4.6
(97)
767
riders
54
rides
Gravel biking around Cortona is characterized by rolling hills, extensive vineyards, and olive groves, offering varied terrain for cyclists. The region overlooks the Valdichiana plain and features views of Lake Trasimeno. Ancient Etruscan and Roman walls surround the town, providing historical context to the landscape. The area's elevation, approximately 500-600 meters above sea level, contributes to panoramic vistas.
Last updated: May 19, 2026
32
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
12
riders
86.3km
06:06
1,040m
1,040m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
12
riders
69.5km
04:58
980m
980m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.5
(2)
11
riders
47.4km
03:03
430m
430m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
10
riders
69.4km
04:49
980m
980m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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I walked the stretch from Borghetto to Castiglione del Lago (8/9 km) and was a little disappointed that you only see the lake once and... watch out for cyclists coming in the opposite direction.
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Montefollonico, a hamlet of Torrita di Siena, is characterized by a discreet and elegant atmosphere, far from the most crowded tourist circuits. From the Chiesa del Triano, a suggestive view opens up over Montepulciano and the typical Tuscan hilly landscape: a privileged spot for a quiet stop and some photos.
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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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Dominated by the imposing Torre del Cassero, this medieval village offers one of the most spectacular views of the Valdichiana and the Val di Chio below. A stop in the Piazza del Municipio allows you to admire the elegant Vasari Loggias, a true natural terrace that frames the Tuscan landscape in a timeless atmosphere.
2
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A circular route of approximately 60 km. Completely on a dirt track (only 2 km on the road). The route is exclusively for cyclists and pedestrians, immersed in nature, with breathtaking views, and from San Feliciano you can see sunsets that heal the soul, so beautiful they are, absolutely worth doing.
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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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Also ideal for gravel bikers! More tips for gravel bike adventures in the area at https://graveldeluxe.com or in my Komoot profile https://www.komoot.de/user/graveldeluxe
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There are over 45 dedicated no-traffic gravel bike routes around Cortona listed in this guide, offering a wide range of experiences for all skill levels. You'll find everything from easy rides to challenging adventures through the Tuscan landscape.
The best time for gravel biking in Cortona is typically during the spring (April to June) and autumn (September to October). During these seasons, the weather is pleasantly mild, and the landscapes are particularly beautiful with blooming flowers or vibrant fall colors. Summers can be hot, especially in July and August, while winters can be cooler and wetter.
Yes, Cortona offers several easy, no-traffic gravel routes perfect for beginners or families. For instance, the Olive Tree at Lake Trasimeno loop from Castiglion del Lago is an excellent choice, offering a gentle ride with minimal elevation gain around the picturesque Lake Trasimeno.
Many no-traffic gravel trails around Cortona offer breathtaking panoramic views of the Valdichiana plain, Lake Trasimeno, and the surrounding rolling hills covered in vineyards and olive groves. You might encounter highlights such as the Monte Acuto Summit Cross or the tranquil Lago di Montepulciano Nature Reserve. The region is also rich in Etruscan heritage and ancient walls.
Absolutely. For experienced riders seeking a challenge, Cortona provides numerous difficult no-traffic gravel routes. A great example is the Panorama over Lake Trasimeno – Lake Trasimeno Cycle Path loop from Torrita di Siena, which features significant elevation changes and covers a substantial distance, testing your endurance amidst stunning scenery.
Yes, many of the no-traffic gravel bike routes around Cortona are designed as circular loops, allowing you to start and end at the same point without retracing your steps. The Bonifica Trail – Lake Trasimeno Cycle Path loop from Cortona is a popular circular option that takes you through diverse landscapes.
The komoot community highly rates the no-traffic gravel trails around Cortona, with an average score of 4.7 stars. Reviewers often praise the serene beauty of the Tuscan countryside, the quiet roads free from vehicle traffic, and the rewarding panoramic views. The blend of natural landscapes, historic towns, and well-maintained gravel paths makes for an unforgettable experience.
While specific parking information varies by trailhead, Cortona and its surrounding towns generally offer public parking areas. It's advisable to check local parking options in towns like Cortona, Castiglion del Lago, or Torrita di Siena, which often serve as starting points for these routes.
Yes, the Cortona region is dotted with charming villages and towns where you can find cafes, restaurants, and accommodation. Many routes pass through or near these spots, allowing for convenient breaks. You might even find unique facilities like the Camping Punta Navaccia - DINAclub e-Bike Charging Station near Lake Trasimeno, which caters to cyclists.
Many routes in the Cortona area naturally blend gravel biking with opportunities for historical and cultural exploration. The region is rich in Etruscan heritage, ancient walls, and picturesque hilltop towns. While specific routes aren't solely dedicated to history, you'll often find yourself cycling past archaeological sites or through historic villages, offering a chance to immerse yourself in Tuscany's past.
Accessing trailheads directly by public transport can be challenging in rural Tuscany. While Cortona itself has train and bus connections, reaching specific, more remote no-traffic gravel trail starting points might require a combination of public transport and a short ride or taxi. Planning your route in advance and checking local transport schedules is recommended.
Yes, the region boasts beautiful natural features. Lake Trasimeno, Italy's fourth-largest lake, is a prominent natural attraction easily accessible from Cortona, and several routes, like the Castiglione del Lago – Lake Montepulciano loop from Castiglion del Lago, incorporate it. You can also visit the Lake Montepulciano, a tranquil nature reserve.


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