Sansepolcro Cathedral – Hermitage of Montecasale loop from Santa Fiora

Sansepolcro Cathedral – Hermitage of Montecasale loop from Santa Fiora

Hard

riders

Sansepolcro Cathedral – Hermitage of Montecasale loop from Santa Fiora

02:32

38.9km

1,080m

Road cycling

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

Last updated: November 4, 2026

Waypoints

Start point

Train Station

Get Directions

3.40 km

Church of Saint Augustine

Highlight • Religious Site

The church has been known as the Church of Santa Maria Assunta since 1203. The church changed its name to Sant'Agostino in 1555, when the Augustinian friars came to Sansepolcro. The church's current appearance is the result of an architectural renovation carried out between 1771 and 1785 based on a design by the architect Vincenzo Righi da Camerino.

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4.02 km

Sansepolcro

Highlight • Settlement

Belonging to the province of Arezzo, Tuscany, Sansepolcro is located in an advantageous position on the borders between four regions: Tuscany, Umbria, Marche and Emilia Romagna. City of art, it is the town of Piero della Francesca and you can visit his birthplace, as well as seeing the various museums, the cathedral and the medieval-Renaissance squares.

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4.20 km

Sansepolcro Cathedral

Highlight • Religious Site

Tradition has it that the city was founded around the 10th century by two pilgrims returning from the Holy Land. To preserve the relics from the Holy Sepulchre, they built an oratory with an adjoining hospital for pilgrims. The town of Borgo San Sepolcro was born around these buildings, later transformed into Sansepolcro. The current appearance of the center is from the Renaissance period, parts of the city walls built by the Medici family are still present.

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11.1 km

Waterfalls of the Afra Stream

Highlight • Waterfall

In this stretch of road there are many waterfalls that both the Afra stream and its tributaries form in the descent to the valley ... beautiful.

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19.8 km

Hermitage of Montecasale

Highlight • Religious Site

The hermitage of Montecasale is one of the most important places linked to the life of Saint Francis. It was the Saint himself who founded the hermitage inside a pre-existing building donated to him by the bishop of Città di Castello. It is also said that the wooden statue of the Madonna with Child was brought by Francis himself, even if there is no certain evidence of this. Its current appearance dates back to the 16th century. Outside the convent are visible: the source of “Grappa l'Orso” where the three thieves drank; the fountain of San Francesco, according to some, created by himself; the Sasso Spicco, where it is said that Francis competed with a nightingale in singing the praises of God, and the little garden where, according to tradition, Francis tested the ability of obedience of two young men eager to become friars.

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30.9 km

Casa di Montevicchi

Ruins

38.9 km

End point

Train Station

Way Types & Surfaces

Way Types

34.5 km

2.73 km