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Routes
Bike touring routes & trails
Italy
Tuscany
Siena
Gaiole In Chianti

Brolio Castle – Porta Romana (Siena) loop from Gaiole in Chianti

Routes
Bike touring routes & trails
Italy
Tuscany
Siena
Gaiole In Chianti

Brolio Castle – Porta Romana (Siena) loop from Gaiole in Chianti

Hard

4.9

(15)

558

riders

Brolio Castle – Porta Romana (Siena) loop from Gaiole in Chianti

07:49

106km

1,680m

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: September 9, 2026

Tips

Includes a segment in which cycling is not permitted

After 33.5 km for 256 m

Waypoints

A

Start point

Bus stop

Get Directions
1

11.1 km

Brolio Castle

Highlight • Castle

The castle of Brolio, surrounded by the vines that produce the most famous wines in the world. For bicycle lovers it is located on the permanent route of the Eroica, for wine lovers its cellar cannot miss a visit.

Translated by Google •

Tip by

2

16.0 km

Il leccione - secular oak

Highlight • Natural Monument

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 …

Translated by Google •

Tip by

33.6 km

Palazzo Chigi Zondadari

Castle

4

34.9 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

5

45.1 km

Crete Senesi

Highlight • Natural

One of the most beautiful sections of the Strade Bianche gf

Translated by Google •

Tip by

6

48.3 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

7

51.3 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

8

54.8 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. …

Translated by Google •

Tip by

9

80.6 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

B

106 km

End point

Bus stop

Loading

Way Types & Surfaces

Way Types

65.8 km

20.1 km

12.9 km

6.67 km

219 m

< 100 m

Surfaces

63.4 km

21.7 km

17.5 km

1.79 km

1.23 km

< 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 (510 m)

Lowest point (160 m)

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Weather

Powered by Foreca

Friday 9 October

22°C

11°C

12 %

Additional weather tips

Max wind speed: 9.0 km/h

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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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