![Cover image](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montepulciano-5.webp)
A famous town with challenging climbs and rolling hills.
Cycling routes from Montepulciano
Montepulciano is a famous locality located in the Toscana region of Italy. From a cyclist's perspective, this town offers a mix of challenging climbs and rolling hills, making it suitable for experienced riders. The nearby climb up to Montepulciano provides breathtaking views of the surrounding vineyards and scenery. The roads in this area are generally well-maintained, making it suitable for road cycling. Montepulciano also offers bike rentals and guided cycling tours for visitors. Overall, this locality is a fantastic destination for cyclists looking for challenging climbs and stunning landscapes.
![Map miniature of "Challenging Road Cycling Loop to Cortona" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/road/98354.webp)
Embark on a challenging road cycling adventure to Cortona.
This demanding road cycling loop takes you through challenging climbs, picturesque towns, and breathtaking landscapes. Covering a distance of 92 kilometers and with a significant ascent, this route is recommended for experienced cyclists. Enjoy panoramic views, test your endurance, and discover the beauty of the Tuscan countryside.
![Map miniature of "Gravel Loop Montepulciano and Surroundings" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/gravel/98341.webp)
Discover the quaint villages and beautiful countryside around Montepulciano on this gravel route.
This gravel loop takes you through the charming villages and picturesque countryside surrounding Montepulciano. Pedal along rolling hills, passing vineyards, olive groves, and scenic landscapes. With a moderate difficulty level and several highlights to discover along the way, this route offers a great opportunity to explore the Tuscany region.
![Map miniature of "Montepulciano Round-Trip Cycling" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/road/140391.webp)
Experience the beauty of Tuscany on this challenging road cycling route starting in Montepulciano.
Get ready to climb and descend through the breathtaking Tuscan countryside on this epic round-trip cycling adventure. Montepulciano, known for its fine wines and Renaissance architecture, serves as the starting point for this scenic route. Prepare to be amazed by picturesque villages like Montefollonico, Piazza di Siena, and Lucignano, each offering their own unique charms. As you pedal through rolling hills and vineyards, you'll encounter the medieval towns of Monte San Savino and Poggio Scopicci, showcasing history and architectural beauty. Don't miss the opportunity to visit the Fattoria, a charming farm offering a taste of Tuscan agriculture. Conclude your journey with a stop at the stunning Ascianello, an ancient fortress with panoramic views.
![Map miniature of "Montepulciano - Sant'Albino - Montepulciano" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/gravel/98346.webp)
Embark on a moderate gravel cycling route from Montepulciano to Sant'Albino, passing by beautiful spots like Castiglioncello del Trinoro and Sarteano.
This moderate gravel cycling route takes you from Montepulciano to Sant'Albino and back, passing through picturesque landscapes, charming villages, and hidden gems. With a moderate difficulty level and plenty of highlights to discover, this route offers a rewarding cycling experience.
![Map miniature of "Montepulciano - Poggio Bianco - Montepulciano" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/gravel/98330.webp)
Embark on a gravel cycling adventure to Poggio Bianco, enjoying picturesque landscapes and sights like Petroio and Rigomagno along the way.
This gravel cycling route takes you from Montepulciano to Poggio Bianco and back, with scenic landscapes, charming towns, and unique highlights along the way. With a moderate difficulty level and a range of attractions, this route is ideal for gravel cyclists seeking a diverse adventure.
![Map miniature of "Cycling Adventure to Montalcino and Sant'Angelo Scalo" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/road/98347.webp)
Embark on a challenging cycling adventure to Montalcino and Sant'Angelo Scalo.
This challenging cycling adventure takes you through the stunning landscapes of the Val d'Orcia and Montalcino. Covering a distance of 140 kilometers with significant climbing, this route is recommended for experienced cyclists seeking a true challenge. Explore charming villages, vineyards, and iconic landmarks along the way, experiencing the beauty of the Tuscany region.
![Map miniature of "Short Gravel Adventure to Poggio della Cava" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/gravel/98335.webp)
Embark on a short, yet adventurous gravel cycling journey to Poggio della Cava.
This relatively short gravel route takes you to the charming village of Poggio della Cava. With a total distance of 33 kilometers and moderate difficulty level, it is perfect for a quick cycling adventure. Ride through olive groves, vineyards, and rolling hills, enjoying the scenic beauty of the Tuscany region.
![Map miniature of "Montepulciano - Pienza - Montepulciano" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/road/98350.webp)
Explore the charming towns of Monticchiello, San Quirico d'Orcia, and Montisi on this road cycling route.
This scenic road cycling route takes you from Montepulciano to Pienza and back, passing through picturesque towns like Monticchiello, San Quirico d'Orcia, and Montisi. The route offers beautiful views of the countryside and features several highlights worth exploring along the way. With a moderate difficulty level and a range of attractions, this route is a great option for cyclists of varying abilities.
![Map miniature of "Scenic Road Cycling Route to Chianciano Terme" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/road/98332.webp)
Embark on a scenic road cycling adventure to Chianciano Terme.
This road cycling route takes you from Montepulciano to Chianciano Terme, offering stunning views of the Tuscan countryside. With a moderate difficulty level, this 75-kilometer route is suitable for well-trained amateurs. Explore quaint villages, rolling hills, and historic landmarks along the way. The route offers a perfect combination of physical challenge and breathtaking scenery.
![Map miniature of "Montepulciano - San Quirico d'Orcia - Montepulciano" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montepulciano/road/98352.webp)
Embark on a challenging road cycling adventure to San Quirico d'Orcia, passing by iconic landmarks such as Abbadia San Salvatore and Montefollonico.
This demanding road cycling route takes you from Montepulciano to San Quirico d'Orcia and back, passing by historic towns, stunning vistas, and famous landmarks. With a high difficulty level and plenty of highlights along the way, this route is perfect for cyclists looking for an epic challenge.
Cycling routes nearby:
![Image of Montepulciano Stazione](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montepulciano-stazione-4.webp)
![Image of Torrita di Siena](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/torrita-di-siena-2.webp)
![Image of Bettolle](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/bettolle-4.webp)
![Image of Sinalunga](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/sinalunga-3.webp)
![Image of Sarteano](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/sarteano-5.webp)
![Image of San Quirico d'Orcia](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/san-quirico-d-orcia-3.webp)
![Image of Chiusi](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/chiusi-4.webp)
![Image of Foiano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/foiano-della-chiana-5.webp)
![Image of Chiusi Scalo](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/chiusi-scalo-4.webp)
Nearby regions:
![Image of Corse](https://images.tarmacs.app/cycling-routes/covers/france/corse/ghisonaccia-5.webp)
![Image of Piemonte](https://images.tarmacs.app/cycling-routes/covers/italy/piemonte/dogliani-5.webp)
![Image of Liguria](https://images.tarmacs.app/cycling-routes/covers/italy/liguria/cicagna-5.webp)
![Image of Lombardia](https://images.tarmacs.app/cycling-routes/covers/italy/lombardia/besano-3.webp)
![Image of Veneto](https://images.tarmacs.app/cycling-routes/covers/italy/veneto/camposampiero-1.webp)
![Image of Emilia-Romagna](https://images.tarmacs.app/cycling-routes/covers/italy/emilia-romagna/comacchio-5.webp)
![Image of Umbria](https://images.tarmacs.app/cycling-routes/covers/italy/umbria/castiglione-del-lago-4.webp)
![Image of Marche](https://images.tarmacs.app/cycling-routes/covers/italy/marche/santa-maria-nuova-5.webp)
![Image of Lazio](https://images.tarmacs.app/cycling-routes/covers/italy/lazio/faleria-4.webp)