![Cover image](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/cortona-5.webp)
Conquer epic climbs and soak up historic charm in Cortona.
Cycling routes from Cortona
Cortona is a stunning town located in the Tuscany region of Italy. With its hilltop location and panoramic views, Cortona offers a remarkable setting for road and gravel cyclists. The surrounding countryside features challenging climbs, winding roads, and idyllic landscapes straight out of a postcard. Famous climbs like Monte Sant'Egidio and Monte San Michele are within reach for those seeking an extra challenge. Cortona itself is abundant in history and cultural heritage, with its ancient walls, Etruscan ruins, and charming streets. If you're looking for a remarkable cycling destination with awe-inspiring scenery, Cortona should be on your list.
![Map miniature of "From Cortona to Arezzo and Castiglion Fiorentino" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/road/92694.webp)
Embark on a scenic road cycling route from Cortona to the historic towns of Arezzo and Castiglion Fiorentino
This road cycling route takes you through the scenic Tuscan countryside, passing through the towns of Arezzo and Castiglion Fiorentino. With a total distance of 109km and an ascent of 1490m, this route provides a challenging ride for well-trained amateurs. Along the way, you'll be treated to breathtaking views of the rolling hills and vineyards. The highlights of this route include Badicorte, Poggio Scopicci, Ponticino, Arezzo, Belvedere Rossano Naldi, Castiglion Fiorentino, and Camucia.
![Map miniature of "A Short and Sweet Cortona Adventure" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/road/92684.webp)
Experience the beauty of Cortona in a short ride
Enjoy a leisurely 38-km road cycling route that showcases the beauty of Cortona. With 351 meters of ascent, this short and sweet journey allows you to experience the breathtaking landscapes surrounding the town. Pedal through picturesque villages, rolling hills, and vineyards, and uncover the charm of Cortona at a relaxed pace.
![Map miniature of "From Cortona to Montepulciano and Trequanda" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/road/92642.webp)
Explore the charming towns of Montepulciano and Trequanda on this road cycling route from Cortona
This road cycling route takes you through idyllic Tuscan countryside, passing through picturesque towns such as Montepulciano and Trequanda. With a total distance of 98km and an ascent of 1256m, this route provides a moderately challenging ride, suitable for well-trained amateurs. Along the way, you'll have the opportunity to soak in the beauty of the Italian countryside, with vineyards and olive groves stretching as far as the eye can see. The highlights of this route include Camucia, Valiano, Poggio San Pietro, Trequanda, Poggio del Castagnolo, Foiano della Chiana, and Fratta-Santa Caterina.
![Map miniature of "Mountains and Gravel in Cortona" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/gravel/92667.webp)
Conquer challenging gravel climbs near Cortona
Prepare for breathtaking scenery and exhilarating gravel climbs on this 99-km route near Cortona. With a total ascent of 2867 meters, you'll be rewarded with stunning views at every turn. Explore rugged mountain peaks, remote villages, and ancient ruins as you tackle this epic cycling adventure.
![Map miniature of "The Montecchio Gravel Adventure" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/gravel/92663.webp)
Explore the charming village of Montecchio along this scenic gravel route.
Embark on a picturesque gravel adventure starting near Cortona, Toscana. This 56km route offers stunning views and takes you through several charming towns.
Road Tales of Cortona
![Map miniature of "Road Tales of Cortona" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/road/92652.webp)
Embark on an unforgettable road cycling journey near Cortona
Uncover the hidden gems of Tuscany on this 98-km road cycling route around Cortona. With 1071 meters of ascent and a mix of scenic landscapes, charming towns, and historic sites, this route promises an enriching experience. Immerse yourself in the tranquil countryside of Tuscany and explore the rich cultural heritage of the region.
![Map miniature of "Gravelful Cortona Loop" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/gravel/92657.webp)
A thrilling gravel adventure near Cortona
Experience the exhilaration of gravel cycling in the beautiful countryside surrounding Cortona. This route takes you on a 63-km ride with 2029 meters of ascent, showcasing some of the most picturesque landscapes in Tuscany. Get ready to explore ancient fortresses, majestic mountains, and charming villages along the way.
![Map miniature of "The Chianti Road Challenge" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/road/92668.webp)
Embark on a challenging road route through the iconic Chianti region.
Prepare for an exhilarating road cycling adventure near Cortona, Toscana. This 103km route will challenge your climbing abilities and reward you with stunning views of the famous Chianti vineyards.
The Valiano Gravel Experience
![Map miniature of "The Valiano Gravel Experience" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/gravel/92641.webp)
Embark on a gravel journey and explore the charming village of Valiano.
Embark on a gravel adventure near Cortona, Toscana, and make the stunning village of Valiano your focus point. This 64km route takes you through scenic countryside and offers breathtaking views.
![Map miniature of "The Scenic Mountain Gravel Route" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/cortona/gravel/92639.webp)
Embark on a thrilling gravel climb and enjoy breathtaking mountain views.
Discover the beauty of the Tuscan mountains near Cortona, Toscana through this challenging 31km gravel route. Get ready for steep climbs and jaw-dropping panoramic vistas along the way.
Cycling routes nearby:
![Image of Terontola](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/terontola-5.webp)
![Image of Castiglion Fiorentino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/castiglion-fiorentino-4.webp)
![Image of Tuoro sul Trasimeno](https://images.tarmacs.app/cycling-routes/covers/italy/umbria/tuoro-sul-trasimeno-5.webp)
![Image of Foiano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/foiano-della-chiana-5.webp)
![Image of Passignano sul Trasimeno](https://images.tarmacs.app/cycling-routes/covers/italy/umbria/passignano-sul-trasimeno-3.webp)
![Image of Marciano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/marciano-della-chiana-5.webp)
![Image of Bettolle](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/bettolle-4.webp)
![Image of Castiglione del Lago](https://images.tarmacs.app/cycling-routes/covers/italy/umbria/castiglione-del-lago-5.webp)
![Image of Montepulciano Stazione](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montepulciano-stazione-4.webp)
Nearby regions:
![Image of Corse](https://images.tarmacs.app/cycling-routes/covers/france/corse/furiani-2.webp)
![Image of Piemonte](https://images.tarmacs.app/cycling-routes/covers/italy/piemonte/borgaro-torinese-2.webp)
![Image of Liguria](https://images.tarmacs.app/cycling-routes/covers/italy/liguria/quiliano-2.webp)
![Image of Lombardia](https://images.tarmacs.app/cycling-routes/covers/italy/lombardia/sartirana-lomellina-3.webp)
![Image of Veneto](https://images.tarmacs.app/cycling-routes/covers/italy/veneto/santa-maria-maddalena-3.webp)
![Image of Emilia-Romagna](https://images.tarmacs.app/cycling-routes/covers/italy/emilia-romagna/altedo-5.webp)
![Image of Umbria](https://images.tarmacs.app/cycling-routes/covers/italy/umbria/castel-giorgio-1.webp)
![Image of Lazio](https://images.tarmacs.app/cycling-routes/covers/italy/lazio/aquino-5.webp)