![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/7596274280/pienza-3.webp)
Montepulciano - Castiglione d'Orcia - Montepulciano
A gravel cycling route starting from Montepulciano
Embark on a challenging gravel cycling journey to Castiglione d'Orcia, passing by stunning landmarks like Pienza and Poggio Tullio.
Map
![Map miniature of "Montepulciano - Castiglione 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/gravel/98331.webp)
This demanding gravel cycling route takes you from Montepulciano to Castiglione d'Orcia and back, passing by iconic landmarks, picturesque landscapes, and scenic viewpoints. With a high difficulty level and a range of highlights along the way, this route is perfect for experienced gravel cyclists seeking an epic adventure.
gravel
63 km
1517 m
Tough
Route profile
Highlights on the route
0 km
0 km
Start: Montepulciano City centerMontepulciano: A famous town with challenging climbs and rolling hills.
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.1 km
1 km
Bivio San BiagioSub-urbPass by Bivio San Biagio, a small intersection with limited attractions.
10 km
10 km
Veduta delle Biancane e dei cipressi di Lucciola BellaViewpointEnjoy panoramic views of the Biancane geothermal area and the cypress trees of Lucciola Bella.
25 km
25 km
Poggio Bicchieri651 mPeakTake in the breathtaking views from Poggio Bicchieri, one of the highest points along the route.
35 km
35 km
Il Poggio424 mPeakExperience the beauty of Il Poggio, a peaceful spot with panoramic views of the surrounding countryside.
40 km
40 km
Castiglione d'OrciaVillageExplore Castiglione d'Orcia and discover its medieval castle, charming streets, and beautiful views of Val d'Orcia.
50 km
50 km
PienzaVillageVisit Pienza, a UNESCO World Heritage Site known for its Renaissance architecture and delicious pecorino cheese.
57 km
57 km
Poggio Tullio541 mPeakPass by Poggio Tullio and enjoy the scenic beauty of this hilly area with winding gravel roads and expansive views.
62 km
62 km
Fortezza MediceaCastleExplore the imposing Fortezza Medicea in Pienza, an architectural masterpiece built by the Medici family.
63 km
63 km
Finish: Montepulciano City centerMontepulciano: A famous town with challenging climbs and rolling hills.
Cycling routes from Montepulciano:
Montepulciano - Poggio Bianco - Montepulciano Montepulciano - Castiglione d'Orcia - Montepulciano Scenic Road Cycling Route to Chianciano Terme Short Gravel Adventure to Poggio della Cava Gravel Loop Montepulciano and Surroundings Montepulciano - Sant'Albino - Montepulciano Cycling Adventure to Montalcino and Sant'Angelo Scalo Montepulciano - Pienza - Montepulciano Montepulciano - San Quirico d'Orcia - Montepulciano Challenging Road Cycling Loop to Cortona Montepulciano Round-Trip Cycling
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)