![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/4952406140/castelnuovo-d-elsa-3.webp)
Rolling Hills and Historic Sites
A road cycling route starting from Castelfiorentino
Journey through Tuscany's picturesque landscapes and medieval towns on this road cycling adventure.
Map
![Map miniature of "Rolling Hills and Historic Sites" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/castelfiorentino/road/360569.webp)
Embark on a memorable road cycling adventure through the enchanting landscapes and rich history of Tuscany. This route offers a combination of rolling hills and moderate climbs, providing a perfect balance of challenge and enjoyment. Visit the charming village of Montaione and immerse yourself in its medieval allure. Explore Poggio al Terraio and discover its historic streets lined with traditional Tuscan buildings. Make a stop in Ghizzano, a hidden gem surrounded by vineyards and olive groves, and marvel at its timeless beauty. As you pedal through Corazzano, Castelnuovo d'Elsa, and Montefoscoli, take in the remarkable architecture and glimpse into the region's fascinating past.
road
65 km
878 m
Tough
Route profile
Highlights on the route
0 km
0 km
Start: Castelfiorentino City centerCastelfiorentino: Picturesque cycling in the Tuscan countryside, Italy
Castelfiorentino is a charming town located in the Toscana region of Italy. The area offers a range of cycling opportunities with its winding roads and rolling hills. Cyclists can explore the picturesque Tuscan countryside and pass through olive groves, vineyards, and historic villages. The nearby town of San Gimignano with its medieval towers is a must-visit for tourists. Castelfiorentino's stunning landscapes and cultural attractions make it an excellent choice for cyclists interested in combining sport and tourism.9 km
9 km
MontaioneVillage10 km
10 km
Poggio al Terraio352 mPeakExperience the medieval charm of Poggio al Terraio, with its narrow streets and traditional Tuscan buildings.
27 km
27 km
GhizzanoHamletDiscover the hidden jewel of Ghizzano, a small village surrounded by vineyards that offers breathtaking views at every turn.
33 km
33 km
MontefoscoliHamletImmerse yourself in the rich medieval history of Montefoscoli, as you explore its well-preserved buildings and charming streets.
51 km
51 km
CorazzanoVillageTake a stroll through Corazzano and admire its picturesque streets and impressive medieval castle.
58 km
58 km
Castelnuovo d'ElsaHamletVisit the medieval village of Castelnuovo d'Elsa and witness the stunning panoramic views from its hilltop location.
65 km
65 km
Finish: Castelfiorentino City centerCastelfiorentino: Picturesque cycling in the Tuscan countryside, Italy
Cycling routes nearby:
![Image of Montaione](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montaione-2.webp)
![Image of Gambassi Terme](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/gambassi-terme-5.webp)
![Image of Certaldo](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/certaldo-3.webp)
![Image of Montespertoli](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montespertoli-4.webp)
![Image of Pozzale-Case Nuove](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/pozzale-case-nuove-5.webp)
![Image of Empoli](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/empoli-4.webp)
![Image of Spicchio-Sovigliana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/spicchio-sovigliana-5.webp)
![Image of Montelupo Fiorentino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montelupo-fiorentino-3.webp)
![Image of San Miniato Basso](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/san-miniato-basso-3.webp)