![Cover image](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/roccastrada-3.webp)
Embark on a cycling adventure amidst the scenic beauty of Roccastrada, Toscana.
Cycling routes from Roccastrada
Roccastrada, located in Toscana, Italy, offers exceptional road and gravel cycling opportunities. The town is surrounded by lush countryside and vineyards, providing cyclists with breathtaking views throughout their rides. Roccastrada is also a gateway to the famous Monte Labbro climb, known for its challenging gradients and stunning vistas at the top. With its idyllic scenery and notable cycling climbs, Roccastrada is a prime destination for cyclists of all levels.
![Map miniature of "Epic Road Cycling Route around Roccastrada" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/road/95991.webp)
Experience the Tuscan countryside on this challenging road cycling route
This road cycling route starting near Roccastrada takes you through the beautiful Tuscan countryside, offering breathtaking views of rolling hills, vineyards, and charming medieval villages. With a total distance of 162 kilometers and an ascent of 2550 meters, this route is perfect for experienced cyclists looking for a challenge. The difficulty level of this route is rated 4 out of 5, making it suitable for very well-trained amateurs. Along the way, you will encounter several highlights, each with its own unique features and attractions.
Roccastrada Gravel Tour
![Map miniature of "Roccastrada Gravel Tour" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/gravel/93304.webp)
Embark on a thrilling 46 km gravel tour from Roccastrada.
Hop on your gravel bike and embark on an exhilarating 46 km tour starting from Roccastrada. With a moderate ascent of 890 meters, this route takes you through the charming highlights of Poggio di Casetta and the beautiful Poggio di Femmina Morta. Explore the historic village of Civitella Marittima before heading towards the vibrant town of Paganico. Admire the natural beauty of Poggetto di Balucante and Rocca al Forno before concluding your journey back in Roccastrada. This exciting gravel tour offers a perfect mix of scenic vistas and cultural discoveries.
![Map miniature of "Castiglione della Pescaia and Montalcino Road Loop" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/road/95897.webp)
Discover the seaside charm of Castiglione della Pescaia and the wine region of Montalcino on this road loop
Immerse yourself in the beauty of the Tuscan coast and wine country on this road cycling loop near Roccastrada. Starting in Roccastrada, the route passes through towns such as Poggio Oliveto, Poggio Romano, Braccagni, Castiglione della Pescaia, Pian d'Alma, Poggetto degli Ulivi, Poggio Tondo, Puntone di Scarlino, Scarlino Scalo, Poggio della Fornace, Sassoforte, and Sassofortino, before returning to Roccastrada. The route features a total ascent of 1035 meters over a distance of 121 kilometers. It is suitable for intermediate-level cyclists. Highlights along the route include Castiglione della Pescaia, a picturesque seaside town known for its sandy beaches and crystal-clear waters. With a score of 4, Poggio Oliveto offers panoramic views and a scenic cycling route through vineyards and olive groves. Poggio Romano, with a score of 3, is a peaceful village surrounded by beautiful countryside. Overall, this road route provides a diverse mix of coastal and countryside scenery, allowing you to experience both the charm of the Tuscan coast and the world-famous wines of Montalcino.
![Map miniature of "The Roccastrada Climbing Challenge" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/road/140040.webp)
Climb through beautiful Tuscan landscapes and rural villages to test your endurance.
This challenging road cycling route starting near Roccastrada will take you through some of the most picturesque landscapes in Tuscany. With a total ascent of 1247 meters and a distance of 129 kilometers, this ride is ideal for well-trained amateurs looking for a real challenge. The route will pass through the quaint villages of Paganico, Campagnatico, and Arcille before reaching the iconic Poggio del Cimbello climb. From there, riders will be rewarded with stunning views of the countryside as they make their way towards Grosseto. The final stretch includes the beautiful towns of Braccagni and Montiano, before culminating in the triumphant return to Roccastrada.
![Map miniature of "Tuscan Gravel Adventure" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/gravel/93307.webp)
Embark on a 101 km gravel adventure through the stunning landscapes of Toscana.
Embark on a breathtaking 101 km gravel adventure through the beautiful landscapes of Toscana. With an ascent of 1,053 meters, this route promises exhilarating climbs and awe-inspiring views. Highlights of this adventure include the majestic Monte Leoni, the charming Poggio Mosconcino, and the vibrant city of Grosseto. Don't miss the idyllic coastal town of Marina di Grosseto before heading towards the historic Buriano. Experience the thrill of conquering Monte Lattaia and marvel at the ancient Cripta di San Salvatore a Giugnano. This Tuscan gravel adventure offers a perfect blend of natural wonders and cultural gems.
![Map miniature of "Roccastrada Road Warrior" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/road/95843.webp)
Conquer the challenging 123 km road route starting from Roccastrada.
For road cycling enthusiasts, this challenging 123 km route starting from Roccastrada is a true when it comes to testing your limits. With an ascent of 2,064 meters, this ride takes you through notable highlights such as Poggio alle Capanne and the charming town of Monticiano. Experience the exhilarating Poggio La Sassa and marvel at the historic beauty of Murlo. Conquer the iconic Poggio Grilli and explore the enchanting town of Buonconvento. Don't miss the opportunity to visit the renowned wine region of Montalcino before conquering the stunning Poggio Civitella. Finish your journey with breathtaking views from Poggio all'Oro and Borgo Santa Rita. This road warrior route in Toscana is not for the faint-hearted.
![Map miniature of "Roccastrada Gravel Adventura" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/gravel/93289.webp)
Explore the diverse landscapes around Roccastrada on this 99 km gravel adventure.
Discover the picturesque countryside surrounding Roccastrada on this challenging yet rewarding 99 km gravel route. With a total ascent of 2,081 meters, this ride takes you through various highlights such as Monte Altarello, the enchanting village of Casale di Pari, and the stunning Poggio Chiari. The route also includes iconic spots like Castelnuovo Tancredi and Poggio Cornato, which offer breathtaking views. Experience the beauty of Collalto and Borgo Santa Rita before reaching Cassero Senese, and don't miss the unique Poggio alle Tagliate and Poggio la Pigna. Get ready for an epic adventure in Toscana's cycling paradise!
Roccastrada Road Escape
![Map miniature of "Roccastrada Road Escape" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/road/95850.webp)
Embark on a picturesque 110 km road escape starting from Roccastrada.
Indulge in a picturesque road escape starting from Roccastrada. This 110 km route with an ascent of 1,804 meters takes you through the spectacular countryside of Toscana. Discover the hidden gem of Poggio San Niccolò and immerse yourself in the charm of Civitella Marittima. Visit the scenic Borgo Santa Rita before conquering the challenging slopes of Poggio Mai. Admire the beauty of Stribugliano and enjoy the panoramic views from Poggio delle Caldaie. Explore the historic town of Baccinello before savoring the serenity of Poggio dell'Ulivastra. Pass through the idyllic town of Campagnatico and embrace the fantastic landscapes. Conclude your road escape by conquering the vibrant city of Paganico and capturing the beauty of Poggio del Cimbello.
![Map miniature of "Paganico and Campagnatico Road Loop" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/road/95859.webp)
Explore the scenic towns of Pantomima and Campganatico on this road loop
Experience the beauty of the Tuscan countryside on this road cycling route near Roccastrada. Starting in Roccastrada, the loop takes you through charming towns such as Poggio Castello, Paganico, Campagnatico, Arcille, Istia d'Ombrone, Poggio Mosconcino, Braccagni, Poggio Romano, Poggio Oliveto, and back to Roccastrada. The route offers a total ascent of 997 meters over a distance of 90 kilometers. It is suitable for well-trained amateur cyclists. Highlights along the route include Poggio Castello and Poggio Oliveto, both offering beautiful views of the surrounding countryside. With a score of 4, Paganico is an attractive spot with its historic architecture and charming atmosphere. Overall, this road route provides a scenic and enjoyable cycling experience, allowing you to explore the cultural heritage and natural landscapes of Tuscany.
![Map miniature of "Scenic Gravel Cycling Route near Roccastrada" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/roccastrada/gravel/96005.webp)
Embark on an exhilarating gravel cycling adventure through the picturesque Tuscan countryside
Explore the stunning natural landscapes of the Tuscan countryside on this gravel cycling route starting near Roccastrada. With a distance of 128 kilometers and an ascent of 2985 meters, this route caters to experienced gravel cyclists seeking a challenging and rewarding adventure. Rated at difficulty level 5, this ride is suitable for very well-trained amateurs looking for an epic experience. Along the way, you will encounter various highlights, each offering its own distinct charm and beauty.
Cycling routes nearby:
![Image of Ribolla](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/ribolla-5.webp)
![Image of Bagno Roselle](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/bagno-roselle-5.webp)
![Image of Massa Marittima](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/massa-marittima-4.webp)
![Image of Montalcino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montalcino-4.webp)
![Image of Rosia](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/rosia-3.webp)
![Image of Grosseto](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/grosseto-2.webp)
![Image of Scarlino Scalo](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/scarlino-scalo-5.webp)
![Image of Buonconvento](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/buonconvento-4.webp)
![Image of Castelnuovo di Val di Cecina](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/castelnuovo-di-val-di-cecina-4.webp)
Nearby regions:
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![Image of Piemonte](https://images.tarmacs.app/cycling-routes/covers/italy/piemonte/coazze-3.webp)
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![Image of Lombardia](https://images.tarmacs.app/cycling-routes/covers/italy/lombardia/zorlesco-4.webp)
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![Image of Umbria](https://images.tarmacs.app/cycling-routes/covers/italy/umbria/assisi-5.webp)
![Image of Marche](https://images.tarmacs.app/cycling-routes/covers/italy/marche/grottammare-5.webp)
![Image of Lazio](https://images.tarmacs.app/cycling-routes/covers/italy/lazio/lariano-3.webp)