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Italy
Tuscany
Siena
Radda In Chianti

Radda in Chianti – Porta Romana (Siena) loop from Radda in Chianti

Routes
Road cycling routes
Italy
Tuscany
Siena
Radda In Chianti

Radda in Chianti – Porta Romana (Siena) loop from Radda in Chianti

Hard

5.0

(4)

80

riders

Radda in Chianti – Porta Romana (Siena) loop from Radda in Chianti

04:13

62.0km

1,030m

Road cycling

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: October 16, 2026

Tips

Includes a segment in which cycling is not permitted

After 25.7 km for 152 m

Waypoints

A

Start point

Bus stop

Get Directions
1

17 m

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

2

38 m

Eroica is the annual non-competitive cycling event that takes place in Chianti and starts at this specific highlight spot.

Tip by

3

27.2 km

Porta Romana (Siena)

Highlight • Monument

Porta Romana is one of the ancient gates in the walls of Siena, located on the path of the ancient Via Cassia which looks south towards Rome.
Porta Romana is …

Translated by Google •

Tip by

28.5 km

Palazzo Sansedoni

Castle

5

46.1 km

View of Fonterutoli

Highlight • Viewpoint

The climb from Fonterutoli to Castellina in Chianti is very characteristic, alternating views with wooded areas in which to shelter from the summer sun, does not have prohibitive slopes, the maximum 7/8%, average 5.5%

Translated by Google •

Tip by

6

49.7 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 •

Tip by

7

50.4 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 …

Translated by Google •

Tip by

8

50.7 km

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, …

Translated by Google •

Tip by

9

53.3 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.

Translated by Google •

Tip by

B

62.0 km

End point

Bus stop

Loading

Way Types & Surfaces

Way Types

31.1 km

25.1 km

3.88 km

1.44 km

510 m

< 100 m

Surfaces

51.5 km

5.72 km

3.62 km

1.08 km

< 100 m

< 100 m

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Elevation

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

Highest point (610 m)

Lowest point (250 m)

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Weather

Powered by Foreca

Saturday 24 October

16°C

4°C

28 %

Additional weather tips

Max wind speed: 9.0 km/h

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Comments

March 4, 2024,Siena pasta ride out
Just awesome. Relaxed get out of Siena and eat some pasta. According to Whoop, I was well rested. If you would like to test Whoop, I have a link for you here. The first month is free!

Get a free WHOOP 4.0 and a month free when you sign up using my link: join.whoop.com/8000watt

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