4.4
(211)
5,998
riders
3
rides
No traffic road cycling routes around Rapolano Terme traverse a landscape characterized by rolling clay hills, extensive vineyards, and picturesque olive groves. The region is situated within the Crete Senesi, featuring distinctive white clay hills and deep gullies. The terrain includes both paved roads and "strade bianche" (white roads), offering diverse surfaces for cycling. The Ombrone River also winds through the territory, adding to the natural beauty.
Last updated: July 9, 2026
4.7
(3)
94
riders
95.0km
04:28
1,100m
1,100m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
16
riders
35.1km
02:02
690m
690m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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14
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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Beautiful village located on top of one of the hills between Valdambra and Valdichiana, beautiful climb from both sides
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The main street of the town with many restaurants and bars with the beautiful view of the historic amphitheater
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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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Komoot currently features 3 dedicated no-traffic road cycling routes around Rapolano Terme. These routes are carefully selected to offer serene rides away from busy roads, allowing you to fully immerse yourself in the Tuscan landscape.
The no-traffic road cycling routes around Rapolano Terme traverse the iconic Crete Senesi, characterized by rolling clay hills, extensive vineyards, and picturesque olive groves. While the focus is on paved roads, you might encounter some sections of the famous 'strade bianche' (white roads), particularly if you venture onto routes like the Monte Sante Marie Gravel Road or the Strade Bianche – San Martino in Grania to Monteroni d'Arbia, which are part of the region's cycling heritage.
Yes, for experienced riders seeking a challenge, the Monte San Savino Old Town – Colonna del Grillo loop from Lucignano-Marciano-Pozzo is a difficult route spanning over 95 km with more than 1100 meters of elevation gain. This route offers a demanding yet rewarding experience through the region's stunning scenery.
These routes offer a wealth of sights. You'll cycle through the breathtaking landscapes of the Crete Senesi, with expansive views over the iconic clay-hill terrain. Points of interest include historical villages like Asciano Historic Center, and unique landmarks such as the Site Transitoire, a panoramic viewpoint. The routes also pass near charming castles like Gargonza Castle and historical settlements like Scrofiano.
Absolutely. For a moderate ride, consider the Porta Romana (Siena) – Torre del Mangia loop from Castelnuovo Berardenga, which is about 35 km long with around 690 meters of elevation. Another excellent moderate option is the View of the Tuscan Countryside – Colle Pinzuto loop from Castelnuovo Berardenga, covering approximately 33 km with over 600 meters of climbing, offering beautiful vistas without extreme difficulty.
Rapolano Terme benefits from a climate that allows for cycling almost year-round. However, the spring (April-May) and autumn (September-October) months are particularly ideal. During these seasons, the weather is pleasant, the landscapes are vibrant, and the thermal waters are especially inviting after a ride. Summers can be hot, so early morning or late afternoon rides are recommended.
Yes, all the no-traffic road cycling routes featured in this guide are circular loops, designed for convenience. This means you can start and end your ride at the same point, making logistics simpler for your cycling adventure around Rapolano Terme.
The area is highly rated by the komoot community, with an average score of 4.4 out of 5 stars from over 160 reviews. Cyclists often praise the stunning, diverse landscapes of the Crete Senesi, the quiet roads that allow for peaceful rides, and the rich historical and cultural points of interest encountered along the way.
Rapolano Terme is renowned for its thermal waters. The Terme dell'Antica Querciolaia and Terme di San Giovanni are prominent thermal spas in the area, offering excellent opportunities for relaxation and recovery after your ride. These spas have been cherished since Etruscan times for their beneficial properties.
Given that many of these routes start from towns or villages like Castelnuovo Berardenga or Lucignano-Marciano-Pozzo, you can typically find public parking facilities within these settlements. It's advisable to check local parking regulations upon arrival, especially in smaller historic centers.
The routes often pass through or near charming Tuscan villages and towns. These locations usually offer cafes, trattorias, and small shops where you can stop for refreshments, a coffee, or a traditional meal. Planning your stops in advance can enhance your cycling experience.
Beyond the iconic clay hills of the Crete Senesi, you'll experience landscapes dotted with olive-covered hills and patches of Turkey and sessile oaks. The region is also shaped by ancient travertine quarries, which have contributed to its unique architectural style, and the Ombrone River winds through the territory, adding to the natural beauty.


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