Tuscany Hiking Tour from Siena Including Wine Tasting

Badge of ExcellenceSiena, Italy
Tuscany Hiking Tour from Siena Including Wine Tasting
  • 4 hours
  • Mobile ticket
  • Offered in: English


Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.
  • Half-day Tuscany hiking tour from Siena including wine tasting
  • Follow part of the Via Francigena, a medieval pilgrim route that leads to Rome
  • Learn more about the history of the route from an expert guide
  • Walk between Siena and the medieval walled village of Monteriggioni
  • Soak up the stunning Tuscan scenery of rolling vine-and-olive-covered hills
  • Sip on local wine during a tutored tasting session in Monteriggioni
  • Make use the train ticket included to return to Siena

Sample Menu


3-4 different local organic wines

guided tasting of local wines that are explained by the producer

What's Included

  • Guide
  • Transport by air-conditioned minivan
  • Wine samples
  • Hotel pickup and drop-off
  • Gratuities
  • Food and drinks (unless specified)

Meeting and Pickup

Meeting point

  • Siena FS
    53100 Siena, Province of Siena, Italy

    Starting point is from outside the pharmacy next to the train stations main entrance.

Start time

09:00 AM

End point

This activity ends back at the meeting point.

What To Expect

Meet your guide at the railway station in Siena to start the tour. Hop in an air-conditioned van to the hike to the starting point. The Via Francigena is an ancient pilgrimage route, first mentioned in records in the 8th century, that stretches from Canterbury, England all the way to the Vatican in Rome, going through France and Switzerland along the way. 

While its popularity decreased with the rise of automobiles, the Via Francigena is regaining popularity as there are now regular hikers and pilgrims on the trail. Stroll along the path and notice the beauty around you: the rolling hills blanketed in olive groves and the occasional vineyard. Pass through ancient villages that look the same as they did centuries ago when pilgrims would stride past. 

After your hike, arrive at the striking village of Monteriggioni, a tiny walled town plopped atop of a medium-sized hill. Take part in a wine tasting here at a local wine shop and taste two different local varieties. After, feel free to explore the village at your leisure, popping into small shops, sitting down for lunch or investigating the medieval walls of the village. Your guide gives you a map that shows how to get to the railway station and, when you like, you can get the train back to Siena for the comfortable and scenic ride.

Additional Info

  • 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
  • Not wheelchair accessible
  • Not recommended for people with physical disabilities or unable to walk on uneven ground and countryside footpaths for 3 hours
  • Comfortable shoes are recommended
  • Service animals allowed
  • Near public transportation
  • Not recommended for pregnant travelers
  • No heart problems or other serious medical conditions
  • Travelers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 16 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • 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.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

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Featured review
Our tour guide was Amazing! He was like visiting a friend. His knowledge on the hike, people, history and the earthly and giving environment was perfect and engaging. The hike was one of the most beautiful memories I will have from my visit to Siena! This was definitely a treasure for us! I can’t say enough about the natures beauty, the historical castles and homes!


66 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 66 reviews
Unforgettable experience!
Loretta_S, Mar 2024
Our tour guide was Amazing! He was like visiting a friend. His knowledge on the hike, people, history and the earthly and giving environment was perfect and engaging. The hike was one of the most beautiful memories I will have from my visit to Siena! This was definitely a treasure for us! I can’t say enough about the natures beauty, the historical castles and homes!
Beautiful trek thru Tuscany
Beverly_S, Nov 2023
A wonderful hike to Monteriggioni with local guide Keko. It was all about the journey as Keko generously shared his extensive knowledge of flora and fauna and pointed out scenic vantage points. We had a beautiful day for the trek, and Keko was a very companionable guide.
Karla_b, Nov 2023
Sylvia was so amazing and knowledgeable! And the wine tasting was magnificent! Would recommend this adventure to everyone…
Best thing you can do in Siena!
Richard_W, Oct 2023
As if the breathtaking Tuscan countryside and Kecko’s comprehensive explanation of the history of the area wasn’t enough, Kecko also shared the history of his lifelong travels which made this hike even more personal and memorable. The wine tasting at the end was the icing on the cake, and very generous tasting portions too. 10/10 would recommend, I dare say the best thing you can do in Siena if you can just an easy 2+ hr hike!
Walking the pilgrims via francigena
John_R, Oct 2023
Lovely walk largely through forest paths. We enjoyed the company of our fellow walkers and that of Giovanni our guide. He was a delightful man with a love of nature. Monteriggioni is a small but beautiful walled village.
Wonderful hike in Tuscany
Michael_K, Oct 2023
We took a guided hike on the Via Francigena, an ancient pilgrimmage trail, which went from Siena to Monteriggioni in early September. Our guide Kecko was amazing: friendly, knowledgeable, entertaining. Not only did we learn about the history and the culture of the region, we also foraged for herbs and fruit along the trail. Our hike concluded at a winery in the beautiful walled town of Monteriggioni where we had a wonderful wine tasting. This trip was one of the true highlights of our trip to Tuscany and we would highly recommend it.
Elizabeth_M, Oct 2023
The tour was awesome! The views were breathtaking. Our guide Ricardo was very knowledgeable about the region and the history and the winemaking! We went right at the best time, because we got to see them putting the grapes right from the vineyard into the press! The tasting was great!
A break from the crowds in Siena.
Michele_R, Sep 2023
Just enough of a walk to get a feel for the countryside when you don’t have time for a heavy duty hike. Our guide Giovanni was great. He shared his knowledge and love of the landscape in English and was happy to have a chat with everyone. The wine tasting was also good. Three very good examples of local wine beautifully explained by a guy who is passionate as well as very articulate. Booking and transport ran seamlessly.
Very good
Sharon_D, Sep 2023
Guide Giovanni was wonderful!!! He was very informative and especially with regard to all the plants along the was and their traditional uses. Very nice wine sampling and food. Very enjoyable!!
Hike and wine tour.
Wailun_C, Sep 2023
Fun trip where we were picked up at the Sienna train station and shuttled to the beginning of the hike. A good part of the hike involved a part of the Canterbury to Rome pilgrimage trail. Our guide Giovanni did a great job explaining the history of the trail and of the local area. Also, we learned a lot about the local horticulture and its significance. It is not a difficult hike, but it is about 8 km or 5 miles. A bus voucher is provided for transportation back to Sienna. Wear a hat, bring water, use sun screen and at least some running or trail shoes are a must! Highly recommend.
Beautiful countryside hike!
Traci_K, Sep 2023
One of our absolute favorite tours across Italy! Great tour guide, very knowledgeable and we enjoyed meeting new friends along the way. The wine was fabulous and we were treated with food/snack pairings with each generous sample. Highly recommend!
Excellent country walk
Colin_M, Aug 2023
Excellent tour. We loved the hike which was relatively easy going on a cooler day. Beautiful countryside and knowledgeable guide - Giovanni(?) was excellent and even helped recommend other places to see in Tuscany. Wine tasting an added bonus! Recommended
A great experience!
Mona_G, Jul 2023
Keko was an awesome guide! He brought the countryside to life and taught us so much about the local vegetation and landscape. It was a hot day, but we stopped in the shade often, and there were places to refill our water bottles along the way. The views and history lessons were spectacular. Be sure to wear comfortable walking shoes! The wine tasting and food pairing in Monteriggioni felt like a well-earned treat at the end of the 6 mile hike.
A fantastic cultural experience in beautiful Tuscan setting
anneheinmaa, Jul 2023
it was not so much about hiking (only 9 km) but a cultural trip. the guide Keko was the highlight of this experience! he was so knowledgeable about local history and plants and as a person was so charming and kind. Of course Tuscan landscapes are beautiful and i enjoyed the walking part, too. I can say that that hiking trip was the best part of my 1-week vacation in Tuscany
A great hike and wine tasting!
Vineta_P, Jul 2023
A nice walk enjoying the nature of Tuscany and the guide's interesting story about the history of via Francigena, local plants and at the end of the walk the opportunity to enjoy delicious wine. Our family loved it!
Great walk along Via Francigena
Suzanne_F, Jun 2023
Walked about 8km/5m of via francigena. Beautiful scenery, was lovely to see the Tuscan countryside. Our guide was Keko, who was very knowledgeable about the area, history, route & nature. Keko pointed out different plants, herbs and insects, bought the walk alive. The wine tasting in Monteriggioni was quite brief, but a nice end to the walk. The gelato from the nearby shop was yummy. Allow at least 10 mins to get to the bus stop for the return journey Good fun, great trip. Would recommend. .
Super day!
Nadine_O, Jun 2023
Lovely walk taking time to learn about plants and nature along the way. Finishing with a nice wine tasting and well paired nibbles.
Tuscany hiking tour
ginger, May 2023
A very knowledgeable, friendly guide, well organised small group tour. The wine tasting was very good.
Our guide was...
Iris_O, May 2023
Our guide was knowledgeable and fun. It was a large group and he was able to accommodate everyone. Just a really fun day!
Carolyn_P, May 2023
After nearly two weeks in Florence and Rome among crowds of travelers, this hike was a breath of fresh air. Keko was an extraordinary guide. His passion for and knowledge of the land, his vast historical knowledge, brought the journey to life in such a meaningful way. The wine tasting was fun and inspired having quite a few bottles shipped home. We will toast Keko and the lasting memory of this unique experience.

From $59.57

up to 24 hours before the experience starts (local time)

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