Recently Viewed
Medieval Siena: Cafes, Caves & Chianti Tasting
4.8
99 Ratings
Siena
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.
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
- Piazza San Domenico - The journey begins near the Basilica of San Domenico, where visitors can indulge in an award-winning gelato shop offering three different organic flavors.
- Via della Sapienza - Discover a hidden treasure beneath the city: a medieval cave dating back to 600 BC, not open to the public. Here, guests can immerse themselves in…
- Piazza San Domenico - The journey begins near the Basilica of San Domenico, where visitors can indulge in an award-winning gelato shop offering three different organic flavors.
- Via della Sapienza - Discover a hidden treasure beneath the city: a medieval cave dating back to 600 BC, not open to the public. Here, guests can immerse themselves in the rich history of this secret cave and admire a unique collection of red wines.
- Piazza Salimbeni - Take in the views of the world’s oldest bank, established in 1472 and still operational today.
- Piazza Tolomei - Near Piazza Tolomei, admire historical cafés, medieval buildings, hidden alleys, and neighborhoods while learning about local traditions and anecdotes.
- Piazza del Campo - Near Piazza del Campo, enjoy a distinctive wine tasting featuring local and regional sparkling wines like Prosecco, providing an educational experience.
- Via Pantaneto - Nearby, savor a delightful lunch in a typical osteria with local delicacies such as Pici pasta, pecorino cheese, cold cuts, vegetarian bruschetta with extra virgin olive oil, and Ricciarelli biscuits, all complemented by a delicious Chianti or white wine.
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
- 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
- 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…
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 Chianti & Prosecco
During this tour, enjoy sampling local food and wine such as the renowned Chianti, Pecorino cheese, bruschetta, and the homemade pasta known as pici.
Discover the myths, legends, and secrets of this medieval town while exploring iconic neighborhoods and streets where locals enjoy time with friends and family.
- Rain or shine tour will be active
- The menu may change based on the season
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.8
(99 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Chris_c
Oct 4, 2025
Our tour guide Mohad was... - Our tour guide Mohad was incredibly knowledgeable, not only about Siena’s history but also about all the food, wine and gelato places. Some of them truly hidden gems!
Perfect mix of walking tour and tasting of local specialties, all within 3 hours and away from the big tourist areas.
I would highly recommend this tour!
Review provided by Viator
Lincoln_m
Sep 30, 2025
Siena neighborhoods with food and wine - Off the beaten track….where locals find the best pasta,gelato and vino. Ancient tomb attached to an enoteca. Minimal historical information but learn about the 17 contrada and life as a resident
Guide Morad 5 STARS
Review provided by Viator
Jordyn_w
Jul 17, 2025
Great local... - Great local recommendations, very interesting information about the city, and delicious food and drinks. Morad is a great host, very friendly and knowledgeable.
Review provided by Viator
Susan_l
Jun 6, 2025
History while walking, and eating! - Amazing. Loved it. Our guide, Julie, was very knowledgeable about Siena, the rich history and the food. Can highly recommend this tour.
Review provided by Viator
Lynn_s
Jun 6, 2025
An Absolute Gem of a Tour - This was honestly one of the best tours I’ve been on, and I’ve done hundreds. Our guide was informative and interesting. We stopped for gelato tasting, wine tasting, and had a delicious lunch of traditional Tuscan cuisine. We saw so much of Siena and heard about its history. The tour with lunch was about an hour longer than what the info said so I was glad I didn’t have anything planned for afterwards.
Review provided by Viator
Joni_b
May 25, 2025
Great tour! - I recently had an amazing walking tour of Siena, and I can’t recommend it enough! Our guide was incredibly knowledgeable and truly a joy to be with, making the experience both informative and enjoyable. The city is stunning, and exploring it on foot allowed us to soak in all its beauty. Just a tip: be sure to wear comfortable shoes, as there’s plenty of walking involved. This tour is a must-do when you’re in Siena!
Review provided by Viator
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
Seema_k
Jun 13, 2025
Great lunch at the end of the tour - Julie was a wonderful guide, however I feel like there were some areas where she shared too much details that made me lose attention. Also, I felt like the description was a bit misleading, I thought this was a tour with multiple tastings and lunch at the end, but we only tasted three different gelatos in the beginning of the tour and two sparkling wines before lunch. So I suggest you have a light breakfast because the tour started at 10:30 and lunch was at 1pm.
Review provided by Viator
Quest47601388332
May 27, 2025
Julie was an excellent and knowledgeable guide. - The tour was fantastic, we saw many important areas of Siena. We learned about wine in the area, visited many historical sites and views. Most of all we had an excellent lunch and wine tasting.
Review provided by Tripadvisor
