![Cover image](https://images.tarmacs.app/cycling-routes/photos/italy/toscana/5300948700/la-rocca-2.webp)
Monteriggioni Loop
A road cycling route starting from San Gimignano
A scenic road ride exploring the medieval towns near San Gimignano.
Map
![Map miniature of "Monteriggioni Loop" cycling inspiration in Toscana, Italy. Generated by Tarmacs.app cycling route planner](https://images.tarmacs.app/cycling-routes/routemaps/600/italy/toscana/san-gimignano/road/98482.webp)
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.
road
88 km
1395 m
Tough
Route profile
Highlights on the route
0 km
0 km
Start: San Gimignano Village centerSan Gimignano: Italian Cycling Haven
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.16 km
16 km
PoggibonsiTownExplore Poggibonsi, a historic town with a charming old town center and local markets.
17 km
17 km
Poggio Imperiale199 mPeakDon't miss the chance to visit Poggio Imperiale, a hilltop offering sweeping views of the Tuscan countryside.
29 km
29 km
MonteriggioniVillagePedal through Monteriggioni, a fortified village with well-preserved medieval walls and a charming town center.
48 km
48 km
Poggiali301 mPeakReach the summit of Poggiali and be rewarded with stunning views of the surrounding landscape.
53 km
53 km
Santa ColombaHamletPass through Santa Colomba, a picturesque hamlet known for its tranquil atmosphere and beautiful scenery.
63 km
63 km
Monte Quegna514 mPeakReach Monte Quegna and experience the serenity of this hilltop surrounded by nature.
75 km
75 km
Sant'AndreaHamletExplore the historic center of Sant'Andrea, a small town with narrow streets and traditional architecture.
87 km
87 km
ex Chiesa di San FrancescoAttraction88 km
88 km
La RoccaViewpointExplore La Rocca, a fortified fortress in San Gimignano that offers a glimpse into the town's history.
88 km
88 km
Finish: San Gimignano Village centerSan Gimignano: Italian Cycling Haven
Cycling routes from San Gimignano:
San Gimignano Road Loop Chianti Gravel Adventure Monteriggioni Loop Chianti Classic From San Gimignano to Greve in Chianti San Gimignano Scenic Route Historical Gravel Ride San Gimignano Gravel Loop Off-Road Adventure Gravel Escape Gravel Tour through San Gimignano Countryside Road Cycling Adventure around San Gimignano
Cycling routes nearby:
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![Image of Gambassi Terme](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/gambassi-terme-5.webp)
![Image of Poggibonsi](https://images.tarmacs.app/cycling-routes/covers/italy/toscana/poggibonsi-1.webp)
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