The Borro Osteria – Good Rest loop from Bucine

The Borro Osteria – Good Rest loop from Bucine

Hard

riders

The Borro Osteria – Good Rest loop from Bucine

04:35

62.1km

830m

Gravel riding

Hard gravel ride. Very good fitness required. Mostly paved surfaces. The starting point of the route is accessible with public transport.

Last updated: October 7, 2026

Waypoints

Start point

Train Station

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18.2 km

The Borro Osteria

Highlight • Restaurant

Thirty kilometers towards this ancient village, on the SETTEPONTI in the municipality of Loro Ciuffenna. Known, as well as for its indisputable beauty (... which these photos do not pay homage!) Because over the years it has often appeared in newspapers and magazines all over the world.
First his villa at the entrance to the town was the residence of Duke Amedeo d'Aosta, then both the residence, which also contained a small zoo, and the whole town of Borro in 1993 were sold by Amedeo d'Aosta, to a great fashion brand, the Ferragamo family.
Now it is Relais & Châteaux, Restaurant and Spa ... but let's go back to the animated nativity scene. All the characters are in motion, it is certainly one of the most beautiful cribs in Tuscany. In a small chapel, located near the church, there is a perfect copy of the Holy Shroud, donated by Duke Amedeo d’Aosta when the Savoy royal family was the owner of the Shroud.

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21.4 km

Entry to Chianti Wine Country

Highlight • Viewpoint

great entry to multiple pathways and quiet riding in beautiful wine country

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23.4 km

Porta San Lorentino, Castiglion Fibocchi

Highlight • Historical Site

It is located on the extreme slopes of the Pratomagno massif, at the point where it moves towards the plain of Arezzo, along the ancient Via Clodia (or Cassia Vetus), the main road that connects Arezzo to Loro Ciuffenna.
The small fraction of Gello Biscardo with its splendidly preserved ancient village also belongs to the municipal territory of Castiglion Fibocchi.
The first settlements were probably in the imperial era; in the early Middle Ages a parish church “Plebs S. Quirini supra Aurum” and six suffragan churches were established.
Its name was "Castrum Leonis de Filiis Bocchi", later reduced to "Castrum de Filiis Bocchi".
Around the year one thousand the area became the property of the Guidi Counts who provided it with a castle to control the road that connected the Valdarno to the Casentino. Later it was given to Ottaviano dei Pazzi del Valdarno.
In 1384 Arezzo and its countryside passed to the Florentine Republic, being enfeoffed in the grand-ducal era as a marquisate to Alessandro del Borro. It was then inserted in the Laterina podesteria.
At the beginning of the 18th century the property of Castiglion Fibocchi was inherited by the Dukes of Lorraine, who abolished feudalism and elevated the village to the rank of an independent municipality, detaching it from the community of the "Two District Municipalities of Laterina".
In 1835, with the victory of the city of Florence over Arezzo, Castiglion Fibocchi was also incorporated into the territory of the Republic of Florence.
In 1860, at the plebiscite organized for the annexation of Tuscany to Sardinia, Castiglion Fibocchi expressed himself with an overwhelming majority in favor of maintaining the separate kingdom (out of 293 having rights, 169 voters, the separate kingdom had 106 votes against 46 which went to the annexation and 17 void). Hence the title of "King of Castiglion Fibocchi" given to Ferdinand IV of Tuscany, who succeeded the last reigning sovereign of Tuscany, Leopold II of Tuscany.

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23.7 km

Cypress Trees View

Highlight • Viewpoint

To visit

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24.1 km

Castiglion Fibocchi Historic Center

Highlight • Historical Site

Municipality of the Province of Arezzo. The historic center is interesting. The street furniture and murals are beautiful, inspired by the Carnival which is celebrated here in a particular way.

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25.6 km

Cypress-Lined Road Through Tuscan Vineyards

Highlight • Viewpoint

Great views indeed. If it is (like for us coming from North) your first view of the Tuscany, it feels like the 'classic landscape' but it will get better continuously ;)

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