4.9
(32)
833
riders
03:07
64.4km
960m
Road cycling
Embark on the Chianti Classico Loop from Siena, a challenging racebike route that takes you through the heart of Tuscany. This difficult 40.0-mile (64.4 km) journey involves a significant climb of 3144 feet (958 metres), typically completed in about 3 hours and 7 minutes. As you pedal, you'll pass through…
Last updated: April 23, 2026
Waypoints
Start point
Parking
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15.4 km
Highlight • Viewpoint
Tip by
19.8 km
Highlight • Monument
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Tip by
22.4 km
Highlight (Segment) • Cycleway
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Tip by
31.1 km
Highlight • Settlement
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Tip by
64.4 km
End point
Parking
Way Types & Surfaces
Way Types
55.4 km
8.52 km
366 m
120 m
< 100 m
Surfaces
64.4 km
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Elevation
Highest point (620 m)
Lowest point (220 m)
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Weather
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Thursday 14 May
17°C
9°C
91 %
Additional weather tips
Max wind speed: 14.0 km/h
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This route was planned by komoot.
This is a challenging racebike route, generally considered difficult. While the exact duration depends on your fitness level and stops, expect it to take over 5 hours to complete due to its significant elevation gains and distance.
The route primarily follows well-maintained asphalt roads, ideal for race biking. However, be prepared for a constantly rolling and sometimes steep profile with significant elevation changes. You might encounter short unpaved sections or cobblestones within historic villages, where you may need to dismount and push your bike.
No, this loop tour is generally classified as difficult and demands a very good level of fitness. It is not recommended for beginners due to its length, significant elevation gain, and challenging terrain.
The best times to cycle this route are typically spring (April-May) and autumn (September-October). During these seasons, the weather is usually pleasant, and the Tuscan landscape is particularly beautiful. Summer can be very hot, and winter may bring colder temperatures and less predictable weather.
The route offers stunning Tuscan vistas, winding through vineyards and olive groves. You'll pass through charming medieval villages like Castellina in Chianti and Radda in Chianti. Notable highlights include the View of Fonterutoli and the Black Rooster Statue in Castellina in Chianti. The town of Radda in Chianti is also a significant stop.
While the tour starts from Siena, specific parking information for cyclists isn't detailed. Siena has various public parking options, particularly outside the historic center, which would be suitable for starting your ride. Consider parking facilities near the city's outskirts for easier access with bikes.
Yes, sections of this route overlap with other established paths. You will find yourself on parts of L'Eroica, Via Romea Sanese - Tappa 4, and Strade Bianche, among others, for portions of the tour.
This route is designed for race biking on public roads. While there are no specific restrictions against dogs, it's generally not considered suitable for bringing dogs along, especially given the distance, difficulty, and traffic conditions. If you plan to stop in villages, local regulations for pets would apply.
No, there are no specific permits or entrance fees required to cycle this public road cycling route through the Chianti Classico region. However, if you plan to visit specific attractions or wineries along the way, they may have their own entry fees.
Yes, the route passes through several charming medieval villages like Castellina in Chianti and Radda in Chianti. These towns offer excellent opportunities to stop for food, water, and local gastronomic delights, including cafes, restaurants, and shops.
Given the route's difficulty and duration, pack essential cycling gear, including a helmet, appropriate cycling apparel, repair kit, and plenty of water. Sun protection is crucial, and consider bringing layers as temperatures can vary. Don't forget your camera for the stunning Tuscan scenery!