![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/1575908476/monte-cucco-2.webp)
Challenge of San Gimignanello
A road cycling route starting from Rapolano Terme
Take on the challenge of San Gimignanello
Map
![Map miniature of "Challenge of San Gimignanello" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/rapolano-terme/road/98400.webp)
Embark on a challenging cycling adventure to San Gimignanello near Rapolano Terme. This road route offers diverse terrain and stunning vistas along the way. The highlight of this route is Castiglione d'Orcia, a picturesque village with medieval architecture. With a difficulty rating of 5 and an epicness rating of 4, this route is recommended for experienced cyclists seeking a true challenge.
road
120 km
2203 m
Savage
Route profile
Highlights on the route
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0 km
Start: Rapolano Terme Village centerRapolano Terme: A charming locality with mostly flat routes and thermal baths.
Rapolano Terme is a charming locality situated in the Toscana region of Italy. From a cyclist's perspective, this area offers mostly flat routes with occasional rolling hills, making it ideal for leisurely rides. The locality is known for its thermal baths and wellness centers, providing a relaxing atmosphere for cyclists. Additionally, there are cycling routes that allow riders to explore the scenic countryside and nearby towns. Overall, Rapolano Terme is a tranquil destination for cyclists seeking a blend of cycling and relaxation.8 km
8 km
San GimignanelloCastleSan Gimignanello offers panoramic views of the rolling hills and historic landmarks.
13 km
13 km
Poggio Cannelle449 mPeakPoggio Cannelle is a hill with excellent views of the countryside and a rewarding ascent.
21 km
21 km
TrequandaVillageTrequanda is a picturesque village known for its medieval castle and breathtaking views.
32 km
32 km
Poggio Castellaccio471 mPeakPoggio Castellaccio offers stunning vistas of the surrounding countryside.
55 km
55 km
Castiglione d'OrciaVillageCastiglione d'Orcia is a charming village with medieval architecture and a rich history.
56 km
56 km
Poggio alle Case614 mPeakPoggio alle Case offers captivating panoramas of the hills and valleys of Toscana.
66 km
66 km
Monte Cucco322 mPeakMonte Cucco is a challenging climb with rewarding views of the countryside.
80 km
80 km
MontalcinoTownMontalcino is a charming town famous for its vineyards and the Brunello wine.
89 km
89 km
Poggio Bianco155 mPeakPoggio Bianco offers stunning vistas of the rolling hills and picturesque valleys.
93 km
93 km
BuonconventoVillageBuonconvento is a quaint village known for its medieval architecture and charming streets.
107 km
107 km
Poggio Santa Lucia330 mPeakPoggio Santa Lucia offers panoramic views of the countryside and a chance to rest under the shade of olive trees.
111 km
111 km
AscianoTownAsciano is a charming medieval town known for its historic architecture and stunning views over the Toscana countryside.
120 km
120 km
Finish: Rapolano Terme Village centerRapolano Terme: A charming locality with mostly flat routes and thermal baths.
Cycling routes from Rapolano Terme:
Cycling routes nearby:
![Image of Asciano](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/asciano-5.webp)
![Image of Castelnuovo Berardenga](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/castelnuovo-berardenga-5.webp)
![Image of Monte San Savino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/monte-san-savino-5.webp)
![Image of Lucignano](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/lucignano-3.webp)
![Image of Sinalunga](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/sinalunga-3.webp)
![Image of Marciano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/marciano-della-chiana-5.webp)
![Image of Arbia](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/arbia-4.webp)
![Image of Monteroni d'Arbia](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/monteroni-d-arbia-5.webp)
![Image of Taverne D'Arbia](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/taverne-d-arbia-4.webp)