicinity, connecting you to other historical gems in the region.
What are some of the longer, more challenging touring cycling routes in Siena?
For experienced cyclists seeking a challenge, Siena offers numerous difficult routes with significant elevation gains. The Siena and Strade Bianche Loop, covering over 59 km with more than 1000 meters of elevation gain, is a great option. Another challenging route is the Crete Senesi – Radi Village loop from Monteroni Sud, which takes you through unique landscapes over a substantial distance.
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