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Routes

Bike touring routes & trails

Italy

Tuscany

Arezzo

Castiglion Fiorentino

View of Castiglion Fiorentino – View of Cortona loop from Castiglion Fiorentino

Routes

Bike touring routes & trails

Italy

Tuscany

Arezzo

Castiglion Fiorentino

View of Castiglion Fiorentino – View of Cortona loop from Castiglion Fiorentino

Moderate

5.0

(2)

riders

View of Castiglion Fiorentino – View of Cortona loop from Castiglion Fiorentino

02:49

45.2km

440m

Cycling

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

Last updated: April 15, 2026

Waypoints

Start point

Train Station

Get Directions

498 m

View of Castiglion Fiorentino

Highlight • Viewpoint

A delightful square and a beautiful view of the surrounding plain

Translated by Google •

Tip by

12.6 km

View of Cortona

Highlight • Viewpoint

Beautifully situated town in the south of Tuscany.

Translated by Google •

Tip by

14.7 km

Saint Mary of the Graces at the Calcinaio

Highlight • Religious Site

Legend has it that on Easter Sunday 1484, an image of the Madonna and Child painted on the wall of a vat for tanning leather - and called "calcinaio" because …

Translated by Google •

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15.8 km

Ancient olive groves just before Cortana

Highlight • Natural

During the ascent to Cortana you will pass wonderful, ancient olive groves.

Translated by Google •

Tip by

18.5 km

View of the Valdichiana from Cortona

Highlight • Viewpoint

You will be rewarded with such views when you go to Cortona.

Translated by Google •

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19.9 km

Piazza della Repubblica and Clock Tower, Cortona

Highlight • Historical Site

Here you have to go up - lots of romance and originality make the climb worthwhile.

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19.9 km

View from Piazza Garibaldi

Highlight • Viewpoint

Country of origin of many historical figures but also of the cyclist and singer-songwriter Jovanotti, Cortona stands on a hill and with its Piazza Garibaldi (a small roundabout) allows you …

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45.2 km

End point

Train Station

Way Types & Surfaces

Way Types

28.6 km

9.75 km

6.65 km

185 m

Surfaces

41.4 km

3.48 km

268 m

Elevation

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

Highest point (490 m)

Lowest point (240 m)

Weather

Saturday 23 May

27°C

12°C

0 %

Additional weather tips

Max wind speed: 18.0 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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View of Castiglion Fiorentino – View of Cortona loop from Castiglion Fiorentino

View of Castiglion Fiorentino

View of Cortona

Saint Mary of the Graces at the Calcinaio

Ancient olive groves just before Cortana

View of the Valdichiana from Cortona

Piazza della Repubblica and Clock Tower, Cortona

View from Piazza Garibaldi

Nearby routes

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