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

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

Hard

3.7

(3)

riders

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

04:13

61.8km

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: April 20, 2026

Tips

Includes a segment in which cycling is not permitted

After 25.7 km for 152 m

Waypoints

Start point

Bus stop

Get Directions

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

38 m

Start of L'Eroica in Gaiole in Chianti

Highlight • Cycleway

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

Tip by

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

46.1 km

View of Fonterutoli

Highlight • Viewpoint

The panoramic viewpoint looking back on Fonterutoli is breathtaking, especially at sunset. It's also good to know stopping on the roadside cafe in Fonterutoli is worthwhile along your journey. Take …

Tip by

49.6 km

Gelateria di Castellina

Highlight • Cafe

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

Tip by

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

50.5 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, …

Translated by Google •

Tip by

53.1 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

61.8 km

End point

Bus stop

Way Types & Surfaces

Way Types

31.6 km

25.1 km

3.70 km

1.16 km

320 m

< 100 m

Surfaces

51.7 km

5.67 km

3.39 km

1.05 km

< 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 (250 m)

Weather

Thursday 21 May

27°C

13°C

0 %

Additional weather tips

Max wind speed: 11.0 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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Radda in Chianti – Porta Romana (Siena) loop from Radda in Chianti

Radda in Chianti

Start of L'Eroica in Gaiole in Chianti

Porta Romana (Siena)

View of Fonterutoli

Gelateria di Castellina

Rocca of Castellina in Chianti

Black Rooster Statue, Castellina in Chianti

SR429: Castellina in Chianti to Radda in Chianti

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