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Italian Cycling Haven


Cycling routes from San Gimignano

San Gimignano, located in Toscana, Italy, is a cyclist's dream destination. With its rolling hills and picturesque landscapes, San Gimignano offers a variety of routes for road and gravel cyclists to explore. The region is known for its vineyards and olive groves, making for a beautiful backdrop during rides. Cyclists can enjoy the challenge of climbing the nearby Passo di Montecucco or take a leisurely ride through the countryside, stopping to sample local wines along the way. San Gimignano is a must-visit destination for cyclists looking for both challenging climbs and stunning scenery.

Embark on an adventurous gravel ride through the scenic Chianti region.

gravel
107 km
2885 m
Tough

Discover the charm of the Chianti region as you tackle gravel tracks and take in the breathtaking landscapes along the way. This route offers a mix of challenging climbs, beautiful vineyards, and iconic towers.


A thrilling gravel ride exploring the rural landscapes near San Gimignano.

gravel
75 km
1739 m
Tough

Embark on an off-road adventure in the picturesque countryside surrounding San Gimignano. This gravel cycling route covers a distance of 75 kilometers and includes an ascent of 1739 meters, making it ideal for those seeking a thrilling and challenging ride. Highlights of the route include San Gimignano itself, with its iconic Torre Grossa, and La Rocca, a fortified fortress. As you traverse the route, you'll encounter Poggio Martinelli, a hidden gem with stunning views, and Poggio Finto, a hill that offers a sense of tranquility. The journey continues to Poggio Scornello, where you can soak in the tranquil atmosphere of the surrounding hills, and Monte Nero, a peak with expansive views. Conclude your ride with a visit to Sensano, a charming village tucked away in the Tuscan landscape.


A scenic gravel ride exploring the countryside near San Gimignano.

gravel
47 km
805 m
Chill

Get off the beaten path and explore the rural landscapes near San Gimignano on this 47-kilometer gravel cycling route. With an ascent of 805 meters, this ride is perfect for riders looking for a moderate challenge. Highlights of the route include Il Poggetto, a hill with panoramic views, and Gambassi Terme, a spa town with thermal baths and historic charm. Pedal through scenic landscapes to reach Castelfiorentino, a medieval town with a rich cultural heritage. As you continue your journey, you'll pass by Poggio ai Cieli, a hill known for its breathtaking vistas, and La Rocca, a fortified fortress in San Gimignano. End your ride at Torre di Palazzo Pellari, where you can enjoy views of the Tuscan countryside.


Immerse yourself in history as you tackle this gravel ride around San Gimignano.

gravel
44 km
955 m
Chill

Step back in time and explore the historical wonders of the area with this gravel ride around San Gimignano. With moderate climbs and notable landmarks, this route offers a unique glimpse into the region's rich history and cultural heritage.


Experience the beauty of the Tuscan countryside on this scenic road cycling route from San Gimignano.

road
57 km
1063 m
Tough

Discover the stunning landscapes and charming villages surrounding San Gimignano on this road cycling route. With moderate climbs and picturesque panoramas, this ride showcases the best of Tuscany's natural beauty.


A scenic road ride exploring the medieval towns near San Gimignano.

road
88 km
1395 m
Tough

Experience the charm of Tuscany's medieval towns on this 88-kilometer road cycling route starting in San Gimignano. With an ascent of 1395 meters, this ride offers a moderate challenge and breathtaking views along the way. Highlights of the route include Poggibonsi, a town known for its historic center, and Monteriggioni, a fortified village with impressive defensive walls. As you pedal through the stunning countryside, you'll pass by Poggio Imperiale, a hill that offers panoramic views, and Poggiali, a peak with scenic vistas. Santa Colomba, a picturesque hamlet, and Monte Quegna, a hilltop surrounded by nature, are also worth a visit. Conclude your ride at the ex Chiesa di San Francesco, a former church with a fascinating history.


A challenging road ride with stunning views from San Gimignano to Greve in Chianti.

road
99 km
2168 m
Tough

This road cycling route starts in San Gimignano and takes you on a challenging ride through the rolling hills of Tuscany. With an ascent of 2168 meters and a distance of 99 kilometers, this ride is a test of endurance and offers breathtaking views along the way. Highlights include Torre Grossa, the tallest tower in San Gimignano, and Monte Petri, a peak with panoramic views of the surrounding countryside. As you pedal through Tavarnelle Val di Pesa and Greve in Chianti, you'll pass by vineyards and olive groves, giving you a true taste of the Italian countryside. Lamole, a charming hilltop village, and Santa Maria a Grignano, a hamlet with medieval ruins, are also worth exploring along the route.


Explore the beautiful countryside surrounding San Gimignano on this scenic road cycling loop.

road
83 km
918 m
Tough

Experience the beauty of the Tuscan countryside on this road cycling loop around San Gimignano. With moderate climbs and captivating landscapes, this route offers a memorable ride through history and nature.


Experience the picturesque countryside of San Gimignano on this gravel cycling tour

gravel
43 km
749 m
Tough

This gravel tour takes you through the stunning countryside near San Gimignano, offering beautiful views and a wide variety of terrain. The route is perfect for off-road enthusiasts and offers a moderate level of difficulty. You will ride through charming villages, vineyards, and olive groves as you soak in the Tuscan landscapes. With highlights including the scenic viewpoints of Poggibonsi, Poggio Tondo, Scarna, and a captivating vista of San Gimignano, this tour offers a truly immersive experience of the region. Explore the beauty of San Gimignano's surroundings on this exciting gravel adventure.


Embark on an epic road cycling adventure around San Gimignano, taking in the breathtaking landscapes and historic sites along the way

road
92 km
1033 m
Tough

Experience the beauty and history of San Gimignano on this road cycling adventure. The route takes you through rolling hills, charming villages, and iconic landmarks, offering a mix of challenging climbs and fast descents. With highlights including the medieval town of Monteriggioni, Poggio Imperiale, Poggiali, Poggio della Castellaccia, Casole d'Elsa, Borgatello, and La Rocca, this tour provides a truly immersive experience of the region. The difficulty level is moderate to challenging, making it suitable for well-trained amateur cyclists. Don't miss the opportunity to discover the rich cultural heritage and stunning landscapes of San Gimignano and its surroundings.


Cycling routes nearby:

Image of Certaldo
Certaldo

Enjoy scenic rides and conquer famous climbs in Certaldo.

Image of Gambassi Terme
Gambassi Terme

Exploring the Scenic Beauty of Gambassi Terme on Two Wheels

Image of Poggibonsi
Poggibonsi

Cycling paradise amidst Tuscan beauty with famous wine route nearby

Image of Colle di Val d'Elsa
Colle di Val d'Elsa

A cyclist-friendly town with a mix of flat and hilly routes.

Image of Montaione
Montaione

Embark on a cycling adventure in Montaione's scenic landscapes.

Image of Tavarnelle Val di Pesa
Tavarnelle Val di Pesa

Scenic Cycling in Tavarnelle Val di Pesa

Image of Volterra
Volterra

Cycling through the historic hilltop town of Volterra.

Image of Castelfiorentino
Castelfiorentino

Picturesque cycling in the Tuscan countryside, Italy

Nearby regions:

Image of Corse
Corse

Embark on a cycling adventure through the enchanting landscapes of Corse.

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Image of Piemonte
Piemonte

Conquering the iconic climbs and savoring the local cuisine of Piemonte.

Image of Liguria
Liguria

Conquer legendary climbs and enjoy breathtaking coastal routes in Liguria

Image of Lombardia
Lombardia

Conquering legendary climbs in Lombardia

Image of Emilia-Romagna
Emilia-Romagna

Conquer legendary climbs and savor gastronomic delights in Emilia-Romagna

Image of Umbria
Umbria

Cycling through the picturesque Umbria

Image of Marche
Marche

Enjoying the best of coastal and hillside cycling in the beautiful Marche region.

Image of Lazio
Lazio

Discover the treasures of Lazio on two wheels.