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

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Bike touring routes & trails

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

Hard

4.9

(15)

554

riders

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

08:36

116km

2,020m

Cycling

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: June 11, 2026

Tips

Includes a segment in which cycling is not permitted

After 39.1 km for 256 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

21.5 km

The "Leccione" is a secular tree and represents an iconic icon of Gaiole in Chianti. With the splendid panorama of Siena in the background, these two majestic holm oaks embrace each other, creating a perfect frame for a unique panorama.
The particularity of this centuries-old specimen absolutely deserves a souvenir photo! Don't miss it when you visit this wonderful location.

Translated by Google •

Tip by

39.1 km

Palazzo Chigi Zondadari

Castle

40.4 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 one of the ancient gates in the walls of Siena, located on the route of the ancient Via Cassia that looks south towards Rome.

Translated by Google •

Tip by

50.6 km

Crete Senesi

Highlight • Natural

One of the most beautiful sections of the Strade Bianche gf

Translated by Google •

Tip by

53.8 km

Radi Village

Highlight • Settlement

Uphill on dirt road that reaches Radi... On the road we find a fountain and a bar for refreshments

Translated by Google •

Tip by

56.8 km

Cypress-lined hills and sunflower fields on the Via Francigena, Crete Senesi

Highlight (Segment) • Viewpoint

Little traffic and easy to ride with a gravel bike, but a racing bike with 25mm should work too.

Translated by Google •

Tip by

60.3 km

Strade Bianche – San Martino in Grania to Monteroni d'Arbia

Highlight (Segment) • Cycleway

Sector 7 from the famous Strade Bianche race, officially run from Monteroni d'Arbia in the southwest where the end is especially steep uphill, but great for cycling in both directions. Just a little nicer on the gravel bike than on the racing bike.

Translated by Google •

Tip by

86.1 km

The cypresses of Catignano

Highlight • Viewpoint

View of Siena behind the row of cypresses.
View of Siena behind the line of cypresses.

Translated by Google •

Tip by

116 km

End point

Bus stop

Way Types & Surfaces

Way Types

82.3 km

14.4 km

12.2 km

6.71 km

219 m

< 100 m

Surfaces

74.2 km

21.7 km

17.0 km

1.79 km

1.26 km

Elevation

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

Highest point (520 m)

Lowest point (160 m)

Weather

Saturday 11 July

34°C

19°C

17 %

Additional weather tips

Max wind speed: 8.0 km/h

to get more detailed weather forecasts along your route

Comments

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

Radda in Chianti

Il leccione - secular oak

Porta Romana (Siena)

Crete Senesi

Radi Village

Cypress-lined hills and sunflower fields on the Via Francigena, Crete Senesi

Strade Bianche – San Martino in Grania to Monteroni d'Arbia

The cypresses of Catignano

Nearby routes

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