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Drench yourself in the fabled Tuscan countryside with this private, day-long hiking tour from Siena. Meet your expert guide in Siena and then drive in a comfortable minivan to the trail where you’ll perambulate through verdant vineyards, rustic villages, and over the classic rolling hills of Tuscany. Stop halfway along the hike to indulge in a classic lunch of Tuscan treats and then travel via minivan to the town of San Gimignano, known as the ‘medieval Manhattan’ for its many gothic towers that form a medieval skyline in the 21st century. 


  • Private Tuscany hiking tour with transport from Siena
  • Hike through the vineyard-rich region of Chianti with your expert guide
  • Enjoy a picnic lunch in Chianti overlooking olive groves and vineyards
  • Explore the UNESCO World Heritage-listed town of San Gimignano at your leisure
  • Walk along the Via Francigena, an ancient pilgrimage road in San Gimignano
  • Private tour with an expert guide ensures a more personalized experience

What You Can Expect

Private Tour: Guided Hike in Tuscany with Transport from Siena

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 40-minute 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 eye-poppingly 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 ice cream (at own expense) and wandering down the winding cobblestoned 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.

Customer Reviews


5 star rating: Highly Recommended June 2016

Our private hiking tour through Chianti Classico vineyards in Tuscany was everything we hoped for and more!!
Silvia was an exceptional guide with tons of information about the area, the vineyards and the city of Siena, especially loved her recommendation for dinner!!
The hike is a bit more strenuous than we expected but Silvia was very patient and we went at a comfortable pace... The scenery was beyond spectacular and lunch was Amazing!! Especially the Chianti!!
Unfortunately we had a downpour during our time in San Gimignano but we still enjoyed the town.
Highly recommend Tuscan Escapes!!!


5 star rating: Highly Recommended June 2016

This was quite simply a wonderful day in the Tuscan countryside. We stayed in Siena for a number of nights but wanted to see the picture postcard landscape which is associated worldwide with Tuscany and we did just that. This trip gets you out among the vineyard and olive groves so you really experience the colours of Tuscany. There is really no one else about but you, your guide and every on often you come across someone working among the vines. The terracotta rooftops, the citrus trees and of course the poppies all help to leave you with images of Tuscany you will never forget. Our Guide Silivia was great and very attentive. She prepared a wonderful picnic after our walk which was a wonderful way to finish the day. Book this trip. I've read all the descriptions of the other trips on offer around the Siena area but this one is something different and does not disappoint.

Ann K

5 star rating: Highly Recommended June 2015

We had a great day with Jacopo. He tailored the hike to what we were interested in doing. Milo showed up with a great picnic lunch. Very enjoyable!


5 star rating: Highly Recommended July 2013

Milo picked us up at the arranged meeting place near the fortress in Sienna and drove us out to where we stared the beautiful walk through the vineyards. We chattered easily as we walked with Milo who enjoys good food and wine as much as we do. He was also able to give us an outline of the history of the Chainti area. Following our walk we drove to the scenic spot amongst the olive trees where Milo set up our picnic lunch. The afternoon visit to the two hilltop medieval villages gave us free time to explore and taste even more of " the worlds best gelati".

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