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Routes

Bike touring routes & trails

Italy

Tuscany

Arezzo

Castiglion Fiorentino

View of Castiglion Fiorentino – View of Valdichiana loop from Castiglion Fiorentino

Routes

Bike touring routes & trails

Italy

Tuscany

Arezzo

Castiglion Fiorentino

View of Castiglion Fiorentino – View of Valdichiana loop from Castiglion Fiorentino

Hard

4.0

(4)

riders

View of Castiglion Fiorentino – View of Valdichiana loop from Castiglion Fiorentino

02:18

32.0km

480m

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 26, 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

3.48 km

View of Montecchio Vespucci Castle and Church

Highlight • Viewpoint

Montecchio Vespucci Castle

Translated by Google •

Tip by

11.7 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

12.8 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 •

Tip by

14.4 km

View of the Valdichiana from Cortona

Highlight • Viewpoint

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

Translated by Google •

Tip by

15.8 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.

Translated by Google •

Tip by

15.8 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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Tip by

16.3 km

View of Valdichiana

Highlight • Viewpoint

Going up to Cortona, a beautiful view will open up starting from Lake Trasimeno (left), passing through Monte Cetona, Montepulciano and, in the background, the majestic peak of Monte Amiata.

Translated by Google •

Tip by

32.0 km

End point

Train Station

Way Types & Surfaces

Way Types

17.4 km

8.50 km

5.25 km

562 m

219 m

Surfaces

19.3 km

8.23 km

4.20 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 (250 m)

Weather

Sunday 12 July

34°C

17°C

0 %

Additional weather tips

Max wind speed: 7.0 km/h

to get more detailed weather forecasts along your route

Comments

September 24, 2025,Radtour nach Cortona

We went on a lovely exploratory tour of the picturesque town of Cortona. On the way back, we drove up to the Castello di Montecchio Vesponi, which was unfortunately closed. In the distance, we could see Lake Trasimeno, Italy's fourth-largest lake.

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View of Castiglion Fiorentino – View of Valdichiana loop from Castiglion Fiorentino

View of Castiglion Fiorentino

View of Montecchio Vespucci Castle and Church

Ancient olive groves just before Cortana

Saint Mary of the Graces at the Calcinaio

View of the Valdichiana from Cortona

Piazza della Repubblica and Clock Tower, Cortona

View from Piazza Garibaldi

View of Valdichiana

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