4.4
(1209)
15,919
riders
23
rides
Touring cycling routes around Radda In Chianti traverse a landscape characterized by rolling hills, extensive vineyards, and historic villages. The region offers a mix of paved and unpaved roads, including gravel sections, providing varied terrain for cyclists. Elevation changes are common, with routes featuring significant climbs and descents through the picturesque Chianti countryside.
Last updated: November 5, 2026
4.4
(7)
120
riders
30.8km
02:33
690m
690m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
3.8
(4)
72
riders
31.2km
02:10
570m
570m
Hard bike ride. Very good fitness required. Mostly paved surfaces.

4.3
(11)
51
riders
27.1km
02:03
460m
460m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
5.0
(3)
52
riders
15.7km
01:17
280m
280m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
1.0
(1)
59
riders
15.8km
01:06
230m
230m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
Get access to more routes and recommendations from other explorers.
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Popular around Radda In Chianti
Villages, iconic roads and vineyards – Grand Tour of Chianti
Running among castles, vineyards and hills - Ultra Trail Chianti Castles
Hiking around Radda In Chianti
MTB Trails around Radda In Chianti
Road Cycling Routes around Radda In Chianti
Running Trails around Radda In Chianti

Gravel biking around Radda In Chianti
In Gaiole in Chianti, in Piazza Bettino Ricasoli, stands the monument dedicated to Luciano Berruti, the legendary icon of L'Eroica, along with the famous statue of the Black Rooster, the historic symbol of Chianti Classico. Both works were created in iron by the artist and blacksmith Fabio Zacchei. The monument to Berruti was inaugurated in 2018 to celebrate the heroic spirit of the mythical cyclist, while the Black Rooster sculpture stands over 3 meters tall at the entrance to the village. Furthermore, also in Gaiole, visitors can admire the Ciclofficina Luciano Berruti, a donation from his family that faithfully reconstructs his historic workshop.
1
0
great bar, very popular with cyclists
0
0
A beautiful village in the Chianti hills
0
0
The village of Vertine is a tiny fortified town in the Chianti Valley. Walking through its narrow streets is like taking a journey into the glorious past of this area: the stone walls, entrance arches, and towers are a living testament to this.
1
0
Gaiole in Chianti is a small medieval village, among the most important in the Chianti Valley, best known as the starting and finishing point of L'Eroica, an internationally renowned cycling event.
0
0
Vertine is one of the most charming fortified villages in Chianti, perfectly preserved and rich in history. The castle, dating back to the early 12th century and linked to the Ricasoli family, constitutes the original nucleus of the village, with stone walls and houses clustered within. The entrance is dominated by an imposing 13th-century square tower, built to strengthen defenses during the conflicts between Florence and Siena. Inside the village is the Romanesque church of San Bartolomeo, also from the 12th century, simple and intimate, with original features clearly visible. Strolling through the narrow cobbled streets, you can still breathe in the atmosphere of the Middle Ages, while the views of the Chianti hills make Vertine an ideal stop for those who love history, architecture, and nature.
0
0
Beautiful Tuscan Castle town with nice restuarants and shops. On a high ridge, with great views of the valley below
1
0
The home of Eroica, a great place for a coffee break or lunch mid-ride
0
0
There are over 30 touring cycling routes available around Radda In Chianti, offering a diverse range of experiences through the region's vineyards and historic villages.
The routes traverse a landscape characterized by rolling hills, extensive vineyards, and historic villages. You'll find a mix of paved and unpaved roads, including significant gravel sections, providing varied terrain. Elevation changes are common, with routes featuring climbs and descents through the picturesque Chianti countryside.
While there are no routes specifically classified as 'easy', Radda In Chianti offers 13 moderate touring cycling routes. These routes provide a good balance of challenge and scenic beauty without the extreme demands of the more difficult trails. For example, the Gelateria Sampoli – Radda in Chianti loop from Radda in Chianti is a moderate option that offers a scenic loop through local villages and vineyards.
For experienced riders seeking a challenge, there are 19 difficult touring cycling routes. These often feature extensive gravel roads and significant elevation changes. A notable option is the Crete Senesi – Monte Sante Marie Gravel Road loop from Radda in Chianti, which covers 87.1 miles (140.1 km) and includes substantial climbs through the iconic Crete Senesi landscape.
The ideal time for touring cycling in Radda In Chianti is typically 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 wildflowers in spring and vibrant colors in autumn. Summer can be very hot, and winter may bring colder temperatures and occasional rain.
Yes, many of the touring cycling routes around Radda In Chianti are designed as loops, allowing you to start and finish in the same location. Examples include the Radda in Chianti – Crete Senesi loop from Radda in Chianti, which takes you through rolling hills, and the Panzano in Chianti Village – Radda in Chianti loop from Radda in Chianti.
The region offers beautiful natural sights. You might encounter the ancient Il leccione - secular oak, or explore the serene Bosco di Sant'Agnese Nature Reserve. There's also the tranquil Laghetto del Borro di San Cipriano, a small lake perfect for a peaceful stop.
Absolutely. The Chianti region is rich in history. You can cycle past impressive structures like Montefioralle Castle or the iconic Brolio Castle. The walled village of Monteriggioni and the charming town of Castellina in Chianti also offer fascinating historical insights.
Many routes provide stunning vistas of the rolling Chianti hills and vineyards. For particularly memorable views, look for routes that pass through elevated areas or specific viewpoints. The View of the Conca d'Oro Vineyards, Panzano in Chianti is a highly recommended spot for panoramic scenery.
Yes, gravel roads are a defining characteristic of touring cycling in Radda In Chianti. Many routes, especially the more challenging ones, incorporate extensive gravel sections, offering an authentic experience of the Tuscan countryside. The Crete Senesi – Monte Sante Marie Gravel Road loop from Radda in Chianti is a prime example, known for its significant gravel stretches.
The touring cycling routes in Radda In Chianti are highly rated by the komoot community, with an average score of 4.4 stars from over 80 reviews. Cyclists often praise the beautiful vineyard landscapes, the charm of the historic villages, and the challenging yet rewarding nature of the climbs and descents. Many appreciate the diverse terrain, including the iconic gravel roads.


Browse the best Cycling routes in other regions.