Grand Tour of Vernaccia di San Gimignano

A 96-mile (154-kilometer) route named after the famous wine produced in the hills of San Gimignano, declared a UNESCO World Heritage Site in 1990 due to the enchantment of its well-preserved historic center. It is well worth taking an extensive break in this town for the majesty of its towers, the beauty of its monuments and the many surprises it holds for visitors.

The route, mostly along secondary paved roads and fairly easy going, has many ups and downs which can be tackled over several days, depending on the time available.

We get on our bikes and, starting from the Piemma grove in Santa Lucia, begin the Grand Tour of Vernaccia, rewarded by unparalleled views of San Gimignano. 
Once at Colle di Val d’Elsa, the “Bohemia of Italy,” we spy the Abbey of Santa Maria Assunta in Coneo along Via Francigena. It might be worth taking a pleasant detour along this ancient pilgrimage route before heading to Casole d’Elsa, a well-preserved medieval town that holds remarkable Etruscan artifacts, as well as being a popular cycling destination thanks to the “Terre di Casole Bike Hub.”

After coming across Pievescola, we begin a beautiful and challenging climb. Some of the slopes are in double digits, but the picturesque Montagnola Senese—brimming with parish churches, castles and Etruscan necropolis—repays any effort required. The descent offers extraordinary scenic views, so much so that you might want to touch on the brakes ever so lightly to fully enjoy them.

We follow the old Strada Cassia until we spy Monteriggioni—the castle with unique walls and 14 stone towers, standing out against the panorama from atop a gentle hill. Even today, this ancient village still arouses the same fascination that enchanted Dante Alighieri in the early 1300s. The Bike Point is located at the Colonna di Monteriggioni, at the foot of the castle.
This somewhat easy ride still requires attention be paid to vehicular traffic.  Still, the encounters with art and history require much respect—from Abbadia a Isola, a pilgrim’s retreat along Via Francigena, to Colle di Val d’Elsa.

Poggibonsi, although industrially oriented, retains lofty bastions of antiquity, such as the Basilica of San Lucchese and the formidable Fortezza di Poggio Imperiale, designed by Giuliano da Sangallo.  Well worth a visit is the Archeodrome, a reconstruction of a village from the Carolingian era, where archaeologists and young people in costume partake in the daily activities of the village.  In the Fortezza and the historic town center of Poggibonsi, we encounter numerous works of contemporary art, including fine sculptures and murals.

Now, take the SP95 provincial road until turning off towards Ulignano, before turning at Sant’Andrea and entering the production area of Vernaccia, San Gimignano’s precious DOCG white wine with truly ancient origins, the first among Italian whites to have been awarded the DOCG appellation.
The SP1 provincial road winds up through vineyards and olive groves until reaching San Gimignano, where you can enjoy a well-deserved rest.

From the historic center, we set off once more to return to the Bike Point located at the Villaggio del Pellegrino—the Pilgrim Village—in the Boschetto di Piemma. The route requires some effort, particularly to reach Poggio del Cornocchio in the Castelvecchio Nature Reserve. 
The road passes through dense forests and pastures, backdropped by views of the Volterra countryside and the Colline Metallifere. As we join up with the SS68 state road, you can spot the Montemiccioli Tower then Castel San Gimignano. From here, take a detour to San Donato before returning to San Gimignano without ever losing sight of the fine vineyards producing the Vernaccia di San Gimignano grapes that are transformed into Italy’s most famous white.
The stop deserves to be long and restful. This place can only be honored, in addition to a glass of the much-loved wine, by another local excellence, the renowned Zafferano DOP. This world-class saffron can be enjoyed in traditional recipes or even gelato. A visit to the Civic Museums, rather, will delight your eyes with the wonders of medieval frescoes and historic halls.