Tuscany Hiking Tour from Siena Including Wine Tasting

Siena, Italy

From $54.52

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 4 hours (approx.)
  • 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 recommended for people with physical disabilities or unable to walk on uneven ground and countryside footpaths for 3 hours
  • Comfortable shoes are recommended
  • Not wheelchair accessible
  • 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 guide was knowledgeable and fun. It was a large group and he was able to accommodate everyone. Just a really fun day!


46 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 46 reviews
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.
Beautiful hike with fantastic wine tasting!
Steve_W, Apr 2023
We had a fantastic hike with Ellena( spell?)! She was a terrific guide who told so many wonderful stories about the history of the Via Francega and Monterrey. And the wine was fantastic…. Order the cheese tasting. Best pecorino ever!
Informative, beautiful hike
Kathy_J, Apr 2023
Our guide, Kaco (sp?) was amazing!! He was very knowledgable and friendly. The hike was beautiful and the wine tasting at the end was wonderful. The wine tasting host knew his wines. You could tell that he enjoyed presenting the wines.
Great 4.7 mi hike
Carolyn_F, Apr 2023
Kiko was amazing and made this an extraordinary hike. He took the time to explain important points of history and clearly knew everything about the surrounding nature!
Beautiful country, great guide
Jane_S, Apr 2023
Our local guide was a wealth of knowledge. He geared our hike to history and nature. The wine wasn't so great, but we booked so we could hike and learn the area.
A delightful change from churches and art. A great way to deepen an understanding of this place.
Karen_D, Nov 2022
A truly delightful afternoon in the countryside. An easy 5 mile trek on the Via Francigena - the ancient pilgrimage route that actually runs from Canterbury to Rome. Our guide Keiko was enthusiastic and knowledgeable about the area and it’s history. Additionally he had been brought up to learning about the countryside’s wild plants and told us all about them. Oh…and wine tasting at the end was an added bonus.
The informative and...
Tania_W, Oct 2022
The informative and interesting insight into farmers and peoples lives of the region was fascinating. E-ko was knowledgeable of all plant and fauna. A great day out !
Two thumbs-up for this wonderful tour/activity!
Barbara_F, Oct 2022
Our guide was wonderful. He was so friendly and knowledgeable; I learned things about the region, the culture, plants and vegetation and so much more as we walked. It was a really beautiful hike and a comfortable pace. The wine tasting was also perfect after the hike. It was an all-around great experience. Thank you!
Lovely informative hike
Mallory_W, Aug 2022
Our guide was wonderful - gave us the history of the pilgrim road and told us all about the plants along the roadside
Loved it. Went with my...
Alexis_P, Aug 2022
Loved it. Went with my wife and mother-in-law. Great guide, beautiful scenery. Natural water sources along the route.
Keiko our guide, was a...
Ronald_O, Aug 2022
Keiko our guide, was a wealth of information and knowledge. His knowledge of History was profound. He also explained the local flora and fauna pointing out edible plants and their traditional uses. He also had an in-depth knowledge of the ecological issues facing the Italian forests. Very informative and thoroughly enjoyable.
Fabulous Tour
Gregory_J, Jul 2022
Friendly, knowledgeable guide who was happy to engage in conversation and was enthusiastic about Italy, the paths and places visited.
Tuscan hiking experience
Elizabeth_L, Jun 2022
Guide Kekko was great - lots of local knowledge - countryside and pilgrims walk were beautiful, and wine tasting super fun.
Great hike away from the crowds
Debbie_g, May 2022
Great local guide who was very knowledgeable on the area both history and fauna . Beautiful scenery .
We loved it
Lucera_W, Jul 2021
The whole experience was fantastic. The hike was incredible and our tour guide, Francesco, was a joy to hike with. The wine tasting was the perfect end to the journey. 10/10 recommend
Hiking for wine.
Donna R, Oct 2019
Francesco was an excellent tour guide. We enjoyed hiking five miles and learning about Tuscany’s beautiful land. Our guide was very kind and informative. We finished at the Fort of Monteriggioni for a wonderful wine tasting! I highly recommend this tour. Enjoy❤️
Pleasant walk, friendly and informative guide
IG0801, Aug 2019
A nice walk along a well marked and famous hiking path. Montereggio is a picturesque medieval village with its place in tuscan history. Sampled some great local wine and olive oil before finding a place for a traditional lunch.
via Francigena walk & wine tasting
Donald_W, Jun 2019
I would highly recommend this tour. Our guide, Keko, stopped at many points along the way to talk about the history of the path. Finishing with a wine tasting at Monteriggioni was an added plus. It is a long walk, so travel light, wear a good pair of shoes and bring liquids. There is a spot to fill your water bottles along the way. ENJOY!
Hiking Tour
jdunion, Jul 2018
Excellent Tour Guide (KeeKo) and excellent Hike!! Staff at winery were friendly and accomadating and the wine was delicious!
Our tour was fantastic. Our guide...
Treicia S, Sep 2017
Our tour was fantastic. Our guide Milos was excellent and had great knowledge of the area and its history. Would recommend.
I loved this trip! The hike from...
Macy H, Jun 2017
I loved this trip! The hike from Siena to Monteriggioni is beautiful and not too strenuous. The wine tasting was stellar, mostly because of our knowledgeable and hilarious hostess. Our hiking guide was also incredibly amiable and very knowledgeable about the history of the surrounding areas.
Your was good and worth it but just...
JA C, Jul 2016
Your was good and worth it but just know that you have to make your own way to the train station when it's over so be sure to ask for clear directions!
This can be a HOT walk in the...
Kristen L, Aug 2015
This can be a HOT walk in the summer...just FYI. But it is also totally worth all of it. Monteriggioni is beautiful, and the hike there is so pleasant. Take this tour.
This tour was really great, the...
Monty D, Aug 2015
This tour was really great, the guide was very friendly and enjoyable to walk with. The wine tasting was equally friendly, interesting and tasty. Also seemed quite generous compared to what I've heard from reviews of other tastings. Lovely village to look around too.
this is a great 1/2 day to spend in...
Julia G, Jul 2015
this is a great 1/2 day to spend in the Tuscan countryside from Siena! Our tour guide was knowledgeable and fun to walk with. Should offer more of these hikes! One point: our guide did not give us a map/directions to the train station which meant we practiced our Italian trying to find it. She did give us oral directions but it is not straightforward to get to the train station.
Great small group tour with friendly...
Judith B, Jun 2015
Great small group tour with friendly and informative guide. The wine tasting at the end was the icing on the cake.
Tuscany Hiking tour was one of the...
Hisako J, Jun 2015
Tuscany Hiking tour was one of the best tours I've ever had. Marella was very informative and also funny and thoughtful. I recommend this tour to anyone! Hisako
Fantastic day! Incredible scenery...
Amy L, May 2015
Fantastic day! Incredible scenery. Marella was an excellent guide-- knowledgeable and engaging. She was exactly the right balance of professionalism and friendliness. If you are in the area, this tour is not to be missed.

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