![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/617536790/casole-d-elsa-1.webp)
Road Cycling Adventure around San Gimignano
A road cycling route starting from San Gimignano
Embark on an epic road cycling adventure around San Gimignano, taking in the breathtaking landscapes and historic sites along the way
Map
![Map miniature of "Road Cycling Adventure around San Gimignano" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/san-gimignano/road/140523.webp)
Experience the beauty and history of San Gimignano on this road cycling adventure. The route takes you through rolling hills, charming villages, and iconic landmarks, offering a mix of challenging climbs and fast descents. With highlights including the medieval town of Monteriggioni, Poggio Imperiale, Poggiali, Poggio della Castellaccia, Casole d'Elsa, Borgatello, and La Rocca, this tour provides a truly immersive experience of the region. The difficulty level is moderate to challenging, making it suitable for well-trained amateur cyclists. Don't miss the opportunity to discover the rich cultural heritage and stunning landscapes of San Gimignano and its surroundings.
road
92 km
1033 m
Tough
Route profile
Highlights on the route
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Start: San Gimignano Village centerSan Gimignano: Italian Cycling Haven
San Gimignano, located in Toscana, Italy, is a cyclist's dream destination. With its rolling hills and picturesque landscapes, San Gimignano offers a variety of routes for road and gravel cyclists to explore. The region is known for its vineyards and olive groves, making for a beautiful backdrop during rides. Cyclists can enjoy the challenge of climbing the nearby Passo di Montecucco or take a leisurely ride through the countryside, stopping to sample local wines along the way. San Gimignano is a must-visit destination for cyclists looking for both challenging climbs and stunning scenery.0 km
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San GimignanoAttractionSan Gimignano, with its iconic medieval towers, is a must-visit destination known for its unique architecture and rich history.
11 km
11 km
Poggio Imperiale199 mPeakPoggio Imperiale offers panoramic views of the Tuscan countryside and vineyards.
24 km
24 km
MonteriggioniVillageMonteriggioni, a fortified medieval town, will take you back in time with its intact walls and narrow streets.
32 km
32 km
Poggiali301 mPeakPoggiali is a challenging climb that rewards you with stunning vistas of rolling hills and olive groves.
42 km
42 km
AmpugnanoVillageAmpugnano is a picturesque village with traditional Tuscan architecture and charming cafes.
46 km
46 km
Poggio della Castellaccia325 mPeakPoggio della Castellaccia offers panoramic views of the surrounding countryside and vineyards.
58 km
58 km
Poggio a Gattero420 mPeakPoggio a Gattero provides breathtaking vistas of the Tuscan landscapes and vineyards.
69 km
69 km
Casole d'ElsaVillageCasole d'Elsa is a charming hilltop village with narrow streets and beautiful views.
82 km
82 km
BorgatelloVillageBorgatello is a quaint village known for its hospitality and traditional Tuscan cuisine.
91 km
91 km
La RoccaViewpointLa Rocca is a historic fortress offering panoramic views of the Val d'Elsa region.
92 km
92 km
Finish: San Gimignano Village centerSan Gimignano: Italian Cycling Haven
Cycling routes from San Gimignano:
San Gimignano Road Loop Chianti Gravel Adventure Monteriggioni Loop Chianti Classic From San Gimignano to Greve in Chianti San Gimignano Scenic Route Historical Gravel Ride San Gimignano Gravel Loop Off-Road Adventure Gravel Escape Gravel Tour through San Gimignano Countryside Road Cycling Adventure around San Gimignano
Cycling routes nearby:
![Image of Certaldo](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/certaldo-3.webp)
![Image of Gambassi Terme](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/gambassi-terme-5.webp)
![Image of Poggibonsi](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/poggibonsi-1.webp)
![Image of Colle di Val d'Elsa](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/colle-di-val-d-elsa-4.webp)
![Image of Montaione](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montaione-2.webp)
![Image of Tavarnelle Val di Pesa](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/tavarnelle-val-di-pesa-5.webp)
![Image of Volterra](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/volterra-4.webp)
![Image of Castelfiorentino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/castelfiorentino-4.webp)