Explore our promoted experiences
- 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
Departure & Return
From under the large tree next the church entrance
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What To Expect
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.
- Confirmation will be received at time of booking, unless booked within 16 hours of travel. In this case confirmation will be received as soon as possible, subject to availability
- Suitable walking shoes required (walking/hiking boots, sneakers, closed toe shoes with non-slip soles, etc.; no flip-flops)
- Due to uneven surfaces, this tour is not recommended for those with walking difficulties, those below average fitness, young children or those using a wheelchair
- Not wheelchair accessible
- No heart problems or other serious medical conditions
- Travelers should have a moderate physical fitness level
- This is a private tour/activity. Only your group will participate
- OPERATED BY Tuscan Escapes by Papilio SRL
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- Cut-off times are based on the experience’s local time.
Learn more about cancellations.
- Face masks required for travelers in public areas
- Face masks required for guides in public areas
- Face masks provided for travelers
- Hand sanitizer available to travelers and staff
- Regularly sanitized high-traffic areas
- Gear/equipment sanitized between use
- Transportation vehicles regularly sanitized
- Social distancing enforced throughout experience
- Guides required to regularly wash hands
- Regular temperature checks for staff
- Paid stay-at-home policy for staff with symptoms