Cover image

Chianti Hills and Castle Tour


A road cycling route starting from Montaione

Immerse yourself in the breathtaking beauty of the Chianti region and discover ancient castles along the way.

Map

Get ready for a challenging and scenic ride through the magnificent Chianti region. This route will take you through rolling hills, charming towns, and vineyards as you explore some of Tuscany's finest landscapes. Highlights include the medieval castle of Poggio al Terraio, the historic sanctuary of San Vivaldo, and the picturesque towns of Casciana Terme, Capannoli, and Montefoscoli. As you cycle, soak up the rich history and cultural heritage of this renowned wine-growing area.

road
96 km
1257 m
Tough
Route profile

Highlights on the route

Start: Montaione Village center
Montaione: Embark on a cycling adventure in Montaione's scenic landscapes.
Montaione is a well-regarded locality for cycling in Toscana, Italy. It boasts a diverse range of routes suitable for both road cyclists and gravel riders. The hilly terrain and vineyard-dotted landscapes make for an enjoyable and scenic cycling experience. A noteworthy climb nearby is the Santo Stefano climb, known for its challenging gradients and panoramic views. With its cyclist-friendly environment and various cycling routes, Montaione is an excellent choice for cyclists of all levels looking to explore the beauty of Tuscany.
Poggio al Terraio352 mPeak
San VivaldoHamlet
San Vivaldo is a sacred hill known as the Jerusalem of Tuscany, featuring a complex of chapels that replicate the Holy Land.
Casciana TermeVillage
Casciana Terme is a peaceful town famous for its thermal baths and beautiful gardens.
CapannoliVillage
Capannoli is a delightful medieval village perched on a hill, offering panoramic views of the surrounding countryside.
MontefoscoliHamlet
MontaioneVillage
Montaione is a vibrant town with a rich history and a great place to enjoy a post-ride meal.
Finish: Montaione Village center
Montaione: Embark on a cycling adventure in Montaione's scenic landscapes.

Cycling routes nearby:

Image of Gambassi Terme
Gambassi Terme

Exploring the Scenic Beauty of Gambassi Terme on Two Wheels

Image of Castelfiorentino
Castelfiorentino

Picturesque cycling in the Tuscan countryside, Italy

Image of Certaldo
Certaldo

Enjoy scenic rides and conquer famous climbs in Certaldo.

Image of San Gimignano
San Gimignano

Italian Cycling Haven

Image of Peccioli
Peccioli

Immerse yourself in the scenic beauty of Peccioli while cycling through picturesque countryside roads.

Image of Montespertoli
Montespertoli

Experience relaxed cycling adventures in charming Montespertoli.

Image of Pozzale-Case Nuove
Pozzale-Case Nuove

Conquer the renowned climbs and embrace the beauty of Pozzale-Case Nuove.

Image of San Miniato Basso
San Miniato Basso

Scenic routes and challenging climbs in a peaceful countryside

Image of Volterra
Volterra

Cycling through the historic hilltop town of Volterra.