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Bike touring routes & trails

Italy

Tuscany

Siena

Castellina In Chianti

View of Fonterutoli – Radda in Chianti loop from Fonterutoli

Routes

Bike touring routes & trails

Italy

Tuscany

Siena

Castellina In Chianti

View of Fonterutoli – Radda in Chianti loop from Fonterutoli

Hard

4.9

(7)

2,193

riders

View of Fonterutoli – Radda in Chianti loop from Fonterutoli

03:24

50.8km

790m

Cycling

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: March 27, 2026

Waypoints

Start point

Parking

Get Directions

181 m

Fonterutoli

Highlight • Settlement

Fonterutoli, during the wars between Siena and Florence, was the site of the agreements that put an end to the dispute over the Chianti territories. It is said that the border should have been established at the meeting point between a Florentine knight and a Sienese knight who should have left their respective cities at the first cockcrow: the meeting between the two knights would have taken place right near Fonterutoli.

Translated by Google •

Tip by

908 m

View of Fonterutoli

Highlight • Viewpoint

The panoramic viewpoint looking back on Fonterutoli is breathtaking, especially at sunset. It's also good to know stopping on the roadside cafe in Fonterutoli is worthwhile along your journey. Take a ride behind the cafe to the church and explore the small village of 80 inhabitants.

Tip by

9.76 km

Valico Macia Morta

Mountain Pass

15.4 km

Sanctuary of Our Lady of Grace, Pietracupa

Highlight • Religious Site

The Sanctuary of the Madonna delle Grazie is located in Pietracupa in the immediate surroundings of San Donato in Poggio in the municipality of Tavernelle Val di Pesa, in the province of Florence.
It is considered one of the most balanced examples of minor religious architecture located in the Florentine countryside

Translated by Google •

Tip by

18.7 km

Osteria Uscio e Bottega

Highlight • Settlement

Going towards San Donato, the church of San Miniato in Sicelle suddenly appears behind a curve.

Translated by Google •

Tip by

34.8 km

Radda in Chianti

Highlight • Settlement

A walk through the narrow, winding streets and numerous ornate vaulted passages transports you back to bygone medieval times, as if Radda were still the capital of the “Lega del Chianti”.

Translated by Google •

Tip by

45.0 km

View of a Chianti Hillside Village

Highlight • Viewpoint

46.1 km

Black Rooster Statue, Castellina in Chianti

Highlight • Monument

Castellina in Chianti is located in the province of Siena, in the Chianti Classico area. He is easily accessible from the Elsa Valley, Arbiatal and Pesatal. Due to the altitude, the place also offers great views into these valleys.
For us racing cyclists it is an important traffic junction for tours in the Chianti area or for round trips in it.
Four roads lead up from the Elsa Valley alone.
There is a fountain at the main intersection and some bars around it.

Translated by Google •

Tip by

48.9 km

Panoramic View from the Chiantigiana

Highlight • Viewpoint

Panoramic view of Siena and Montemaggio

Translated by Google •

Tip by

50.8 km

End point

Parking

Way Types & Surfaces

Way Types

25.5 km

24.1 km

522 m

405 m

200 m

< 100 m

Surfaces

49.6 km

471 m

427 m

233 m

< 100 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (620 m)

Lowest point (270 m)

Weather

Wednesday 13 May

20°C

8°C

20 %

Additional weather tips

Max wind speed: 28.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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View of Fonterutoli – Radda in Chianti loop from Fonterutoli

Fonterutoli

View of Fonterutoli

Sanctuary of Our Lady of Grace, Pietracupa

Osteria Uscio e Bottega

Radda in Chianti

View of a Chianti Hillside Village

Black Rooster Statue, Castellina in Chianti

Panoramic View from the Chiantigiana

Nearby routes

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