Explore the Most Authentic Side of Tuscany by Bike
Experience an unforgettable cycling adventure in Tuscany with our bike tour on the Montagnola Senese, a captivating itinerary that starts in the historic city of Siena and winds through rolling hills, medieval villages, and ancient forests. Ideal for gravel and mountain bike enthusiasts, this route takes you along dirt roads and historic paths immersed in nature and history.
Cycle Touring Itinerary
Total length: approx. 50 km
Elevation gain: approx. 800 m
Route type: loop, mixed asphalt and dirt roads
Difficulty: medium (for moderately trained cyclists; e-bikes recommended for beginners)
Starting point: Siena
The tour begins at Porta San Marco, one of the ancient gates into the medieval city of Siena. After just a few kilometers, you’ll leave city traffic behind and ride westward on quiet backroads, gradually immersing yourself in the serene landscape of the Sienese countryside.
The Hills of Montagnola Senese
The Montagnola Senese is a hilly area that reaches its peak at Monte Maggio (671 m). It’s a landscape of holm oak and chestnut woods, cultivated clearings, and striking limestone rock formations. Much of the route runs along scenic white roads in the silence of nature.
Landscapes and Nature
The environment is typically wooded and wild—perfect for gravel riders and nature lovers.
You’ll ride ancient cart tracks, forest trails, and stretches of medieval roads like the historic Via Francigena.
Historical Sites and Landmarks
1. Hermitage of Lecceto
Located about 10 km from Siena, this mystical hermitage is surrounded by woods and was an important Augustinian center in the Middle Ages. It’s a peaceful, spiritual spot—perfect for a short break.
2. Castle of Celsa (view from outside only)
Riding along the white road toward Ancaiano, you’ll glimpse the elegant Castle of Celsa, a Renaissance residence with beautiful Italian gardens.
3. Villa Cetinale
A baroque gem of the Montagnola, Villa Cetinale boasts monumental gardens designed by renowned architect Carlo Fontana. Usually visible only from the outside (except on special openings), it’s an enchanting sight.
4. Parish Church of San Giovanni Battista in Molli
Dating back to the 12th century, this Romanesque church is a beautiful example of medieval religious architecture. Its stone façade and simple yet spiritual interior tell centuries of Tuscan history. Located in a panoramic forest setting, it’s perfect for a photo stop.
Fun and Technical Sections
Between Toiano and Ancaiano, the climb gets steeper, with gradients over 10%, but the road surface remains generally good.
From San Giovanni a Cerreto, enjoy a beautiful downhill stretch on a dirt path through the forest, with open views of the Elsa Valley.
Recommended Food Stops
Restaurant in Sovicille or Rosia: local cuisine and e-bike charging available.
Alternatively, enjoy a picnic in one of the many scenic spots along the route.
Return to Siena
The return to Siena goes through Sovicille and Costalpino, with one final scenic climb that brings you back to the city, offering a spectacular view of Siena and its towers.
Useful Tips
Best time to go: Spring and early autumn
Recommended bike: gravel or mountain bike; an e-bike is helpful on the climbs
Gear: bring water, a repair kit, and lights if departing in the afternoon
Navigation: GPX map recommended for off-road sections (contact us for the track)
Book Your Bike Tour from Siena Now
Let yourself be surprised by the Montagnola Senese by bike, a hidden corner of Tuscany waiting to be discovered—full of unspoiled nature and timeless villages. Book your tour today and experience the cycling adventure you’ve been dreaming of.
Why Choose This Bike Tour?
Exclusive route away from mass tourism Immersive experience in Tuscan nature and history Safe, scenic paths—perfect for unforgettable photos Customizable options for private groups or families
Pedaliamo’s Tip
Want to explore Tuscany on two wheels, stress-free?
We organize customized bike tours including:
Bike rental (gravel, trekking, e-bike)
Expert local guide and assistance on route
Tastings or light lunches in selected locations
Typical accommodations in charming lodgings
Luggage transport and transfers
Whether you’re a solo traveler, a couple, or a group of friends, we can create a tailored experience to help you enjoy Tuscany in an authentic, active, and relaxed way. Whether for a day trip or a slow weekend getaway—we’re here to guide you every step of the way, pedal by pedal.
Contact us for the full program or a personalized proposal!
Your adventure starts here. 
