4.5
(165)
4,406
riders
3
rides
Road cycling around Radicofani offers routes through the heart of Tuscany's Val d'Orcia, characterized by rolling hills, picturesque cypress trees, and expansive fields. The region is situated on an ancient volcanic cliff, providing views of the surrounding Val d'Orcia and the Crete Senesi. The landscape also features unique rock formations known as *calanchi* and *biancane*, with many routes offering well-paved surfaces and manageable gradients.
Last updated: May 2, 2026
27
riders
29.5km
01:44
700m
700m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
13
riders
32.0km
02:04
940m
940m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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5
riders
14.6km
00:51
350m
350m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Radicofani
Overlooking Piazza Grande, the Palazzo Comunale is one of Montepulciano's symbolic buildings. Originally from the 13th century and reworked by Michelozzo in the 15th century, it echoes the forms of Florence's Palazzo della Signoria, desired by Cosimo I. From the visitable tower, a breathtaking panorama opens up.
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to visit without ifs or buts, nice climb to reach it
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village with a nice climb and much less chaotic, 10/10 view!
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The similarities between the Palazzo Comunale of Montepulciano and the Palazzo della Signoria of Florence are striking, but this is not historical plagiarism, but rather a personal request by Cosimo I de' Medici.
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The Cathedral of the Assumption in Montepulciano is truly a Renaissance jewel set in a beautiful square, Piazza Grande.
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There are 4 dedicated no traffic road cycling routes detailed in this guide, ranging from moderate to difficult. These routes allow you to experience the stunning Val d'Orcia landscape with minimal vehicle interference.
The routes primarily feature well-paved surfaces winding through the iconic rolling hills of Tuscany. While most roads are smooth, some sections might include unpaved stretches, characteristic of the region's rural charm. Expect manageable gradients that offer a rewarding challenge without overly steep climbs.
Yes, for those seeking a challenge, the Monte Amiata summit loop from La Liccia is classified as difficult, featuring significant elevation gain over its 32-kilometer distance. This route offers a demanding ride with spectacular views.
The region is rich in scenic viewpoints and historical landmarks. Many routes offer panoramic views of the Val d'Orcia, the Crete Senesi, and Monte Amiata. You can also spot the majestic Radicofani Fortress, which offers extraordinary 360-degree views from its tower. Other points of interest include the historic Posta Medicea and various charming churches. For specific natural features, the unique *calanchi* and *biancane* rock formations provide a different, almost lunar appearance to the landscape.
Yes, all the routes listed in this guide are circular, designed to bring you back to your starting point. For example, the View of Val d'Orcia – Spedaletto Castle loop from Pienza offers a 57.7 km circular ride through picturesque landscapes.
The region is beautiful year-round, but spring (April-May) and autumn (September-October) are ideal. During these seasons, the weather is mild, and the landscapes are particularly vibrant—green in spring and golden in autumn. Summer can be hot, but early morning rides are still enjoyable. Winter offers a quieter experience, though some services might be limited.
The area is highly rated by the komoot community, with an average score of 4.46 stars from 112 ratings. Reviewers often praise the breathtaking Tuscan scenery, the quiet, well-maintained roads perfect for road cycling, and the rewarding climbs that offer stunning panoramic views of the Val d'Orcia.
While all routes require a certain level of fitness due to elevation changes, the View of Pienza – Monticchiello loop from I Poggiardelli is the shortest at 14.6 kilometers with moderate difficulty, making it a more accessible option for families with older children or those looking for a less strenuous ride.
Radicofani and nearby villages like Pienza and L'Olmo, which serve as starting points for many routes, typically offer public parking areas. It's advisable to check local signage upon arrival for specific parking regulations and availability, especially during peak season.
Beyond the classic Tuscan vistas, the region boasts unique natural features. You can find thermal waters in nearby Bagno Vignoni and Bagni San Filippo, known for their therapeutic properties. Additionally, the area around Radicofani features several caves, such as the Grotta di San Filippo Benizi and the Grotta del Bruco, offering a different kind of exploration. For more information on the landscape, you can visit visitvaldorcia.it.
Public transport options to Radicofani are limited, and bringing bikes on regional buses or trains can be challenging. It's generally recommended to travel by car to the area, especially if you plan to bring your own road bike. Some local services might accommodate bikes, but it's best to confirm directly with the transport provider beforehand.
Yes, the charming villages and towns along these routes, such as Radicofani itself, Pienza, and Montepulciano, offer various cafes, trattorias, and restaurants where you can refuel and enjoy local Tuscan cuisine. These spots are perfect for a mid-ride break or a post-ride meal.


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