![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/617533900/cortona-1.webp)
The Hilltop Adventure
A road cycling route starting from Castiglion Fiorentino
Embark on a thrilling cycling experience through the hilltops near Castiglion Fiorentino.
Map
![Map miniature of "The Hilltop Adventure" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/castiglion-fiorentino/road/92675.webp)
Prepare for an adventure-filled journey through the hilltops on this 107 km road cycling route. With a challenging ascent of 1524 meters, this route is recommended for experienced cyclists looking for a thrilling ride. Explore the historic town of Castiglion Fiorentino and discover highlights such as Poggio della Fornace and Monte Gualandro. Immerse yourself in the charming towns of Badia Petroia, Montecastelli, and Cortona.
road
107 km
1524 m
Savage
Route profile
Highlights on the route
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Start: Castiglion Fiorentino City centerCastiglion Fiorentino: Uncover Tuscan treasures on tranquil cycling routes.
Castiglion Fiorentino is a charming town in the Tuscany region of Italy that provides a delightful cycling experience. The area surrounding Castiglion Fiorentino offers a mix of quiet country roads and rolling hills, perfect for road and gravel cyclists. The rides are generally moderate, with occasional short climbs to keep things interesting. The town itself features several historical sites, including its medieval walls and the Church of Sant'Angelo. Famous cycling climbs such as the Monte Lignano are also easily accessible from Castiglion Fiorentino. Overall, Castiglion Fiorentino is a hidden gem suitable for cyclists looking to immerse themselves in Tuscany's beauty.0 km
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Castiglion FiorentinoTownVisit the historic town of Castiglion Fiorentino and immerse yourself in its cultural heritage.
12 km
12 km
Poggio della Fornace608 mPeakMarvel at the majestic Poggio della Fornace and enjoy its stunning surroundings.
29 km
29 km
Badia PetroiaHamletStop by the beautiful Badia Petroia and admire its architectural beauty.
40 km
40 km
MontecastelliVillageExperience the charming town of Montecastelli and delight in its tranquil setting.
52 km
52 km
Monte Valcinella692 mPeakDiscover the breathtaking beauty of Monte Valcinella and take in its scenic landscapes.
64 km
64 km
Colle Sassi Bianchi707 mPeakVisit the fascinating Colle Sassi Bianchi and immerse yourself in its rich history.
66 km
66 km
Castel RigoneVillageExplore the enchanting town of Castel Rigone and enjoy its picturesque surroundings.
81 km
81 km
Tuoro sul TrasimenoVillageTake a break at Tuoro sul Trasimeno and admire the stunning views of Lake Trasimeno.
85 km
85 km
Monte Gualandro441 mPeakMarvel at the grandeur of Monte Gualandro and enjoy the breathtaking view.
94 km
94 km
CortonaTownVisit the charming town of Cortona and experience its rich history and culture.
107 km
107 km
Belvedere Rossano NaldiViewpointEnjoy panoramic views from the Belvedere Rossano Naldi.
107 km
107 km
Finish: Castiglion Fiorentino City centerCastiglion Fiorentino: Uncover Tuscan treasures on tranquil cycling routes.
Cycling routes from Castiglion Fiorentino:
The Tranquil Trail Belvedere Rossano Naldi Loop The Hillside Adventure The Valiano Loop The Hilltop Adventure Castiglion Fiorentino - Cortona Gravel Adventure The Panoramic Trek Castiglion Fiorentino - Passignano sul Trasimeno Castiglion Fiorentino - Pergognano Gravel Loop Castiglion Fiorentino - Cortona Epic Gravel Ride
Cycling routes nearby:
![Image of Cortona](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/cortona-5.webp)
![Image of Marciano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/marciano-della-chiana-5.webp)
![Image of Pieve al Toppo](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/pieve-al-toppo-5.webp)
![Image of Foiano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/foiano-della-chiana-5.webp)
![Image of Arezzo](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/arezzo-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 Terontola](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/terontola-5.webp)
![Image of Bettolle](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/bettolle-4.webp)