4.8
(8)
218
riders
04:41
68.3km
1,140m
Cycling
Cycle the difficult 42.5-mile L'Eroica Chianti Loop from Siena, featuring white gravel roads, vineyards, and Tuscan scenery.
Last updated: February 26, 2026
Tips
Temporary access restrictions
Includes segments with temporary access restrictions. Check ahead to confirm restricted segments are open to the public.
After 19.4 km for 276 m
Waypoints
Start point
Parking
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14.6 km
Highlight • Settlement
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16.9 km
Highlight • Viewpoint
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19.4 km
Highlight • Settlement
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31.3 km
Highlight • Settlement
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46.8 km
Highlight (Segment) • Climb
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47.8 km
Highlight • Castle
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52.7 km
Highlight • Natural Monument
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68.3 km
End point
Parking
Way Types & Surfaces
Way Types
44.7 km
19.5 km
3.59 km
366 m
226 m
Surfaces
64.4 km
3.11 km
625 m
215 m
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Elevation
Highest point (620 m)
Lowest point (220 m)
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Weather
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Tuesday 12 May
22°C
10°C
67 %
Additional weather tips
Max wind speed: 16.0 km/h
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This route was planned by komoot.
This specific Komoot route, a challenging loop from Siena, is approximately 68.3 kilometers (42.4 miles) long with about 1140 meters (3740 feet) of elevation gain. For a touring cyclist, it typically takes around 4 to 5 hours to complete, depending on your pace and stops.
The route offers a classic Tuscan cycling experience, featuring a mix of paved roads and significant stretches of unpaved gravel roads, known as 'strade bianche'. You can expect continuous ups and downs with challenging climbs and descents, winding through vineyards, olive groves, and rolling hills. The gravel sections are a defining feature, requiring good bike handling skills.
This loop takes you through some beautiful Chianti scenery and charming villages. Highlights include the picturesque settlement of Fonterutoli, a Panoramic View from the Chiantigiana, and the historic towns of Castellina in Chianti and Radda in Chianti. You'll also encounter the Climb up to Castello di Brolio, the impressive Brolio Castle, and the ancient Il leccione - secular oak.
No, this route is classified as difficult. While it's shorter than the full L'Eroica permanent route, its significant elevation gain over 68 kilometers and the challenging 'strade bianche' sections require good physical fitness and advanced riding skills. Beginners might find the continuous climbs and gravel surfaces very demanding.
The best times to cycle this route are spring (April to June) and autumn (September to October). During these seasons, the weather is generally mild and pleasant, and the Tuscan landscape is particularly beautiful. Summer can be very hot, making the climbs more challenging, while winter can bring colder temperatures and potentially wet, muddy gravel roads.
Siena has several parking options, particularly outside the historic center. Look for public parking lots such as Parcheggio Fortezza-Stadio or Parcheggio Santa Caterina, which are typically well-located for accessing routes leading out of the city. From these, you can easily start your cycling adventure.
No, there are no specific permits or entrance fees required to cycle this public route. The 'strade bianche' and roads are freely accessible. However, if you plan to visit specific attractions like Brolio Castle, there might be separate entrance fees for those sites.
While the route itself is on public roads and trails where dogs are generally allowed, it's important to consider the nature of the ride. This is a challenging touring bicycle route with significant distance and elevation. Carrying a dog on a bike for this duration and difficulty might not be feasible or comfortable for the animal. If you plan to bring a dog, ensure it's well-trained, accustomed to cycling, and that you have appropriate gear for its safety and comfort.
Yes, this route shares sections with several other paths. Notably, about 36% of the route overlaps with the official 'L'Eroica' permanent route. Smaller portions also intersect with 'Via Romea Sanese - Tappa 4' (11%) and 'Strade Bianche' (6%), among others.
Given the mix of paved and unpaved 'strade bianche' sections, a touring bicycle with robust tires (at least 32mm wide) and good suspension is highly recommended. A gravel bike or a sturdy road bike with wider tires would also be suitable. Standard road bikes with narrow tires might struggle on the gravel sections.
Yes, the route passes through several charming towns and villages like Castellina in Chianti and Radda in Chianti. These settlements offer opportunities to find cafes, restaurants, and shops where you can purchase food and refill your water bottles. It's always wise to carry enough water and snacks, especially between towns.