Tuscany Hiking Tour From Siena Including Wine Tasting

From USD 56.84
Per Person
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Tour Information

Tour Details


Leave Siena behind and hike part of Via Francigena, an ancient pilgrimage route through rural Tuscany, followed by a wine tasting in the village of Monteriggioni. Embark on a 5-mile (8-km) trek that passes through the heart of the Tuscan countryside, past picturesque castles, villages, vineyards and ruins. Once you reach the medieval walled village of Monteriggioni, reward yourself during a wine tasting session, where you will sip on at least two organic local styles. After, head back to Siena by train at your leisure.


  • Enjoy a day away from the hustle and bustle of the city
  • Get inside tips from a local

Know More about this tour

Head to Siena train station in the morning to meet your guide, and you'll be transported by air-conditioned minivan to the starting point of the hike. Follow your guide along this picturesque and relatively easy 5-mile route, which will take you through the Tuscan countryside.

Known as the Via Francigena, this medieval route was popular in the Middle Ages for pilgrims making the journey from Canterbury in England to the Vatican in Rome. With the advent of cars and modern paved roads, Via Francigena fell from favor, but it has recently been revived and is welcoming an increasing number of hikers on its paths.

As you walk along the pretty trails, discover more about the history of the route from your guide and soak up the idyllic scenery. Pass by forest and fields, vineyards and olive groves, and look out for medieval villages and castles that look much the same as they would have centuries ago, when weary pilgrims trekked by on their way to Rome.
After around 2.5 hours of walking, arrive in Monteriggioni, an attractive walled village located in the heart of the Chianti wine region. Take part in a wine tasting in a local store, and taste at least two different local varieties.

Feel free to explore the village at your leisure, checking out the beautifully intact medieval walls and towers. Youll be provided with a map with directions to the train station (around 30 minutes away on foot) and a train ticket, which you can then use to return to Siena whenever you wish.

Inclusions for Tuscany Hiking Tour From Siena Including Wine Tasting

  • Guide
  • Transport by air-conditioned minivan
  • Wine samples
  • One-way train ticket to Siena

Exclusions for Tuscany Hiking Tour From Siena Including Wine Tasting

  • Hotel pickup and drop-off
  • Gratuities (optional)
  • Food and drinks (unless specified)

Additional Info

Confirmation will be received at time of booking, unless booked within 1 day of travel. In this case confirmation will be received as soon as possible, subject to availability

A moderate amount of walking is involved

Not recommended for people with physical disabilities or unable to walk on uneven ground and countryside footpaths for 3 hours

Comfortable shoes are recommended

Subject to favorable weather conditions. If canceled due to poor weather, you will be given the option of an alternative date or full refund

Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough passengers to meet requirements. In the event of this occurring, you will be offered an alternative or full refund

Cancellation Policy
  • If you cancel within 3 calendar days (72 hours) of the scheduled departure time, the cancellation charge will be 100% of the undiscounted tour price.
  • If you cancel between 4 to 7 Calendar days before scheduled tour departure,the cancellation charge will be 50% of the undiscounted tour price.
  • If you cancel at least 8 calendar days in advance of the scheduled departure time, there is no cancellation fee. You will receive Full Refund for the paid amount.
  • Please note that in case of No show, the cancellation charge will be 100% of the listed tour fare.
  • Please note tours booked using discount coupon codes will be non refundable.

Write A Review

9 Traveler Reviews

  • 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 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 know that you have to make your own way to the train station when it and #39;s over so be sure to ask for clear directions!

  • 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 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 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 and informative guide. The wine tasting at the end was the icing on the cake.

  • 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!

  • 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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