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Routes
Bike touring routes & trails
Italy
Tuscany
Siena
Pienza

Monticchiello – Pienza loop from Monticchiello

Routes
Bike touring routes & trails
Italy
Tuscany
Siena
Pienza

Monticchiello – Pienza loop from Monticchiello

Expert

4.8

(113)

509

riders

Monticchiello – Pienza loop from Monticchiello

03:21

40.7km

840m

Expert 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: October 21, 2025

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Includes a segment that goes up or down a series of steps

You may need to carry your bike.

4 m in total

Waypoints

A

Start point

Bus stop

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1

0 m

Monticchiello

Highlight • Settlement

Monticchiello is a fraction of the Italian municipality of Pienza, in the province of Siena, in Tuscany.
It is a typical medieval village immersed in the Sienese countryside. Monticchiello rises …

Translated by Google •

Tip by

2

8.02 km

Strada Bianca to Pienza

Highlight (Segment) • Trail

Definitely worth the trip.. beautiful scenery at every turn!

Tip by

3

21.6 km

Strade Bianche

Highlight • Cycleway

4

32.2 km

I Cipressini Farmhouse

Highlight • Structure

Typical country house on a hilltop. Simply a beautiful motif.

Translated by Google •

Tip by

5

34.0 km

View of the Tuscan Countryside

Highlight • Viewpoint

6

34.7 km

Pienza

Highlight • Settlement

A medieval city, awarded by UNESCO as a World Heritage Site. You can enjoy some old churches and palaces here or simply stroll through the atmospheric streets. Also the view from the city wall is great.

Translated by Google •

Tip by

7

34.7 km

Pienza Cathedral

Highlight • Religious Site

Gravel Pienza San Quirico Vignoni High Bagno Vignoni Pienza

Translated by Google •

Tip by

8

36.9 km

View of Pienza

Highlight • Viewpoint

Beautiful panorama of the city of Pienza

Translated by Google •

Tip by

B

40.7 km

End point

Bus stop

Way Types & Surfaces

Way Types

17.9 km

12.6 km

5.69 km

4.43 km

< 100 m

< 100 m

Surfaces

19.1 km

10.5 km

9.53 km

955 m

579 m

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Elevation

Elevation

Highest point (510 m)

Lowest point (250 m)

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Weather

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Today

Friday 24 October

18°C

12°C

0 %

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Max wind speed: 16.0 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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Expert
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Expert
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Easy
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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.
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Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
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Intermediate
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Corresponds approx. to SAC 2-3.
Expert
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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.
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Expert
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Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
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Mountain Bike

Road Bike

Running

Easy
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Intermediate
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Expert
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Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
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How to understand each route’s difficulty level

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Mountain Bike

Road Bike

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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.
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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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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
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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.
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How to understand each route’s difficulty level

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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.
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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

4.6

78

From Montalcino to Buonconvento

02:13h

30.2km

520m

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