4.3
(126)
1,542
riders
188
rides
Gravel bike trails Civitella In Val Di Chiana traverse a diverse landscape within the Val di Chiana Aretina region of Tuscany. The area features rolling hills, ancient woodlands, and the iconic "Strade Bianche" (white gravel roads) that define Tuscan cycling. This terrain offers a mix of challenging climbs and scenic descents, providing varied experiences for gravel bikers. The region's natural beauty is shaped by its historical connection to the Chiana River and extensive reclamation work.
Last updated: July 5, 2026
4.5
(2)
25
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.0
(2)
32
riders
81.2km
05:28
1,000m
1,000m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4.5
(2)
25
riders
53.7km
03:40
840m
840m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
14
riders
34.1km
02:25
60m
60m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
23
riders
55.8km
04:04
990m
990m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Historic work of hydraulic engineering from the 12th century. Starting point of the suggestive Sentiero della Bonifica (Reclamation Trail) and junction with the Ciclopista dell'Arno (Arno Cycle Path).
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pretty here, very pretty
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Montecchio Vesponi Castle dominates the Val di Chio from a hill over 360 meters above sea level. With its crenellated walls, towers, and an imposing 30-meter-high square tower, it is one of the best-preserved medieval castles in Tuscany and can be recognized from afar throughout the valley. Contested for centuries by Arezzo and Florence for its strategic position on the road to Cortona, it became a Florentine stronghold after the Battle of Campaldino in 1289. In the 14th century, it was also home to the famous mercenary captain John Hawkwood. Today, the castle comes back to life with guided tours, events, and reenactments that evoke the atmosphere of the Middle Ages.
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In Castiglion Fiorentino, just outside the city walls, stands the Church of the Madonna della Consolazione. Its history stems from a sacred image of the Madonna and Child, attributed to Luca Signorelli, once kept in a tabernacle along the road. Tradition holds that Eleonora di Toledo, wife of Cosimo I de' Medici, regained her sight by praying before that image. In gratitude, she financed the construction of the church, which began in 1565 and was completed only decades later. Inside, in a side chapel, the original fresco of the Madonna is still preserved.
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A panoramic spot from which to observe the entire Valdichiana.
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A castle immersed in a forest, with an unmistakable tower visible from various points and with a wide view of the Valdichiana up to Arezzo and the Apennines.
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A curious stop even if you're not a true Aretino: read the story and refresh yourself at the always-open fountain.
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In the summer an early start or cycling on a cooler day is advisable, as the trail does not provide much shadow
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There are over 160 gravel bike trails around Civitella In Val Di Chiana, offering a wide range of options for different skill levels and preferences. The komoot community has rated these routes with an average score of 4.2 stars.
The region is characterized by diverse terrain, including rolling hills, ancient woodlands, and the famous 'Strade Bianche' (white gravel roads) that are a hallmark of Tuscan cycling. You'll find a mix of challenging climbs and scenic descents, winding through vineyards, olive groves, and cypress-lined paths.
Yes, the gravel biking network around Civitella In Val Di Chiana caters to various abilities. While many routes are considered difficult, there are also over 30 moderate and a few easy trails available, ensuring options for beginners and experienced riders alike.
Many routes pass through or near historical points of interest. For example, the Gargonza Water Fountain – Gargonza Castle loop from Montagnano leads past the historic Gargonza Castle. Other trails might bring you close to the medieval village of Civitella itself, or the Romanesque bridge Ponte Buriano.
Absolutely. The Chiusa dei Monaci – Monks' Lock loop from Riserva naturale Ponte a Buriano e Penna explores areas near the Ponte a Buriano e Penna Nature Reserve, offering varied natural scenery. You can also find shaded rides through ancient forests, especially around Borgo Sant'Ercolano, and sections along the Canale Maestro della Chiana.
The area is highly rated by the komoot community, with an average score of 4.2 stars from over 100 reviews. Riders frequently praise the stunning panoramic views, the unique experience of riding on the 'Strade Bianche,' and the opportunity to combine challenging rides with visits to charming medieval villages and local culinary delights.
Yes, many of the gravel bike routes in the region are designed as loops, allowing you to start and finish at the same point. Examples include the Montecchio Castle – Bonifica Trail loop from Pieve al Toppo and the Bonifica Trail – Reclamation Trail loop from Via Chiari.
While specific parking areas for gravel bikers are not explicitly designated, you can typically find parking in and around the starting points of many routes, particularly in the villages and towns like Civitella, Pieve al Toppo, or Montagnano. Always check local signage for parking regulations.
Public transport options to reach the starting points of gravel trails in the Val di Chiana region can be limited. It's advisable to research local bus services or regional trains to nearby towns like Arezzo, and then plan your route or consider a short transfer to your desired starting point. Bringing your bike on public transport may have restrictions.
Yes, the Val di Chiana is known for its culinary traditions. Many routes pass through or near small villages where you can find cafes for a perfect coffee, or trattorias offering excellent local food and wine. Civitella itself, and other charming medieval towns, provide ample opportunities to refuel and experience 'la dolce vita'.
While many routes are challenging, there are easier sections and trails suitable for families. The Canale Maestro della Chiana, for instance, offers flatter, more accessible paths like the Sentiero della Bonifica, which are great for relaxed biking with children. Look for routes categorized as 'easy' on komoot for the most suitable options.
Spring (April-May) and Autumn (September-October) are generally considered the best times for gravel biking in Tuscany. The weather is milder, the landscapes are vibrant, and the heat of summer is avoided. This allows for more comfortable riding conditions and better enjoyment of the scenic routes.


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