![Cover image](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/castiglion-fiorentino-4.webp)
Uncover Tuscan treasures on tranquil cycling routes.
Cycling routes from Castiglion Fiorentino
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.
![Map miniature of "Castiglion Fiorentino - Passignano sul Trasimeno" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/castiglion-fiorentino/gravel/92702.webp)
Discover the picturesque towns along Lake Trasimeno on this gravel cycling route.
This scenic 77-kilometer gravel route takes you from Castiglion Fiorentino to Passignano sul Trasimeno, passing through beautiful Tuscan and Umbrian landscapes. Along the way, you'll enjoy stunning views of Lake Trasimeno and encounter charming towns like Camucia and Montecchio Vesponi. The route includes a total ascent of 419 meters, making it suitable for moderately experienced cyclists. Get ready to experience the natural beauty and cultural richness of the area through this rewarding cycling adventure.
![Map miniature of "The Panoramic Trek" 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/92701.webp)
Discover breathtaking natural beauty and medieval castles on this scenic cycling route near Castiglion Fiorentino.
Embark on a journey through picturesque landscapes and cultural landmarks, as you cycle along this 111 km route. With a moderate ascent of 1602 meters, this route is perfect for experienced cyclists looking for a challenging adventure. Explore the charming town of Castiglion Fiorentino and enjoy highlights such as the impressive Belvedere Rossano Naldi and the stunning Monte Ferrato. Experience the rich history and stunning landscapes of Talla, Rassina, Subbiano, and Mammi.
The Valiano Loop
![Map miniature of "The Valiano Loop" 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/92646.webp)
Experience the picturesque landscapes of Valiano and the surrounding areas on this road cycling route near Castiglion Fiorentino.
Discover the beauty of Valiano and its surrounding areas on this 89 km road cycling route. With a moderate ascent of 766 meters, this route is perfect for cyclists seeking a challenging adventure. Start your journey in Castiglion Fiorentino and explore highlights such as the stunning Valiano and the enchanting I Poggi. Visit the small town of Sinalunga and enjoy the picturesque landscapes of Marciano della Chiana and Mortelle.
![Map miniature of "Castiglion Fiorentino - Pergognano Gravel Loop" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/castiglion-fiorentino/gravel/92715.webp)
Take on a challenging gravel loop exploring the hills and countryside near Castiglion Fiorentino.
This 46-kilometer gravel loop starting near Castiglion Fiorentino takes you through diverse landscapes and historic villages. With an ascent of 1508 meters, the route offers a challenging adventure suitable for experienced riders. Along the way, you'll conquer peaks like Monte Corneta and Monte Dogana, discover rural communities like Poggio delle Cerchiaie, and enjoy panoramic views from Pergognano. Get ready to challenge yourself and immerse in the captivating scenery and cultural heritage of Tuscany on this memorable gravel journey.
![Map miniature of "The Tranquil Trail" 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/92617.webp)
Escape the crowds and indulge in the peaceful countryside on this 47 km road cycling route near Castiglion Fiorentino.
Experience the beauty of the countryside as you meander through the peaceful landscapes on this 47 km road cycling route. With a manageable ascent of 350 meters, this route is perfect for cyclists of all levels. Discover the charming Belvedere Rossano Naldi and enjoy highlights such as Fonte del Mazza and Montecchio. Immerse yourself in the small town charm of Foiano della Chiana and Manciano.
![Map miniature of "Castiglion Fiorentino - Cortona Gravel 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/gravel/92699.webp)
Explore the Tuscany countryside on this adventurous gravel route from Castiglion Fiorentino to Cortona.
This 72-kilometer gravel adventure leads you from Castiglion Fiorentino to Cortona, showcasing the beautiful landscapes and cultural richness of the region. With an ascent of 527 meters, the route offers a moderate challenge suitable for experienced cyclists. Along the way, you'll pass through the charming town of Cortona, known for its ancient walls, historic center, and captivating views. Take advantage of the picturesque countryside and immerse yourself in the authentic Tuscan atmosphere as you cycle through this captivating journey.
![Map miniature of "Castiglion Fiorentino - Cortona Epic Gravel Ride" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/castiglion-fiorentino/gravel/92733.webp)
Get ready for an epic gravel adventure from Castiglion Fiorentino to Cortona.
This challenging 78-kilometer gravel ride takes you from Castiglion Fiorentino to Cortona, passing through rugged terrains and picturesque landscapes. With a total ascent of 2328 meters, this route is ideal for experienced riders seeking a thrilling adventure. Along the way, you'll conquer impressive peaks like Monte Corneta and Passo della Cerventosa, and discover hidden gems like Poggio Montanina and Pievuccia. Enjoy the stunning panoramic views and immerse yourself in the natural beauty of Tuscany throughout this epic cycling journey.
The Hillside Adventure
![Map miniature of "The Hillside 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/92637.webp)
Embark on an exciting cycling adventure through the scenic hillsides near Castiglion Fiorentino.
Get ready for an adventurous ride through the beautiful hillsides on this 88 km road cycling route. With a moderate ascent of 952 meters, this route is suitable for cyclists who enjoy a challenge. Explore the historic town of Castiglion Fiorentino and discover highlights such as the renowned Belvedere Rossano Naldi and the charming Monte San Savino. Immerse yourself in the fascinating towns of Poggio Muricci, Poggio Santa Lucia, and Monte Acuto.
![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)
Embark on a thrilling cycling experience through the hilltops near Castiglion Fiorentino.
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.
![Map miniature of "Belvedere Rossano Naldi Loop" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/castiglion-fiorentino/gravel/92629.webp)
Embark on a short but adventurous gravel loop exploring the hills near Belvedere Rossano Naldi.
This 41-kilometer gravel loop starting near Belvedere Rossano Naldi is perfect for those seeking a shorter but exciting off-road cycling experience. With an ascent of 347 meters, the route provides a moderate challenge suitable for intermediate cyclists. You'll encounter picturesque landscapes, quaint villages like Tegoleto, and natural wonders like Mortelle. Take in the beautiful views and serenity of the countryside as you navigate this scenic loop.
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)
Nearby regions:
![Image of Corse](https://images.tarmacs.app/cycling-routes/covers/france/corse/santa-maria-di-lota-3.webp)
![Image of Piemonte](https://images.tarmacs.app/cycling-routes/covers/italy/piemonte/vicoforte-3.webp)
![Image of Lombardia](https://images.tarmacs.app/cycling-routes/covers/italy/lombardia/pandino-4.webp)
![Image of Veneto](https://images.tarmacs.app/cycling-routes/covers/italy/veneto/monselice-5.webp)
![Image of Emilia-Romagna](https://images.tarmacs.app/cycling-routes/covers/italy/emilia-romagna/castenaso-5.webp)
![Image of Umbria](https://images.tarmacs.app/cycling-routes/covers/italy/umbria/santa-maria-degli-angeli-1.webp)
![Image of Marche](https://images.tarmacs.app/cycling-routes/covers/italy/marche/torre-san-patrizio-4.webp)