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Gargonza Castle – Montecchio Vesponi Castle loop from Montagnano

Gargonza Castle – Montecchio Vesponi Castle loop from Montagnano

Hard

4.0

(2)

riders

Gargonza Castle – Montecchio Vesponi Castle loop from Montagnano

05:28

81.2km

1,000m

Gravel riding

Hard gravel 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: June 26, 2026

Waypoints

Start point

Parking

Get Directions

11.1 km

Historic Village of Oliveto

Highlight • Historical Site

beautiful village just above Albergo in the Valdichiana between Arezzo and Monte San Savino, absolutely not to be missed

Translated by Google •

Tip by

20.2 km

Gargonza Water Fountain

Highlight • Rest Area

Fresh water and meeting place.

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20.5 km

Gargonza Climb (La Chianina Ciclostorica)

Highlight (Segment) • Climb

From the crossroads of the state road, go up for about 5 km of dirt road to the castle of Gargonza. Not impossible woods and slopes, dirt road in good condition

Translated by Google •

Tip by

25.5 km

Gargonza Castle

Highlight • Castle

Small and characteristic village with restaurant.

Translated by Google •

Tip by

62.4 km

Montecchio Vesponi Castle dominates the Val di Chio from a hill over 360 meters above sea level. With its crenellated walls, towers, and an imposing 30-meter-high square tower, it is one of the best-preserved medieval castles in Tuscany and can be recognized from afar throughout the valley.

Contested for centuries by Arezzo and Florence for its strategic position on the road to Cortona, it became a Florentine stronghold after the Battle of Campaldino in 1289. In the 14th century, it was also home to the famous mercenary captain John Hawkwood.

Today, the castle comes back to life with guided tours, events, and reenactments that evoke the atmosphere of the Middle Ages.

Translated by Google •

Tip by

64.0 km

View of Montecchio Vespucci Castle and Church

Highlight • Viewpoint

Montecchio Vespucci Castle

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67.1 km

Church of Our Lady of Consolation

Highlight • Religious Site

In Castiglion Fiorentino, just outside the city walls, stands the Church of the Madonna della Consolazione. Its history stems from a sacred image of the Madonna and Child, attributed to Luca Signorelli, once kept in a tabernacle along the road.

Tradition holds that Eleonora di Toledo, wife of Cosimo I de' Medici, regained her sight by praying before that image. In gratitude, she financed the construction of the church, which began in 1565 and was completed only decades later.

Inside, in a side chapel, the original fresco of the Madonna is still preserved.

Translated by Google •

Tip by

67.8 km

View of Castiglion Fiorentino

Highlight • Viewpoint

A delightful square and a beautiful view of the surrounding plain

Translated by Google •

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81.2 km

End point

Parking

Way Types & Surfaces

Way Types

45.5 km

22.3 km

11.7 km

1.65 km

165 m

Surfaces

32.2 km

27.3 km

19.3 km

1.31 km

1.15 km

Elevation

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

Highest point (550 m)

Lowest point (240 m)

Weather

Thursday 9 July

34°C

18°C

28 %

Additional weather tips

Max wind speed: 12.0 km/h

to get more detailed weather forecasts along your route

Comments

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Gargonza Castle – Montecchio Vesponi Castle loop from Montagnano

Historic Village of Oliveto

Gargonza Water Fountain

Gargonza Climb (La Chianina Ciclostorica)

Gargonza Castle

Montecchio Vesponi Castle

View of Montecchio Vespucci Castle and Church

Church of Our Lady of Consolation

View of Castiglion Fiorentino

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