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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.

Embark on a challenging road cycling adventure to Cortona.

road
92 km
1061 m
Tough

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.


Discover the quaint villages and beautiful countryside around Montepulciano on this gravel route.

gravel
45 km
881 m
Tough

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.


Experience the beauty of Tuscany on this challenging road cycling route starting in Montepulciano.

road
131 km
1728 m
Tough

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.


Embark on a moderate gravel cycling route from Montepulciano to Sant'Albino, passing by beautiful spots like Castiglioncello del Trinoro and Sarteano.

gravel
51 km
1393 m
Chill

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.


Embark on a gravel cycling adventure to Poggio Bianco, enjoying picturesque landscapes and sights like Petroio and Rigomagno along the way.

gravel
65 km
1323 m
Tough

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.


Embark on a challenging cycling adventure to Montalcino and Sant'Angelo Scalo.

road
140 km
2692 m
Savage

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.


Embark on a short, yet adventurous gravel cycling journey to Poggio della Cava.

gravel
33 km
885 m
Chill

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.


Explore the charming towns of Monticchiello, San Quirico d'Orcia, and Montisi on this road cycling route.

road
72 km
1264 m
Tough

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.


Embark on a scenic road cycling adventure to Chianciano Terme.

road
75 km
1077 m
Tough

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.


Embark on a challenging road cycling adventure to San Quirico d'Orcia, passing by iconic landmarks such as Abbadia San Salvatore and Montefollonico.

road
118 km
2626 m
Savage

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
Montepulciano Stazione

A charming locality in Toscana region with beautiful landscapes and nearby possibilities for famous climbs.

Image of Torrita di Siena
Torrita di Siena

Conquering the legendary Monte Amiata and immersed in stunning Tuscan landscapes.

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Bettolle

Cycling Paradise in Toscana

Image of Sinalunga
Sinalunga

Cycling Paradise in Tuscany

Image of Sarteano
Sarteano

Scenic town with access to the famous Montepulciano climb.

Image of San Quirico d'Orcia
San Quirico d'Orcia

Embark on a cycling journey through the captivating Val d'Orcia from San Quirico d'Orcia.

Image of Chiusi
Chiusi

Experience the rich history of Chiusi while cycling through its picturesque surroundings.

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Foiano della Chiana

Authentic Tuscan cycling through tranquil countryside.

Image of Chiusi Scalo
Chiusi Scalo

Relaxed rides in scenic Chiusi Scalo, Toscana

Nearby regions:

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Corse

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Piemonte

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Liguria

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Lombardia

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Veneto

Experiencing the ultimate road and gravel cycling in Veneto

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Emilia-Romagna

Conquer legendary climbs and savor gastronomic delights in Emilia-Romagna

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Umbria

Cycling through the picturesque Umbria

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Marche

Enjoying the best of coastal and hillside cycling in the beautiful Marche region.

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Lazio

Discover the treasures of Lazio on two wheels.