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Castiglion Fiorentino

Castiglion Fiorentino – Cortona loop from Castiglion Fiorentino

Castiglion Fiorentino

Castiglion Fiorentino – Cortona loop from Castiglion Fiorentino

Moderate

4.5

(4)

riders

Castiglion Fiorentino – Cortona loop from Castiglion Fiorentino

02:27

49.3km

630m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: August 17, 2026

Tips

The surface for a segment of your route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 15.3 km for 999 m

Waypoints

Start point

Train Station

Get Directions

1.26 km

Castiglion Fiorentino

Highlight • Settlement

Dominated by the imposing Torre del Cassero, this medieval village offers one of the most spectacular views of the Valdichiana and the Val di Chio below. A stop in the Piazza del Municipio allows you to admire the elegant Vasari Loggias, a true natural terrace that frames the Tuscan landscape in a timeless atmosphere.

Translated by Google •

Tip by

4.58 km

Montecchio Castle

Highlight • Castle

photo of the castle from the state road

Translated by Google •

Tip by

12.7 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 of the lime used in this work - began to perform miracles.
The work on the church lasted from 1485 to 1525.

Translated by Google •

Tip by

14.6 km

Cortona

Highlight • Settlement

Bar La Posta, coffee break and off you go!

Translated by Google •

Tip by

15.5 km

view point

Viewpoint

15.9 km

Down into the historic center of Cortona

Highlight • Viewpoint

Very nice views while riding down into Val di Chiana and entering the historic center of Cortona rather abruptly. It is a steep one way track down, so be sure the brakes are in good condition.

Tip by

25.7 km

Camucia - Corona

Highlight • Cycleway

At the foot of Cortona, which dominates and watches from above, the village of Camucia awaits you after a nice ride on the plain interrupted by the ups and downs of the Umbrian-Tuscan countryside. You can admire the landscapes, refresh yourself, go to the top of Cortona and resume the plain. Suggestive, in winter, the landscape caressed by the fog

Translated by Google •

Tip by

27.4 km

Santa Maria delle Grazie al Calcinaio

Highlight • Religious Site

Ascent to Cortona.

Translated by Google •

Tip by

49.3 km

End point

Train Station

Way Types & Surfaces

Way Types

35.5 km

9.78 km

3.83 km

146 m

119 m

Surfaces

46.9 km

1.12 km

1.06 km

242 m

Elevation

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

Highest point (590 m)

Lowest point (240 m)

Weather

Monday 31 August

33°C

16°C

0 %

Additional weather tips

Max wind speed: 15.0 km/h

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Castiglion Fiorentino – Cortona loop from Castiglion Fiorentino

Castiglion Fiorentino

Montecchio Castle

Saint Mary of the Graces at the Calcinaio

Cortona

Down into the historic center of Cortona

Camucia - Corona

Santa Maria delle Grazie al Calcinaio

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