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Italy
Tuscany
Siena

San Gimignano

The best cycling routes around San Gimignano

4.3

(1238)

12,197

riders

64

rides

Touring cycling around San Gimignano offers routes through the quintessential Tuscan landscape, characterized by rolling hills, expansive vineyards, and ancient olive groves. The terrain includes roads lined with cypress and pine trees, transitioning between open fields and low-lying forests. Elevation changes provide both challenge and panoramic views, including vistas towards Volterra and the Val d'Elsa.

Best touring cycling routes around San Gimignano

  • The most popular touring cycling route is San Gimignano — Ring tour, an 18.2 miles (29.3 km) trail that takes 2 hours 24 minutes to complete. This difficult route offers views of the surrounding Tuscan countryside.
  • Another top favourite among local touring cyclists is View of San Gimignano – Piazza dei Priori, Volterra loop from San Gimignano, a difficult 40.3 miles (64.9 km) path. This route traverses scenic hills and provides views towards the historic town of Volterra.
  • Local touring cyclists also love the View of San Gimignano – Monteriggioni Castle loop from San Gimignano, a 48.3 miles (77.7 km) trail leading through the Tuscan landscape, often completed in about 5 hours 2 minutes. This difficult route passes by medieval villages and fortified castles.
  • Touring cycling around San Gimignano is defined by rolling hills, vineyards, and medieval villages. The network offers options for different ability levels, from easy rides to more challenging routes.
  • The routes in San Gimignano are highly rated by the komoot community with an average score of 4.3 stars from over 300 reviews. More than 2,500 touring cyclists have used komoot to explore San Gimignano's varied terrain.

Last updated: June 30, 2026

4.1

(22)

63

riders

#1.

San Gimignano — Ring tour

29.3km

02:24

570m

570m

Hard bike ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Popular around San Gimignano

A cycling pilgrimage — history and nature on Italy’s Via Francigena

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A cycling pilgrimage — history and nature on Italy’s Via Francigena

Cycling Collection by

Nicola Amadini

Tips from the Community

GIUSEPPE LEONARDI
October 28, 2025, View of Val d'Era

Fun trail but be careful when riding...not for beginners

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I discovered this village thanks to the Tuscany Trail, which at first glance seems like an ordinary village once you reach the main square, but then you discover that there is a higher part with a terrifying climb, but once at the top you will forget all the effort

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A charming, but not very touristy, town on the Via Francigena, about two-thirds of the way up from Castelfiorentino. There's a park and places to eat in the center, and the main road is a bit off the beaten track.

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Volterra is a beautiful city rich in history and a beautiful road to reach it, only very busy.

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Along the provincial road of Cornocchio, which passes under the homonymous hill and between the natural reserves of Montenero and Castelvecchio, splendid panoramas unfold before you. Cycling here gives you a true Tuscan experience.

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Tower on the square in Gambassi Terme

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BEAUTIFUL VIEW OF THE VALLEY

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Very worth seeing, you have to see it

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Frequently Asked Questions

What kind of terrain can I expect when touring cycling around San Gimignano?

The terrain around San Gimignano is characterized by rolling hills, expansive vineyards, and ancient olive groves. You'll cycle on roads lined with cypress and pine trees, transitioning between open fields and low-lying forests. The elevation changes offer both a challenge and rewarding panoramic views of the Tuscan countryside, including vistas towards Volterra and the Val d'Elsa.

Are there touring cycling routes suitable for beginners or families in San Gimignano?

Yes, while many routes are challenging, the network around San Gimignano offers options for different ability levels. There are 6 easy touring cycling routes available, making it possible for beginners and families to enjoy the scenic Tuscan landscape. The availability of e-bikes also makes the hilly terrain more accessible to a wider range of cyclists.

What are some notable landmarks or attractions I can see along the touring cycling routes?

Many routes pass through picturesque medieval villages and past ancient Romanesque churches. You can explore the historic town of Volterra, or visit the classic medieval stronghold of Monteriggioni Castle. Within San Gimignano itself, you can visit Cistern Square and the Collegiate Church of Santa Maria Assunta. Some routes also offer views of Piazza dei Priori in Volterra.

Are there any circular touring cycling routes around San Gimignano?

Yes, many touring cycling routes around San Gimignano are designed as loops. For example, the San Gimignano — Ring tour is a popular 18.2-mile circular route. Other notable loops include the View of San Gimignano – Piazza dei Priori, Volterra loop and the View of San Gimignano – Monteriggioni Castle loop.

What is the best time of year to go touring cycling in San Gimignano?

The region's pleasant climate makes spring and autumn ideal for touring cycling, offering comfortable temperatures and lush landscapes. While summer can be warm, early mornings or late afternoons are still enjoyable. Always check the weather conditions before heading out.

Can I find cafes or places to stop for refreshments along the cycling routes?

Yes, the region is known for its local produce and wines. Many routes pass through charming villages and along the Vernaccia di San Gimignano wine road, offering opportunities for winery stops and tastings. You'll find cafes and restaurants in towns like San Gimignano, Volterra, and Certaldo Alto, perfect for a break.

What do other touring cyclists say about the routes in San Gimignano?

The touring cycling routes in San Gimignano are highly rated by the komoot community, with an average score of 4.3 stars from over 300 reviews. More than 2,500 touring cyclists have used komoot to explore the varied terrain, often praising the breathtaking views, the challenge of the hills, and the charm of the medieval villages.

Are there any routes that feature waterfalls or natural gorges?

While the primary focus is on the Tuscan landscape and historical sites, there are natural features nearby. You can find highlights like Strolla Stream Waterfalls and the Diborrato Waterfall. For gorges, consider exploring the Botro degli Imbotroni or the Buchi del Diavolo Gorge.

How many touring cycling routes are available around San Gimignano?

There are over 65 touring cycling routes available around San Gimignano, catering to various skill levels. This includes 6 easy routes, 22 moderate routes, and 37 difficult routes, ensuring a diverse range of options for every cyclist.

Is it possible to reach San Gimignano or access routes using public transport?

San Gimignano is accessible by public transport, typically via bus connections from larger cities like Siena or Florence. While direct access to all route starting points might require some planning, reaching the town center by public transport is feasible, allowing you to begin your cycling adventure from there.

Where can I park my car if I'm bringing my own bike to San Gimignano?

San Gimignano has several parking areas located just outside the historic center, which are suitable for visitors. These parking lots offer convenient access to the town and are often used by cyclists starting their tours. It's advisable to check local signage for specific parking regulations and fees.

Are there any specific routes that offer panoramic views of the Tuscan countryside?

Many routes provide stunning panoramic views due to the region's rolling hills. The View of San Gimignano – Piazza dei Priori, Volterra loop is particularly known for traversing scenic hills with vistas towards the historic town of Volterra. The View of San Gimignano – Colle Val d'Elsa Cycle Path loop also offers beautiful views of the Val d'Elsa.

Most popular routes around San Gimignano

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