![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/617537310/rapolano-terme-1.webp)
The Tuscan Hill Challenge
A road cycling route starting from Sinalunga
Take on the ultimate Tuscan hill challenge on this epic road route starting near Sinalunga.
Map
![Map miniature of "The Tuscan Hill Challenge" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/sinalunga/road/98470.webp)
This challenging road route near Sinalunga is perfect for experienced cyclists looking for an epic hill-climbing challenge. With a demanding ascent of 1527 meters and a distance of 117km, this ride offers a true test of endurance and strength. Highlights include the scenic I Cipressi di Baccoleno, the charming Poggio della Sorbitella, and the famous Torre del Mangia. With its mix of challenging climbs and stunning panoramas, this route provides an unforgettable cycling experience for those seeking a true Tuscan adventure.
road
117 km
1527 m
Savage
Route profile
Highlights on the route
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Start: Sinalunga City centerSinalunga: Cycling Paradise in Tuscany
Sinalunga, located in Toscana, Italy, offers a diverse range of cycling routes suitable for both road and gravel cyclists. The town is surrounded by stunning countryside and is known for its rolling hills and winding roads. Cyclists can explore the nearby Val d'Orcia, a UNESCO World Heritage Site, which offers breathtaking views and challenging climbs. Sinalunga also serves as a great base for exploring the surrounding Tuscany region and its famous cycling spots such as Montalcino and Montepulciano. With its beautiful landscapes and rich cultural heritage, Sinalunga attracts cyclists from all over the world.0 km
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SinalungaTownSinalunga - Start your ride in the charming town of Sinalunga with its medieval architecture and historic charm.
16 km
16 km
I Cipressi di BaccolenoViewpointI Cipressi di Baccoleno - Experience the breathtaking beauty of I Cipressi di Baccoleno, a scenic area filled with cypress trees and rolling hills.
31 km
31 km
BuonconventoVillageBuonconvento - Explore the picturesque town of Buonconvento, known for its historic buildings and inviting cafes.
37 km
37 km
Poggio della Sorbitella221 mPeakPoggio della Sorbitella - Conquer the challenging Poggio della Sorbitella climb, known for its steep gradients and stunning views of the surrounding valleys.
48 km
48 km
RadiHamletRadi - Discover the charm of Radi, a quiet village nestled in the Tuscan countryside with breathtaking panoramic views.
50 km
50 km
Poggio Bosco Tondo243 mPeakPoggio Bosco Tondo - Enjoy the rolling hills and scenic vistas of Poggio Bosco Tondo, a challenging climb with rewarding scenery.
57 km
57 km
Poggio ai Frati230 mPeakPoggio ai Frati - Take on the demanding Poggio ai Frati climb, known for its challenging gradients and stunning panoramic views.
68 km
68 km
Torre del MangiaAttractionTorre del Mangia - Visit the famous Torre del Mangia, a medieval tower offering panoramic views of Siena and the surrounding countryside.
75 km
75 km
ArbiaVillageArbia - Explore the quaint town of Arbia, known for its historic buildings and charming streets lined with local shops and cafes.
79 km
79 km
Colle di Monteaperti242 mPeakColle di Monteaperti - Experience the beauty of Colle di Monteaperti, a scenic area with panoramic views of the Tuscan countryside.
98 km
98 km
Rapolano TermeVillageRapolano Terme - Take a break at Rapolano Terme, a charming town known for its natural hot springs and relaxing spa resorts.
106 km
106 km
Poggio Bianco371 mPeakPoggio Bianco - Enjoy the scenic views from the top of Poggio Bianco, a challenging climb with rewarding scenery.
109 km
109 km
RigomagnoVillageRigomagno - Cycle through the charming village of Rigomagno, known for its historic buildings and inviting cafes.
117 km
117 km
Palazzo PretorioCastlePalazzo Pretorio - Visit the historic Palazzo Pretorio, an ancient palace filled with Renaissance art and stunning architectural features.
117 km
117 km
Finish: Sinalunga City centerSinalunga: Cycling Paradise in Tuscany
Cycling routes from Sinalunga:
Gravel Escape - Rolling Hills and Historic Sites The Tuscan Countryside Gravel Route - Castles and Countryside Tuscan Hills and Villages Gravel Explorations - Hilltops and Tuscan Delights Sinalunga Road Cycling Tour The Tuscan Hill Challenge Gravel Adventure - Valleys and Villages The Gravel Adventure The Ultimate Tuscan Road Ride Marciano della Chiana - Castiglion Fiorentino - Belvedere Rossano Naldi - Camucia - L'Amorosa
Cycling routes nearby:
![Image of Bettolle](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/bettolle-4.webp)
![Image of Torrita di Siena](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/torrita-di-siena-2.webp)
![Image of Lucignano](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/lucignano-3.webp)
![Image of Foiano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/foiano-della-chiana-5.webp)
![Image of Marciano della Chiana](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/marciano-della-chiana-5.webp)
![Image of Montepulciano Stazione](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montepulciano-stazione-4.webp)
![Image of Monte San Savino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/monte-san-savino-5.webp)
![Image of Montepulciano](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montepulciano-5.webp)
![Image of Rapolano Terme](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/rapolano-terme-5.webp)