Giocondo Castle – Montalcino Fortress loop from Castelgiocondo

Bike touring routes & trails

Giocondo Castle – Montalcino Fortress loop from Castelgiocondo

Moderate

5.0

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riders

Giocondo Castle – Montalcino Fortress loop from Castelgiocondo

01:42

18.8km

390m

Cycling

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Last updated: August 1, 2026

Waypoints

Start point

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160 m

Giocondo Castle

Highlight • Castle

CastelGiocondo is an ancient fortress built in 1100 to defend the road that led from the sea to Siena.
Today owned by the Frescobaldi agricultural company, it can be visited by reservation. frescobaldi.com/it/tenute/tenuta-castelgiocondo

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4.19 km

Viewpoint toward Montalcino

Highlight • Viewpoint

7.69 km

Montalcino

Highlight • Settlement

wine, gravel riding, eroica.. what could be better?

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9.21 km

View of Montalcino’s historic center

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Land of Tuscany, land of bikes and landscapes that fill the eyes. Montalcino can be the starting or finishing point for a fantastic bike tour on the permanent routes of the Eroica.

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9.73 km

Eroica Montalcino 70 km route

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The starting point is a free parking lot from Saturday to Sunday. On the other days you can park for a maximum of 45 min.

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10.1 km

Montalcino Fortress

Highlight • Castle

The historic center of Montalcino is dominated by the mighty Rocca, a fortress built in 1361 to mark the passage of the city under the dominion of Siena. The panorama …

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