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Certaldo

Monteriggioni Castle – Radda in Chianti loop from Certaldo

Routes
Road cycling routes
Italy
Tuscany
Florence
Certaldo

Monteriggioni Castle – Radda in Chianti loop from Certaldo

Expert

5.0

(1)

96

riders

Monteriggioni Castle – Radda in Chianti loop from Certaldo

05:52

124km

1,550m

Expert 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: November 1, 2025

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466 m in total

Waypoints

A

Start point

Train Station

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1

32.7 km

Monteriggioni Medieval Village

Highlight • Settlement

The approximately 600 m long fortress wall on top of the hill is already visible from afar. In the round of these walls today it is very touristy. Still worth …

Translated by Google •

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2

33.3 km

Monteriggioni Castle

Highlight • Castle

Sections of via francigena between Siena and Monteriggioni. Climb and descend sweet and challenging in one of the most beautiful contexts in Tuscany

Translated by Google •

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3

79.0 km

Radda in Chianti

Highlight • Settlement

Radda in Chianti is a typical Chianti village surrounded by vineyards, where the permanent route of L'Eroica passes. In addition to a walk through the streets of the center, a …

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4

82.7 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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5

91.2 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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6

92.0 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, …

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7

93.5 km

Panoramic road between Castellina in Chianti and San Donato

Highlight (Segment) • Cycleway

From Castellina in Chianti, the SP101 heads north.
Directly behind the town sign comes the road leads beautifully on or right and left of the ridge. Little traffic and fantastic …

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8

113 km

Marcialla Village

Highlight • Settlement

Fantastic Chianti country road

Tip by

B

124 km

End point

Train Station

Way Types & Surfaces

Way Types

66.0 km

54.7 km

2.61 km

610 m

309 m

Surfaces

124 km

489 m

< 100 m

< 100 m

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Elevation

Elevation

Highest point (620 m)

Lowest point (60 m)

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Weather

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Today

Tuesday 4 November

18°C

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

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Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
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Intermediate
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Expert
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Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
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