5.0
(8)
191
riders
02:31
50.1km
830m
Road cycling
This moderate 31.1-mile road cycling loop from Vaggio explores the scenic Chianti region to Figline Valdarno, with 2714 feet of gain.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
24.4 km
Highlight (Segment) • Cycleway
Translated by Google •
Tip by
35.4 km
Highlight • Settlement
Translated by Google •
Tip by
46.8 km
Highlight • Historical Site
Translated by Google •
Tip by
50.1 km
End point
Parking
Way Types & Surfaces
Way Types
46.1 km
2.38 km
873 m
784 m
Surfaces
50.0 km
124 m
Sign up to see more specific route details
Sign up for free
Elevation
Highest point (490 m)
Lowest point (120 m)
Sign up to see more specific route details
Sign up for free
Weather
Powered by Foreca
Monday 25 May
32°C
16°C
0 %
Additional weather tips
Max wind speed: 4.0 km/h
to get more detailed weather forecasts along your route
This route was planned by komoot.
This racebike tour is rated as moderate. It covers a distance of approximately 50 km with a significant elevation gain of around 827 meters, requiring a good level of physical fitness due to the hilly terrain characteristic of the Chianti region.
The terrain is predominantly hilly and winding, traversing the undulating landscape of the Chianti region. While many sections are paved, cyclists should be prepared for potential 'strade bianche' (unpaved dirt roads) which are common in Tuscany. These sections can add to the challenge and require careful handling, even on a racebike.
Along the route, you'll pass through picturesque Tuscan landscapes. Notable highlights include the scenic Provincial Road della Panca, the charming Dudda Village, and in Figline Valdarno, the historic Palazzo Pretorio and Clock Tower. The route offers numerous opportunities for scenic stops amidst vineyards, olive groves, and medieval villages.
The tour starts and ends in Vaggio. While specific designated parking for cyclists in Vaggio is not detailed, it is a small village. You may find street parking available. For more extensive parking options, consider looking in the nearby town of Figline Valdarno.
Cycling with a dog on this racebike route, especially given its moderate difficulty, significant climbs, and potential unpaved sections, can be challenging. While there are no explicit prohibitions against dogs on Tuscan roads, it's important to consider your dog's endurance and safety, as well as local leash laws and the suitability of the terrain for their paws.
The best time to cycle in the Chianti region, including this loop, is typically during the spring (April-June) and autumn (September-October). During these seasons, the weather is generally milder and more pleasant for cycling, avoiding the intense heat of summer and the colder, potentially wetter conditions of winter. This allows for better enjoyment of the stunning Tuscan scenery.
No, you do not need any special permits or to pay entrance fees to cycle on public roads and paths in the Chianti and Figline Valdarno area. The route primarily uses public infrastructure.
Yes, this route briefly intersects with several other paths. You'll find sections that overlap with the
Ciclovia dell'Arno
,Sentiero di crinale del Chianti
, and parts of theEuroVelo 7 - Sun Route - part Italy 2
. It also touches upon local trails likeAnello di Cintoia
andSM1 Sentiero della Memoria Monti Scalari e Pian d'Albero
.The route passes through several villages, including Dudda Village and Figline Valdarno. These towns, especially Figline Valdarno, offer opportunities to find cafes, restaurants, and shops where you can refuel and take a break. Vaggio, the starting point, may also have limited options.
Given its 'moderate' difficulty rating, significant elevation gain of 827 meters, and a distance of 50 km, this route is generally not recommended for absolute beginners. It requires a good level of physical fitness and some experience with road cycling, especially on hilly and potentially mixed-surface terrain.
Cyclists are treated to breathtaking panoramic views of classic Tuscan landscapes. The route winds through picturesque vineyards, olive groves, and dense forests. You'll pass charming medieval villages, ancient castles, and historic abbeys, offering numerous opportunities for scenic stops and cultural exploration.