Medieval Siena: Cafes, Caves & Chianti Tasting

Embark on a captivating walking tour of Siena, exploring its medieval heritage and indulging in a delightful Chianti wine and food tasting experience. Discover iconic landmarks, hidden gems, and local traditions in this enchanting Tuscan city.

Duration: 2 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • Fortezza Medicea - During the tour, participants will savor organic local delicacies and wines, including the renowned Chianti wine, Pecorino cheese, bruschetta, and homemade pasta.
    Explore the myths, legends, and secrets of this medieval town. Marvel at iconic neighborhoods and historic cafes where locals enjoy time with friends and family.
    This…
What's Included
  • Vegetarian options
  • Homemade pasta, pecorino cheese, Bruschetta, ricciareli
  • Chianti wine & Prosecco
  • Small group max 12 people
  • Lunch
  • Licensed Tour Guide
  • Awarded Gelato tasting 3 flavors
What's Not Included
  • Duomo di Siena Entry Ticket €12.00
Additional Information

Join an exciting walk to explore historical cafes, local delis, medieval alleys, hidden medieval caves, and the “oldest bank in the world.”
The main highlights include:

  • A lookout offering a breathtaking view of the entire city
  • Piazza Salimbeni
  • Piazza del Campo
  • Piazza Tolomei
  • A panoramic view of the Cathedral
  • Traditional food tasting with…
Location
Hotel NH Siena
Via La Lizza
Our Meeting point will be in front of HOTEL NH SIENA (the Guide will be standing outside). We strongly suggest to type Hotel NH Siena on google maps to find us.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(91 Ratings)
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Gaildy4042vo
Apr 28, 2025
Excellent - Julie was a Great tour guide. Food and drink stops were all fun and informative. Very good and generous lunch. Highly recommend.
Review provided by Tripadvisor
Kim_s
Apr 19, 2025
Fantastic tour - Great guide friendly, knowledgeable, and fun. High quality local food homemade pasta, pecorino bruschetta, and ricciarelli. Chianti, prosecco and gelato were all top-notch. Super authentic experience!
Review provided by Viator
David_l
Oct 25, 2024
Great food, great tour - Great tour and excellent tour guide. Would absolutely recommend. The food was delicious and I learned a lot.
Review provided by Viator
Peter_b
Oct 23, 2024
Julie did a great job of entertaining us with food, stories, and wine. - Mixing history, food, and wine with a knowledgeable guide a worthwhile experience. Loved watching the horse race around the track and hearing about the tactics to win.
Review provided by Viator
William_m
Oct 5, 2024
Welcome Tour - Julie gave us an extensive historical, personal tour of Siena. A great way to familiarize us with the area, shops and sights.
Review provided by Viator
Norman_s
Sep 28, 2024
Well worth the money. - Fantastic private tour. Very informative. The guide really knows her stuff and speaks English very well.
Review provided by Viator
Lloyd_k
Sep 22, 2024
Overall great tour and insights of Siena - Julie was fantastic as a tour guide, extremely knowledgeable and very pleasant during the whole tour. As a US citizen she was also able to compare living in the US vs living in Siena, which was very interesting!
Review provided by Viator
Nicole_m
Sep 21, 2024
Good History! - Fun tour, good food and lots of history, it was a small group which made it special. Lots of walking but you don't notice how far you ha e gone and you stop at the perfect time for a snack!
Review provided by Viator
Joe_c
Oct 1, 2024
Thorough, indepth and fun tour of Siena - Our guide Julie was outgoing, lively and very knowledgeable of the city, current and historical. Mostly a walking tour with one stop for gelato and one stop for wine with meats and cheeses. We did stop at a wine store specializing in Tuscan wine and after the tour ended several us went back and had a wine tasting. If you want historical and current perspective of Siena it's a very good tour and you'll get a little bit food and wine with it.
Review provided by Viator
Jim_f
Apr 11, 2025
Missteps and a low quality lunch - Not well organized. Gelato shop nice. Sparkling wine tasting at a high quality store. Greasy pizza appetizer. Lunch a disaster! Fast food pasta shop serving overly salted pasta in cardboard takeout containers with a questionable liquid called wine to wash it down. This tour needs a total makeover.
Review provided by Viator
From $95
up to 10 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).