Ultimate Road Cycling Challenge via San Casciano in Val di Pesa, Greve in Chianti, and Radda in Chianti

A road cycling route starting from Montespertoli

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Embark on an epic road cycling journey through the iconic Chianti region

Map

Get ready for an ultimate road cycling challenge through the iconic Chianti region of Tuscany. This route takes you from Montespertoli to San Casciano in Val di Pesa, Greve in Chianti, Poggio della Cipressa, Radda in Chianti, Poggio Cavallari, Poggio Imperiale, Poggibonsi, Certaldo, and Lucardo, offering stunning panoramas, challenging climbs, and picturesque towns. Experience the thrill of cycling through vineyards, olive groves, and rolling hills while immersing yourself in the rich cultural heritage and natural beauty of Tuscany. This road cycling journey is truly an unforgettable adventure for cyclists seeking epic challenges and breathtaking experiences.

road

113 km

1914 m

Savage

Route profile

Highlights on the route

0 km

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.

17 km

San Casciano in Val di PesaTown

San Casciano in Val di Pesa is a charming town nestled in the rolling hills of Chianti. Immerse yourself in its rich history, visit the churches and palaces, and enjoy the picturesque views from its medieval walls.

35 km

Greve in ChiantiTown

Greve in Chianti is a vibrant town known for its traditional market square, lined with artisan shops and local food vendors. Treat yourself to a taste of the renowned Chianti Classico wines and indulge in the region’s gastronomic delights.

40 km

Poggio della Cipressa543 mPeak

Poggio della Cipressa is a challenging climb up a stunning hill flanked by majestic cypress trees. Ascend to the top for breathtaking panoramic views and a well-deserved sense of accomplishment.

53 km

Radda in ChiantiVillage

Radda in Chianti is a picturesque town surrounded by vineyards and olive groves. Explore its well-preserved medieval walls, visit the ancient churches, and enjoy the vibrant atmosphere of the central piazza.

64 km

Poggio Cavallari648 mPeak

Poggio Cavallari is a demanding uphill stretch that rewards cyclists with magnificent views of the Chianti countryside and the distant mountains.

82 km

Poggio Imperiale199 mPeak

Poggio Imperiale is a historic hill fort with a fascinating past. Cycle to its summit and immerse yourself in the beauty of the Tuscan landscape stretching as far as the eye can see.

83 km

PoggibonsiTown

Poggibonsi is a bustling town located on the historic Via Francigena pilgrimage route. Discover its ancient churches, visit the Fortezza Medicea, and explore the lively town center.

96 km

CertaldoTown

Certaldo is a captivating medieval town perched on a hilltop. Wander through its narrow streets, admire the well-preserved architecture, and visit the birthplace of renowned poet Giovanni Boccaccio.

106 km

LucardoHamlet

Lucardo is an enchanting village with panoramic views of the rolling Tuscan hills. Marvel at the stunning landscapes, relax in its peaceful surroundings, and recharge your energy before continuing your cycling journey.