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Rocca of Castellina in Chianti – Castellina in Chianti loop from Mensanello

Rocca of Castellina in Chianti – Castellina in Chianti loop from Mensanello

Hard

riders

Rocca of Castellina in Chianti – Castellina in Chianti loop from Mensanello

05:20

107km

1,710m

Road cycling

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

Last updated: June 27, 2026

Tips

Temporary access restrictions

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

After 21.3 km for 277 m

Waypoints

Start point

Bus stop

Get Directions

20.8 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 …

Translated by Google •

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21.5 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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21.8 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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66.6 km

SR429: Castellina in Chianti to Radda in Chianti

Highlight (Segment) • Cycleway

This pretty road (SR429), between Castellina in Chianti and Radda in Chianti, is always winding and winding at about 600 meters above sea level. It is a delightful ride with always very beautiful views of the surrounding valleys and hills.

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77.3 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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86.9 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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101 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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104 km

Bridge over the Elsa River

Highlight • Bridge

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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107 km

End point

Bus stop

Way Types & Surfaces

Way Types

57.2 km

48.4 km

900 m

723 m

214 m

Surfaces

107 km

373 m

< 100 m

Elevation

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

Highest point (610 m)

Lowest point (100 m)

Weather

Tuesday 14 July

36°C

19°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

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Rocca of Castellina in Chianti – Castellina in Chianti loop from Mensanello

Rocca of Castellina in Chianti

Castellina in Chianti

Black Rooster Statue, Castellina in Chianti

SR429: Castellina in Chianti to Radda in Chianti

Strada del Pestello

Vineyards Between Poggibonsi and Castellina in Chianti

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

Bridge over the Elsa River

Nearby routes

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