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Italy
Tuscany
Siena

From Siena to Castellina in Chianti – loop tour

Routes
Bike touring routes & trails
Italy
Tuscany
Siena

From Siena to Castellina in Chianti – loop tour

Expert

4.8

(8)

201

riders

From Siena to Castellina in Chianti – loop tour

04:41

68.3km

1,140m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: August 13, 2024

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Includes a segment with temporary access restrictions

Check ahead to confirm restricted segments are open to the public.

276 m in total

Waypoints

A

Start point

Parking

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1

14.6 km

Fonterutoli

Highlight • Settlement

Fonterutoli, during the wars between Siena and Florence, was the site of the agreements that put an end to the dispute over the Chianti territories. It is said that the …

Translated by Google •

Tip by

2

16.9 km

Panoramic View from the Chiantigiana

Highlight • Viewpoint

Panoramic view of Siena and Montemaggio

Translated by Google •

Tip by

3

19.4 km

San Salvatore Church, Castellina in Chianti

Highlight • Religious Site

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 •

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4

31.3 km

Radda in Chianti

Highlight • Settlement

Radda is one of the many jewels of Chianti, you can taste locally produced wines and walk around the town to see the ducal palace and the city walls.

Translated by Google •

Tip by

5

46.8 km

Climb up to Castello di Brolio

Highlight (Segment) • Climb

Crossing the entrance gate to Brolio Castle, you enter a dirt road that proceeds steeply uphill surrounded by trees.
You can pedal while enjoying the refreshment of the branches that guide you to the 12th century castle.

Translated by Google •

Tip by

6

47.8 km

Brolio Castle

Highlight • Castle

Brolio Castle, located in Gaiole in Chianti, bears the signs of the most diverse eras of which it is a witness: from the medieval bastions, to the Romanesque, neo-Gothic theme, up to the Tuscan nineteenth century.

Translated by Google •

Tip by

7

52.7 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 •

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B

68.3 km

End point

Parking

Way Types & Surfaces

Way Types

44.6 km

19.5 km

3.53 km

399 m

273 m

Surfaces

64.4 km

3.13 km

595 m

184 m

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Elevation

Elevation

Highest point (620 m)

Lowest point (220 m)

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Weather

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Today

Thursday 30 October

18°C

16°C

100 %

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How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.8

201

From Siena to Castellina in Chianti – loop tour

04:41h

68.3km

1,140m

How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

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From Siena to Asciano – loop tour

04:45h

71.6km

940m

How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.7

163

Strade Bianche Bagnaia e Vidritta da Siena – loop tour

03:58h

58.2km

770m

How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.3

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From Colle Val d’Elsa to San Gimignano

02:48h

37.5km

730m

How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
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03:11h

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How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.2

100

The colors of Chianti — Ring tour

02:14h

27.2km

490m

How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.4

140

From Siena to Monteriggioni and Gracciano d'Elsa

03:42h

53.1km

670m

How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.8

143

From Siena to Passo dell'Incrocati – loop tour

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59.1km

1,010m

How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

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How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
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How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.3

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02:09h

30.1km

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How to understand each route’s difficulty level

Hiking

Bike

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.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

4.4

77

Asciano and Mount Sante Marie - Ring tour

04:37h

61.9km

940m

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