![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/5300948700/la-rocca-2.webp)
Scenic Road Cycling through Tavarnelle Val di Pesa, Poggibonsi, and San Gimignano
A road cycling route starting from Montespertoli
Discover the beauty of the Tuscan countryside on this scenic road cycling route
Map
![Map miniature of "Scenic Road Cycling through Tavarnelle Val di Pesa, Poggibonsi, and San Gimignano" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/montespertoli/road/93009.webp)
Embark on an unforgettable cycling adventure through the enchanting Tuscan countryside, as you cycle from Montespertoli through Tavarnelle Val di Pesa, Poggibonsi, and San Gimignano. Enjoy the ever-changing scenery of rolling hills, vineyards, and cypress-lined roads. Visit charming towns along the way, delve into their rich history, and savor the authentic flavors of Tuscany. This road cycling route provides a perfect balance between challenging ascents, awe-inspiring landscapes, and cultural discoverie
road
66 km
949 m
Tough
Route profile
Highlights on the route
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Start: Montespertoli City centerMontespertoli: Experience relaxed cycling adventures in charming Montespertoli.
Montespertoli is a captivating town in the Toscana region of Italy, known for its beautiful vineyards and olive groves. From a cyclist's point of view, Montespertoli offers a mix of flat and softly rolling terrain, making it suitable for leisurely rides and beginner cyclists. The area surrounding Montespertoli is rich in natural beauty, offering cycling routes with picturesque views. One of the well-known routes nearby is the Montespertoli - San Miniato loop, which takes you through scenic countryside. Overall, Montespertoli is a great destination for relaxed cycling adventures.14 km
14 km
Tavarnelle Val di PesaVillageTavarnelle Val di Pesa is a delightful town in the heart of Chianti, surrounded by vineyards and olive groves. Explore its medieval streets, sample the local wines, and visit the olive oil mills.
26 km
26 km
PoggibonsiTownPoggibonsi is a charming town with a rich history dating back to Etruscan times. Admire its medieval towers and visit the Museum of Sacred Art to discover a treasure trove of religious artifacts.
26 km
26 km
Poggio Imperiale199 mPeakPoggio Imperiale is an imposing hill overlooking the captivating Tuscan landscape. Enjoy panoramic views as you cycle to the top and marvel at the beauty of the surrounding countryside.
37 km
37 km
San GimignanoAttractionSan Gimignano is a UNESCO World Heritage Site famous for its multiple towers that dominate the skyline. Wander through its medieval streets, taste the local gelato, and explore its rich cultural heritage.
37 km
37 km
La RoccaViewpointLa Rocca is a fortified castle perched atop a hill, offering spectacular views of the surrounding vineyards and olive groves. Take a moment to appreciate the historic significance of this impressive landmark.
49 km
49 km
CertaldoTownCertaldo is a charming medieval town with narrow, winding streets and ancient buildings. Explore its architectural gems, including the Palazzo Pretorio and the Church of Saint Michael.
56 km
56 km
Castello di OlivetoCastleCastello di Oliveto is a magnificent castle dating back to the 15th century. Admire its well-preserved architecture and learn about its fascinating history.
66 km
66 km
Castello SonninoCastleCastello Sonnino is a historic castle surrounded by beautiful gardens and vineyards. Take a tour of the wine cellars and taste the exquisite wines produced on-site.
66 km
66 km
Finish: Montespertoli City centerMontespertoli: Experience relaxed cycling adventures in charming Montespertoli.
Cycling routes from Montespertoli:
Gravel Through Montelupo Fiorentino, Campi Bisenzio, Scandicci, and La Poggiona Road Cycling in San Casciano in Val di Pesa, Chiocchio, Poggio di Rugliana, and Greve in Chianti Scenic Gravel Route The Gravel Adventure Ultimate Road Cycling Challenge via San Casciano in Val di Pesa, Greve in Chianti, and Radda in Chianti Scenic Road Cycling through Tavarnelle Val di Pesa, Poggibonsi, and San Gimignano Gravel Adventure through Bargino, Poggio Macia Morta, Castellina in Chianti, and Lucardo The Tuscan Hill Ride The Montereggi Hill Adventure The Tuscan Road Adventure Taste of Chianti Gravel Adventure
Cycling routes nearby:
![Image of San Casciano in Val di Pesa](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/san-casciano-in-val-di-pesa-5.webp)
![Image of Castelfiorentino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/castelfiorentino-4.webp)
![Image of Certaldo](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/certaldo-3.webp)
![Image of Montelupo Fiorentino](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/montelupo-fiorentino-3.webp)
![Image of Pozzale-Case Nuove](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/pozzale-case-nuove-5.webp)
![Image of Tavarnelle Val di Pesa](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/tavarnelle-val-di-pesa-5.webp)
![Image of Empoli](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/empoli-4.webp)
![Image of Tavarnuzze](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/tavarnuzze-5.webp)
![Image of Lastra a Signa](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/lastra-a-signa-3.webp)