Castellina in Chianti – San Donato in Poggio loop from Barberino Val d'Elsa

Bike touring routes & trails

Castellina in Chianti – San Donato in Poggio loop from Barberino Val d'Elsa

Hard

5.0

(3)

riders

Castellina in Chianti – San Donato in Poggio loop from Barberino Val d'Elsa

03:47

56.7km

850m

Cycling

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: August 20, 2026

Tips

Includes a segment in which cycling is not permitted

After 48.8 km for 251 m

Waypoints

Start point

Train Station

Get Directions

3.79 km

View of San Gimignano

Highlight • Viewpoint

6.90 km

Scenic Road from Poggibonsi to Castellina in Chianti

Highlight (Segment) • Trail

If you are looking for a scenic, low-traffic and relaxed road up to Castellina in Chianti you will find it here.
On the approximately 18 kilometers with 450 meters of altitude, the slope remains exceptionally even and never rises above 4, a maximum of just 5%.
A pleasure trip ...

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Tip by

25.0 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.

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Tip by

25.2 km

Castellina in Chianti

Highlight • Settlement

Castellina in Chianti is located in the province of Siena, in the Chianti Classico area. Accessible from several valleys, it offers breathtaking views. It is a crucial point for cyclists traveling around Chianti. From Elsatal there are four roads that lead up there. At the main intersection there is a fountain and bars nearby.

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Tip by

26.3 km

View of the Chianti Hills

Highlight • Viewpoint

30.4 km

Valico Macia Morta

Mountain Pass

36.0 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

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Tip by

37.3 km

San Donato in Poggio

Highlight • Historical Site

San Donato is a small medieval village located on top of a hill. We are in the Chianti area and the road you take to first reach San Donato, then Greve and Castellina in Chianti is one of the most beautiful and fascinating in the Tuscan wine region.

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Tip by

38.0 km