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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

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

Start: Montespertoli City center
Montespertoli: 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.
Tavarnelle Val di PesaVillage
Tavarnelle 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.
PoggibonsiTown
Poggibonsi 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.
Poggio Imperiale199 mPeak
Poggio 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.
San GimignanoAttraction
San 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.
La RoccaViewpoint
La 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.
CertaldoTown
Certaldo 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.
Castello di OlivetoCastle
Castello di Oliveto is a magnificent castle dating back to the 15th century. Admire its well-preserved architecture and learn about its fascinating history.
Castello SonninoCastle
Castello 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.
Finish: Montespertoli City center
Montespertoli: Experience relaxed cycling adventures in charming Montespertoli.

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