• Location: Siena, Italy
  • Duration: 4 hours (approx.)
From USD $ 53.50 View price calendar

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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, about 5 miles (8 km), takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the village of Monteriggioni, one of the most gorgeous hill towns you’ll ever step foot in, you’ll be rewarded with a wine tasting. At the end, head back to Siena via train.


  • 4-hour 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

What You Can Expect

Tuscany Hiking Tour from Siena Including Wine Tasting

Savor local wine after your hike on this tour

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 in 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 about 2.5 hours of hiking, 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 will give you a map that shows how to get to the railway station (a 30-minute walk) and, when you like, you can get the train back to Siena for the comfortable and scenic ride.

Customer Reviews

Treicia S

5 star rating: Highly Recommended September 2017

Our tour was fantastic. Our guide Milos was excellent and had great knowledge of the area and its history. Would recommend.

Macy H

5 star rating: Highly Recommended June 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.

Julia G United States of ... 

5 star rating: Highly Recommended July 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.

Judith B

5 star rating: Highly Recommended June 2015

Great small group tour with friendly and informative guide. The wine tasting at the end was the icing on the cake.

Hisako J

5 star rating: Highly Recommended June 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!

Kristen L

4 star rating: Recommended August 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.

Monty D

4 star rating: Recommended August 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.


3 star rating: Worth doing July 2016

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!

Amy L

3 star rating: Worth doing 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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