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Bike touring routes & trails
Italy
Tuscany
Siena
Poggibonsi

Beautiful view on San Gimignano – View of San Gimignano loop from Poggibonsi-San Gimignano

Routes
Bike touring routes & trails
Italy
Tuscany
Siena
Poggibonsi

Beautiful view on San Gimignano – View of San Gimignano loop from Poggibonsi-San Gimignano

Moderate

3.7

(3)

79

riders

Beautiful view on San Gimignano – View of San Gimignano loop from Poggibonsi-San Gimignano

02:53

46.6km

380m

Cycling

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

Last updated: May 17, 2026

Tips

Cycling is not permitted along parts of this route

After 14.3 km for 73 m

After 34.3 km for 58 m

Waypoints

A

Start point

Train Station

Get Directions

1

2.33 km

View of San Gimignano

Highlight • Viewpoint

2

14.0 km

Certaldo (Tuscany)

Highlight • Settlement

Certaldo is a Tuscan town with ancient Etruscan-Roman origins. Not far from Florence, it is located in the center of the Valdelsa and has numerous places or buildings of historical, cultural and artistic interest (such as the Palazzo Pretorio and Via Boccaccio), especially in Certaldo Alto, the medieval part that stands on a hill.
The development of the town was favored by the Via Francigena that passed at the base of the hill in the direction of Siena.
Certaldo is famous for being the birthplace of the famous writer Giovanni Boccaccio and artists such as Benozzo Gozzoli or Giovanni della Robbia. Today it hosts numerous festivals and cultural and folk events The largest and most famous is Mercantia, a week-long party in Certaldo Alto, which involves numerous street performers from all over the world.

Tip by

3

31.6 km

Beautiful view on San Gimignano

Highlight • Viewpoint

With a view of San Michele a Strada you are at the border of the town of San Geminiano, the town in Siena famous for its towers and therefore also on the UNESCO World Heritage List.

Translated by Google •

Tip by

4

33.6 km

Sir…back to the past! Like knights on the horse of steel, carbon or aluminum along the path that leads to the fort (the city of San Gimignano).

Translated by Google •

Tip by

5

34.3 km

San Gimignano Historic Centre

Highlight • Historical Site

One of the most typical and fascinating medieval countries (and Unesco heritage) in Tuscany is San Gimignano; it’s is a village that has remained almost intact since the end of the fourteenth century, when it was called the city of one hundred towers, until today. In fact, its main feature were and are the tower-houses, that is, homes that noble families had built by developing them vertically for both defense and prestige purposes. Of these real little fortresses today only 13 remain.
San Gimignano is one of the most visited places in Tuscany (and not only by foreign tourists or from other regions, but also by the Tuscans themselves), yet unfortunately suffers from a mass hit-and-run tourism, for the busloads of groups who arrive in the town, cross it quickly and then leave again. Therefore it is preferable to visit during the low season and out of the weekends.
As for most villages of Middle Ages (when they were particularly careful to emphasize the light, especially inside religious buildings), the most fascinating moments in which to admire San Gimignano are the sunset, when the stone takes the typical reddish hues, and early morning, when a magical bluish mist envelops the silent town and the surrounding countryside.
You can not leave from San Gimignano without having tasted its Vernaccia wine, pecorino cheese or wild boar meat.

Tip by

6

34.3 km

San Matteo Gate

Highlight • Historical Site

San Gimignano is an Italian municipality of 7,743 inhabitants.

Due to the characteristic medieval architecture of its historic center it has been declared a world heritage site by UNESCO. The site of San Gimignano, despite some nineteenth-twentieth century restorations, is mostly intact in its thirteenth-fourteenth century appearance and is one of the best examples in Europe of urban organization of the municipal age.

Granted by Royal Decree of 29 April 1936, San Gimignano boasts the title of city.
(Source: Wikipedia)

Translated by Google •

Tip by

7

35.2 km

San Gimignano is a hill town in Tuscany located southwest of Florence. Surrounded by 13th-century walls, the hub of its historic center is Piazza della Cisterna, a triangular square lined with medieval houses. In the skyline of medieval towers, the Torre Grossa in stone stands out. The Cathedral of San Gimignano is a 12th century church where it is possible to admire the frescoes by Ghirlandaio in the Chapel of Santa Fina.
Source: it.wikipedia.org/wiki/San_Gimignano

Translated by Google •

Tip by

8

35.7 km

View of San Gimignano

Highlight • Viewpoint

Great view of the Tuscan countryside

Translated by Google •

Tip by

36.1 km

Postcard picture

Viewpoint

B

46.6 km

End point

Train Station

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Way Types & Surfaces

Way Types

38.8 km

5.43 km

1.61 km

355 m

173 m

< 100 m

< 100 m

Surfaces

42.8 km

1.83 km

1.76 km

139 m

< 100 m

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Elevation

Elevation

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

Highest point (320 m)

Lowest point (60 m)

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Weather

Powered by Foreca

Sunday 28 June

36°C

22°C

25 %

Additional weather tips

Max wind speed: 14.0 km/h

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