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Castellina in Chianti – Rocca of Castellina in Chianti loop from Gracciano dell'Elsa

Castellina in Chianti – Rocca of Castellina in Chianti loop from Gracciano dell'Elsa

Moderate

5.0

(10)

207

riders

Castellina in Chianti – Rocca of Castellina in Chianti loop from Gracciano dell'Elsa

02:28

50.6km

750m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: May 17, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions. Check ahead to confirm restricted segments are open to the public.

After 29.8 km for 304 m

Waypoints

Start point

Bus stop

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2.35 km

Fountain at Piazza Bartolomeo Scala, Colle di Val d'Elsa

Highlight • Monument

Colle di Val d'Elsa is less known than many of the famous neighboring villages. Nevertheless, it has a lot to offer.
For us racing cyclists, it is above all an …

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17.0 km

Vineyards Between Poggibonsi and Castellina in Chianti

Highlight • Cycleway

The most beautiful descent from Castellana in Chianti, little traffic, great asphalt, pleasant incline, vineyards for wine tasting

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23.0 km

Strada del Pestello

Highlight (Segment) • Cycleway

The road that connects Castellina to Poggibonsi, known as Pestello, made up or down gives great emotions. Smooth and well maintained asphalt, very little traffic

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29.6 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, …

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29.9 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 …

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30.6 km

Rocca of Castellina in Chianti

Highlight • Castle

Castellina in Chianti stands on a chain of hills in the Chianti area. The heart of the town is the ancient fortress, designed in the second half of the fifteenth …

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30.6 km

Gelateria di Castellina

Highlight • Cafe

The best gelato in Chianti. Try it and tell us we are wrong...

Tip by

50.5 km

Beautiful crossing on the Elsa River. If you have time there is a path that leads from the bridge to the river where it is pleasant to dip your feet in the summer! A little further on the Diborrato waterfalls!

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50.6 km

End point

Bus stop

Way Types & Surfaces

Way Types

24.3 km

21.8 km

3.31 km

1.28 km

< 100 m

Surfaces

50.3 km

229 m

163 m

Elevation

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

Highest point (600 m)

Lowest point (100 m)

Weather

Monday 1 June

29°C

16°C

39 %

Additional weather tips

Max wind speed: 18.0 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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Castellina in Chianti – Rocca of Castellina in Chianti loop from Gracciano dell'Elsa

Fountain at Piazza Bartolomeo Scala, Colle di Val d'Elsa

Vineyards Between Poggibonsi and Castellina in Chianti

Strada del Pestello

Black Rooster Statue, Castellina in Chianti

Castellina in Chianti

Rocca of Castellina in Chianti

Gelateria di Castellina

Bridge over the Elsa River

Nearby routes

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