This moderate bike tour takes you to one of the most well-known towns in the heart of Tuscany: San Gimignano.

San Gimignano is a very popular destination for tourists (and you will see why), but fortunately, the surrounding countryside is as tranquil as any in the Chianti and we will follow some of the quietest and most panoramic roads to get there... Plus since we arrive by bike, we don't have to worry about parking!


We will begin our ride in the town of Poggibonsi. After having warmed up on a stretch of paved road, we will begin to climb on quiet, unpaved roads and trails that will carry us to our destination. Along the way, we will stop in the shade of an umbrella pine to catch our breath and enjoy the beautiful panoramas. And as we get closer to town, we will begin to understand why it is known as the "Manhattan of Tuscany," though to us it seems more like Oz.

Once we have arrived in San Gimignano, we will have plenty of time to enjoy all of its rich offerings. Strolling up via San Matteo which rises through town to the two side-by-side central squares--the Piazza Duomo and the Piazza della Cisterna--we will see and feel a fascinating blend of old and new: 17 impossibly tall medieval towers, enoteche offering wine tastings, medieval tower houses along the former pilgrammage route, boutiques selling beautifully handcrafted leather jackets and purses, narrow, winding streets, cafes, and restaurants, the Duomo, the Torre Grossa--or big tower--with its civic museum and panoramic views from the top, the best gelato you've ever had in the Piazza Cisterna, Renaissance frescoes in the Church of Saint Augustine, lunch outside at Lucia e Maria, watching passers-by, enjoying delectable sandwiches on homemade bread or a plate of homemade pasta with a glass of the local Vernaccia di San Gimignano wine. How does that sound?

After all that debauchery, we will thankfully have an easy ride back into the valley, mostly downhill and on quiet roads.

Check out our other bike tours in the Chianti area, like the Monteriggioni tour, the Greve in Chianti and Greve in Chianti 2, the San Casciano, Castellina in Chianti and Via Francigena tours.


Tour level : Moderate
Length : 17 miles (28 km)
Altitude gain : 1500 ft (500 m)
Terrain : Wide trails - dirt roads - paved roads

See Dates and Prices for more details
Contact us to reserve a tour

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