4.7
(157)
4,424
riders
4
rides
No traffic road cycling routes around Radicondoli traverse the undulating Sienese hills of Tuscany, offering varied gradients and panoramic views. The region is characterized by ancient forests of oak and chestnut, meadows, and a network of secondary roads with low traffic. Cyclists can explore diverse natural environments, including wide valleys and the northern foothills of the Maremma, providing a blend of challenging climbs and exhilarating descents.
Last updated: June 3, 2026
18
riders
54.2km
03:09
1,280m
1,280m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
15
riders
27.1km
01:32
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
10
riders
38.2km
02:03
770m
770m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
6
riders
14.1km
00:49
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
31.8km
01:35
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Radicondoli
An ancient castle located north of the Monterufoli Forest, Micciano stands out from its high reddish gabbro cliff called the 'Pinzo', which faces the hill on which the village of Libbiano stands, separated from the deep Adio Valley. Its name appears to derive from the Latin 'Fundus Mitianus or Maecianus', the name of a Roman legionary who, benefiting from the 'Julian Law', was gifted a large plot of land in that area in exchange for valorous military deeds. The oldest document of the small village's history, dating back to 947, is preserved in the Episcopal Curia of Volterra and refers to the investiture of Giovanni di Giovanni as parish priest, while a papal bull from Pope Alexius III, dated 1076, confirms the donation of Micciano and its court to the Abbey of Monteverdi by Emperor Henry II of Saxony.
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The Montesiepi Hermitage was built immediately after the saint's death, over the ancient hut where San Galgano lived during his last year (1181). The hermitage was consecrated in 1185 by the bishop of Volterra, Ildebrando Pannocchieschi. The small complex consists of the circular church interrupted only by the small apse, the chapel with frescoes by Lorenzetti, and the entrance porch. In the porch, look down to the left and look for an "original" medieval plaque that reminds the pilgrim... that he must die and that life is short. The original church was circular, then the entrance hall was added in 1200. The bell tower and Lorenzetti's chapel were added in the following century. The rectory dates back to the 18th century. The dome, constructed from alternating rows of white stones, is extremely elegant. Inside the Hermitage, in the center of the Rotonda, there is the famous Sword of San Galgano, stuck in the rock for over 800 years.
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Built in the 13th century in Gothic style and dedicated to the saint from Chiusdino, today it is completely in ruins: only the walls remain standing, with the apse still in evidence, perfectly facing east, while on the upper part of the facade there are two pointed windows. The roof of the Abbey of San Galgano is no longer there today. The "official" version says that it deteriorated and then fell over the centuries, while an alternative version, according to some legend and according to others truth, states that it was originally made of lead, and was sold by Girolamo Vitelli in 1550. Whatever the truth behind the roof of the abbey, after some restoration attempts that went badly, at the end of the 18th century it was deconsecrated and left to the elements until the present day. The ruins of the Abbey of San Galgano, with its profile still intact and immersed in the Tuscan countryside, offer a truly incredible and particular view. In addition to the roof, the floor is also missing, which during the summer turns into a grassy blanket, while you can still see a transept with three naves and 4 chapels with cross vaults. Next to the Abbey of San Galgano there is the cloister, which was rebuilt at the beginning of the last century, using the original materials. Some accessory rooms are also very beautiful, which can also be visited with the entrance ticket to the abbey, including the chapter house, where the monks originally met to deliberate the main rules of the community, and the scriptorium, which was the place where the monks copied the manuscripts.
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The origin of this small town is as a castle. Today only the imprint remains in the urban planning and in the strategic position: perched on a rocky spur between the Trossa and the Adio. Near Micciano, you will find spectacular hairpin bends, perfect for tackling by bike. Smooth climbs, adrenaline-filled descents and breathtaking views make this place a true gem for those who love cycling.
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Near Micciano, these hairpin bends are among the most fun you'll ever ride on a bike, both uphill and downhill. The easy slopes and the many panoramic points make this segment truly unique. The asphalt is also in good condition.
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Place of worship and prayer Sanctuary dedicated to San Galgano Guidotti, a 12th century knight, with his sword exposed as a sacred relic Strada Comunale di S. Galgano, 53012 Chiusdino SI 0577756700
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To see at least as much as the ruins of the church of San Galgano. The chapel is a little off the beaten track and freely accessible. Inside is a simple but beautiful dome and a mosaic ceiling in an adjoining room.
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There are 5 dedicated no-traffic road cycling routes around Radicondoli featured in this guide. These routes offer a mix of moderate and difficult options, ensuring varied experiences for cyclists.
The routes around Radicondoli traverse the classic undulating Tuscan hills, offering varied gradients. You can expect both challenging climbs and exhilarating descents. For instance, the Micciano Switchbacks – Borgo di Libbiano loop features over 1200 meters of elevation gain, while the Parish Church of Saint John the Baptist – Passo dell'Incrociati loop has over 600 meters.
The region's climate makes spring and autumn ideal for road cycling, offering pleasant temperatures and lush landscapes. Summer can be warm, but early morning rides are still enjoyable. Winter can be cooler, but many days remain suitable for cycling.
While most routes in this guide are rated moderate to difficult due to the hilly terrain, the focus on secondary roads with low traffic makes them safer for families with older, experienced children. The View of Pomerance – Poggio alle Forche loop is shorter, at just under 14 km, and could be a good option for those looking for a less strenuous ride.
Radicondoli is nestled within the Colline Metallifere, characterized by ancient forests and diverse flora. You can also explore unique geothermal phenomena. The Biancane Nature Park, for example, offers sights of steam columns and bubbling mud lagoons, providing a distinctive natural backdrop to your ride.
Many routes connect Radicondoli with other charming medieval villages. The Belforte loop from Frassini takes you past the preserved medieval layout of Belforte. The region is also close to the impressive Abbey of San Galgano, a significant historical site worth visiting. Radicondoli itself is a well-preserved medieval village.
Yes, all 5 routes featured in this guide are designed as loop routes, allowing you to start and finish at the same point. This makes planning your ride and return journey straightforward.
Many of these routes start from or pass through small towns and villages like Pievescola, Pomarance, or Montalcinello, where public parking is generally available. It's advisable to check local parking regulations upon arrival, especially in smaller village centers.
The routes are specifically curated to utilize secondary roads and quiet country lanes that see very little vehicular traffic. This ensures a more peaceful and safer cycling experience, allowing you to fully immerse yourself in the Tuscan landscape without constant interruption from cars.
The area is highly rated by the komoot community, with an average score of 4.7 stars from over 150 ratings. Reviewers often praise the stunning panoramic views of the Tuscan countryside, the challenging yet rewarding climbs, and the tranquility of the low-traffic roads that allow for an immersive cycling experience.
Yes, for experienced cyclists seeking a challenge, the Micciano Switchbacks – Borgo di Libbiano loop from Riserva Naturale Foresta di Berignone is rated as 'difficult'. This route covers over 53 km with more than 1200 meters of elevation gain, providing a demanding yet rewarding ride through the Sienese hills.
Many routes pass through or near charming medieval villages such as Radicondoli, Chiusdino, or Monticiano. These villages typically offer cafes, bars, and small shops where you can stop for refreshments, a coffee, or a meal. The Mao Bar loop from Montalcinello, for example, starts and ends in a village likely to have amenities.


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