Private Tour: Guided Hike in Tuscany with Transport from Siena

Highlights

  • 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.

Summary

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.

Tour info

Duration
7 hours
Group Size
Pricing (From)
Commentary
Meeting Point
Dropoff location

Why take this tour?

Explore Tuscany's picturesque rolling hills on a private, full-day hiking tour with transport from Siena. With your expert guide, enjoy a scenic, full-day adventurous hike through the beautiful Chianti region in Tuscany, full of forests, olive groves, vineyards and quaint villages, stopping halfway to relax over a picnic of classic Tuscan specialties. Continue in the afternoon by minivan to the medieval hill town of San Gimignano for a walk around its UNESCO World Heritage-listed city center. Spend time at your leisure browsing the main sights and boutique stores in this gorgeous town before your relaxing drive back to Siena.

What’s included?

  • Private guide

  • Round-trip transportation from Siena to Chianti

  • Transport by air-conditioned minivan (maximum 8 passengers)

  • Picnic lunch with glass of wine

  • Hotel pickup and drop-off

  • Gratuities

  • Food and drinks (unless specified)

Things to know

Before you book

  • Duration: 7h

  • Mobile tickets accepted

Covid Policy

  • Regular temperature checks for staff
  • Regularly sanitized high-traffic areas
  • Guides required to regularly wash hands

Cancellation Policy

    For a full refund, cancel at least 24 hours in advance of the start date of the experience.

Operated by:

Tuscan Escapes

About operator:

Tuscan Escapes is situated in the Siena's old center. We operate daily Tours and Activities departing from town as well as Private services throughout central Tuscany. Our aim is to guide you through this charming region and help you to experience the love of “the little things” that decorate the Tuscan way of life.

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