Private Tour: Guided Hike in Tuscany with Transport from Siena

See more of Tuscany on this exciting, action-packed day-long private hiking tour from Siena. After meeting your knowledgeable local guide in Siena, hop in a comfortable minivan for the drive to the trail’s starting point. Along the way, gawk at the legendary Tuscan landscape and learn about the history of the area from your guide. 

At the trail, stroll along with your guide as you learn about the natural and historical facts of the area. Walk through olive groves, around vineyard-clad hills, and through bucolic ancient villages that look like they haven’t changed for centuries. 

About halfway through the hike, stop for a picnic lunch. Feast on prosciutto, fresh veggies, cheese, and bread. Have a glass of local wine and take in the scenery. 

After the picnic and a brief walk, meet the minivan again and hop in: head to the gorgeous medieval town of San Gimignano. Sitting atop a high hill, the town boasts several towers from the Middle Ages. Walk the streets of the town, perhaps stopping for some of its famed saffron gelato (at own expense) and wandering down the winding cobblestone alleyways 

Take another brief stroll down the Via Francigena, a medieval pilgrimage route that stretched from Canterbury in England all the way to Rome. In recent years, the route has seen a resurgence in popularity so keep your eyes out for pilgrims who are making the long walk. 

After learning about the history of the pilgrimage route, take some free time to explore more of San Gimignano, popping into the boutiques or sitting down for a glass of wine, before eventually getting aboard the minivan for the short ride back to Siena. 

Note: This hiking tour is suitable for those in good physical condition, and who have experience with relatively long walks. While the Chianti walking trails are open to everyone, it’s good to keep in mind that the area is natural and unspoiled, so the ground can be uneven and, in some places, steep and narrow.