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Monteriggioni Historic Centre – Monteriggioni Castle loop from Poggibonsi-San Gimignano

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Monteriggioni Historic Centre – Monteriggioni Castle loop from Poggibonsi-San Gimignano

Hard

5.0

(5)

riders

Monteriggioni Historic Centre – Monteriggioni Castle loop from Poggibonsi-San Gimignano

04:17

63.5km

900m

Cycling

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: June 13, 2026

Tips

Includes a segment in which cycling is not permitted

After 9.33 km for 78 m

Waypoints

Start point

Train Station

Get Directions

2.22 km

Castello della Magione

Castle

9.36 km

Rocca di Staggia

Castle

14.1 km

Castellina Scalo–Monteriggioni Cycle Path

Highlight • Cycleway

Nice stretch of cycle path that connects the Castellina Scalo station to Monteriggioni; but then be careful because to go up to the town there is a dirt road with some very steep sections!

Translated by Google •

Tip by

15.1 km

Monteriggioni

Highlight • Castle

Monteriggioni is a beautifully preserved medieval fortified town in Tuscany. Built between 1214 and 1219 by the Sienese, the town is situated on a natural hill and is surrounded by impressive walls that form an almost perfect circle. The walls, which are approximately 570 meters long, feature fourteen towers and two gates: the Porta Fiorentina and the Porta Romana. Within the walls, you will find charming streets, a central piazza with a simple Romanesque church, and several historic buildings. Monteriggioni offers a unique glimpse into medieval life and is a popular destination for tourists who want to explore the rich history and architecture of Tuscany.

Translated by Google •

Tip by

15.2 km

Monteriggioni Historic Centre

Highlight • Historical Site

The Castle of Monteriggioni was built by the Sienese, by order of the podestà Guelfo da Porcari, in a period between 1213 and 1219. The land, purchased by the noble Da Staggia family, was the site of an ancient Lombard farm (the name of Montis Regis probably indicated a land owned royally or which enjoyed tax exemptions from the crown).

The construction of the castle by the Republic of Siena had mainly defensive purposes, as the village was built on Mount Ala in a position of dominion and surveillance of the Francigena, to control the Elsa and Staggia valleys in the direction of Florence, historical rival of Siena.
(Wikipedia)

Translated by Google •

Tip by

16.3 km

Monteriggioni Castle

Highlight • Castle

Sections of via francigena between Siena and Monteriggioni. Climb and descend sweet and challenging in one of the most beautiful contexts in Tuscany

Translated by Google •

Tip by

39.1 km

Fonterutoli

Highlight • Settlement

Fonterutoli, during the wars between Siena and Florence, was the site of the agreements that put an end to the dispute over the Chianti territories. It is said that the border should have been established at the meeting point between a Florentine knight and a Sienese knight who should have left their respective cities at the first cockcrow: the meeting between the two knights would have taken place right near Fonterutoli.

Translated by Google •

Tip by

39.8 km

View of Fonterutoli

Highlight • Viewpoint

The panoramic viewpoint looking back on Fonterutoli is breathtaking, especially at sunset. It's also good to know stopping on the roadside cafe in Fonterutoli is worthwhile along your journey. Take a ride behind the cafe to the church and explore the small village of 80 inhabitants.

Tip by

41.3 km

Panoramic View from the Chiantigiana

Highlight • Viewpoint

Panoramic view of Siena and Montemaggio

Translated by Google •

Tip by

44.1 km

Castellina in Chianti

Highlight • Settlement

Castellina in Chianti is located in the province of Siena, in the Chianti Classico area. Accessible from several valleys, it offers breathtaking views. It is a crucial point for cyclists traveling around Chianti. From Elsatal there are four roads that lead up there. At the main intersection there is a fountain and bars nearby.

Translated by Google •

Tip by

63.5 km

End point

Train Station

Way Types & Surfaces

Way Types

45.3 km

7.23 km

5.49 km

2.89 km

1.90 km

533 m

182 m

Surfaces

60.1 km

2.22 km

513 m

481 m

192 m

Elevation

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

Weather

Friday 26 June

38°C

21°C

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Monteriggioni Historic Centre – Monteriggioni Castle loop from Poggibonsi-San Gimignano

Castellina Scalo–Monteriggioni Cycle Path

Monteriggioni

Monteriggioni Historic Centre

Monteriggioni Castle

Fonterutoli

View of Fonterutoli

Panoramic View from the Chiantigiana

Castellina in Chianti

Nearby routes

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