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Tuscany Hiking Tour from Siena Including Wine Tasting provided by Tuscan Escapes - Day Tours

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Tuscany Hiking Tour from Siena Including Wine Tasting

COVID-19 update: See the added health and safety measures this experience is taking.Read more
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2 adults
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Travel safe during COVID-19
What you can expect during this experience
  • Guides required to regularly wash hands
  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Gear/equipment sanitized between use
  • Hand sanitizer available to travelers and staff
  • Regular temperature checks for staff
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Updated 06/07/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
Updated 06/07/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
Go hiking into the Tuscan countryside during a guided half-day tour including a wine tasting. Set out along Via Francigena, an ancient pilgrimage route through rural Tuscany, for a trek that passes castles, villages, olive groves, and vineyards. Sip several wines, including organic styles, during a tasting session in the medieval village of Monteriggioni. Return to Siena by train at your leisure.
  • See the natural beauty of the Tuscan countryside
  • Hike along the Via Francigena to see vineyards and olive groves
  • Sample several wines during a guided tasting in Monteriggioni
  • Free time for exploring the village of Monteriggioni is included
Important Information
Departure Point
Siena Train Station, 53100 Siena, Province of Siena, Italy
Return Details
Returns to original departure point
  • Guide
  • Transport by air-conditioned minivan
  • Wine samples
  • Hotel pickup and drop-off
  • Gratuities
  • Food and drinks (unless specified)
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Additional Info
  • Confirmation will be received at time of booking
  • 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 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
  • This tour/activity will have a maximum of 16 travelers
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveler rating
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Popular mentions
Betsy N wrote a review Jan 2020
Minneapolis, Minnesota15 contributions6 helpful votes
My husband and two adult children loved our hike last June. The guide was great and talked about the area and the history of the walking path. It took us 3.5 hours and the last hour was more challenging being hilly and rocky. The wine tasting with food pairings was a perfect
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Date of experience: June 2019
Marg K wrote a review Oct 2019
Victoria, Canada22 contributions19 helpful votes
Thank you to our guide Checco for the best walking tour we have ever taken. Your knowledge and enthusiasm for the Tuscan countryside added so much to this outing. For three hours, you not only entertained us with stories but gave us such insight into the history, traditions
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Date of experience: September 2019
Linda S wrote a review Sep 2019
9 contributions2 helpful votes
We had the joy of being in the company of a great group of likeminded fun people and a guide who was a real gem! Keko brought the Tuscan history & countryside to life for us all showing & teaching us about the way of life, herbs & flora, culture, bio diversity & organic farming.
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Date of experience: September 2019
1 Helpful vote
Kwiczka wrote a review May 2019
Krakow, Poland6 contributions
It was nice to see Tuscany from this side. For people who like active recreation and hiking this trip will be ideal. Footwear for hiking or sports shoes are mandatory. The countryside of Tuscany was beautiful. Weather was great. Our guide Kikko was very nice and open. We
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Date of experience: May 2019
Drainsontour wrote a review Nov 2018
Palmerston North, New Zealand4 contributions1 helpful vote
We really enjoyed this guided tour. It was a perfect day, we were lucky that it was a sunny day with a clear blue sky in autumn. Our guide, Fransceco, was friendly and very knowledgeable about all of the surrounding plants and trees and also talked a lot about the history of the
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About the operator

Don’t take it from us – here’s what people have to say about this operator.

By: Tuscan Escapes - Day Tours
Fantastic private walking tour of Siena with Giorgia!
We did a 3-hour private tour of Siena with Giorgia this summer with our two teenage children. It was just perfect!
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Paul D
Our guide brought history alive!
We could tell within the first minute that our guide, Georgia, was going to give us a fantastic tour of Siena and w
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Couldn't have been better!
We spent 4 days with Tuscany Escapes in September’19 and had a fabulous time. We’re ashamed it’s taken us so long t
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Rob-Bob C
Private Tour from Florence to Siena with San Gimignano
Our guide, Giada, was spectacular! On time pickup, incredibly knowledgeable on the two sites (and points between).
Read more
Amazing wine tour with Davide Dionisi
We went on a sunset Wine Tour with Davide, last minute booking but absolutely THE best tour we had in Tuscany. Davi
Read more
Tuscan Escapes Brunello Wine Tour
My wife and I had an exceptional day with Giorgia on this imersive tour. She is a very knowledgeable guide teachin
Read more
Well planned walk through Sienna.
Pleasant walk through Sienna. Our GUI was extremely knowledge and communicated well in English. I highly recommend.
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A Day Under the Tuscan Sun
Wow. What an amazing experience we had. First: Small group, which is very nice. We were lucky and had such a fun gr
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Great sites, well organized, tour guide cranky
I'm traveling with my sister, brother in law and 20 year old niece for a couple of weeks in Italy. I really wante
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Andrew R
Incredible experience we will never forget
Highly recommend this day trip to do some wine tasting, tour a few Montalcino wineries, and have the time of your l
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Amazing day
We had a wonderful time on this tour. There were just 4 of us in total which was perfect. Our tour guide/driver was
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Karen H
Spectacular walking tour MUST DO!
Our tour guide Sylvia was wonderful. Her knowledge of Sienna provided us an in depth understanding of the history u
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Janet M
A Great Day!
If you are in the area don’t miss this one. The tour operator could not have been more accommodating, even going ou
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Siena Walking Tour Viator
Marela was a great tour guide, clearly explaining the 3 centers of power in medieval Siena: Banks, Government, and
Read more
Amazing!!! 10/10
We had a fantastic trip! Our tour guide David was both exceptionally knowledgeable and also just fun. They were ver
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Key Details
  • Tuscan Escapes - Day Tours, Monteriggioni
  • Duration: 4h
  • Mobile Ticket Accepted
  • Free Cancellation up to 24 hours in advance
  • Instant Confirmation
  • Languages Offered: English, Italian
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  • Free Cancellation up to 24 hours in advance
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Frequently Asked Questions about Tuscany Hiking Tour from Siena Including Wine Tasting