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Wine Tour: Boutique Wineries & Scenic Views
5.0
25 Ratings
Siena
Experience the best of Chianti wine, explore the underground caves of Siena, and wander through the medieval streets of San Gimignano on this semi-private tour. Limited to 6 people, enjoy personalized attention and a flexible schedule.
Experience the best of Chianti wine, explore the underground caves of Siena, and wander through the medieval streets of San Gimignano on this semi-private tour. Limited to 6 people, enjoy personalized attention and a flexible schedule.
Duration:
9 hours
Cancellation:
24 hours
Highlights
- Siena - Begin with an introduction to Siena’s rich history by a licensed tour guide, followed by a visit to a hidden underground medieval cave dating back to 600 BC.
- Castellina In Chianti - The next destination is a remarkable organic boutique winery, family-owned since 1904. Experience the charm of the Chianti region, surrounded by stunning…
- Siena - Begin with an introduction to Siena’s rich history by a licensed tour guide, followed by a visit to a hidden underground medieval cave dating back to 600 BC.
- Castellina In Chianti - The next destination is a remarkable organic boutique winery, family-owned since 1904. Experience the charm of the Chianti region, surrounded by stunning views of the Tuscan hills. Enjoy wine tasting and a tour of cellars dating back to the 1500s, along with a delightful Tuscan lunch featuring Pecorino cheese, cold cuts, and homemade pasta.
- Montalcino - Visit a family-owned boutique winery to savor Brunello di Montalcino while taking in breathtaking valley views. Explore the cellars and discover the secrets of Brunello di Montalcino wine, acclaimed as the best wine in the world in 2023.
- Val d’Orcia - Relish the beautiful rolling hills and the UNESCO site of Val d’Orcia, where scenes from the movie Gladiator were filmed.
- Pienza - The final stop is the charming town of Pienza and Val d’Orcia, offering impressive landscapes and known as the “Touchstone of Renaissance Urbanism.” Pienza is an artistic gem in the Val d’Orcia landscape, perfectly blending architectural beauty and harmony. Pienza is also famous for its Pecorino cheese.
What's Included
- Organic Balsamic vinegar & Extra virgin Olive oil tastings
- Exclusive access to a Medieval cave underground
- Tour of 2 wineries historical cellars
- Air-conditioned vehicle max 6 people
- Alcoholic beverages
- Brunello di Montalcino, Super tuscans, Chianti Classico & Rosè wines
- Licensed tour guide
- Lunch
- Organic Balsamic vinegar & Extra virgin Olive oil tastings
- Exclusive access to a Medieval cave underground
- Tour of 2 wineries historical cellars
- Air-conditioned vehicle max 6 people
- Alcoholic beverages
- Brunello di Montalcino, Super tuscans, Chianti Classico & Rosè wines
- Licensed tour guide
- Lunch
What's Not Included
- Museums tickets
- Museums tickets
Additional Information
This is a semi-private tour with a maximum of 6 participants, ensuring personalized attention. These tours offer the opportunity to fully enjoy the experience without the hassle of a crowded bus or a rigid schedule.
Participants will visit two charming, family-owned boutique wineries in a relaxed setting, providing the chance to meet the locals.
Enjoy…
This is a semi-private tour with a maximum of 6 participants, ensuring personalized attention. These tours offer the opportunity to fully enjoy the experience without the hassle of a crowded bus or a rigid schedule.
Participants will visit two charming, family-owned boutique wineries in a relaxed setting, providing the chance to meet the locals.
Enjoy tasting top-rated wines such as Chianti Classico and Brunello di Montalcino, while taking in stunning views and discovering the secrets of the world’s finest wine regions.
- This tour has been upgraded for 2025 so the reviews may be different from description.
Location
Prosperino Bistrot
Viale XXV Aprile
OUTSIDE PROSPERINO BISTROT. THE GUIDE WILL BE WAITING OUTSIDE ON THE TERRACE, NEXT TO THE OLIVE TREE STATUE.
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
5.0
(25 Ratings)
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Michelle_m
Apr 26, 2025
Amazing Experience - An absolutely perfect day! Morad was super knowledgeable and friendly and we had the best experience. Both wineries we went to were amazing as well as the other 2 stops where we got to walk around. Highly recommend this tour it exceeded my expectations!
Review provided by Viator
Elisapm9578xl
Apr 17, 2025
5 STARS - Went with my parents and we had a great time. Excellent wine, beautiful views, and a relaxed vibe. Super well organized. Highly recommend.
Review provided by Tripadvisor
Nataliaml5098ko
Apr 12, 2025
A must do experience in the heart of Tuscany - We had an amazing experience with Moro Tuscany Tours! The entire day was smooth, well-organized, and full of authentic Tuscan charm. Our driver was friendly, knowledgeable, and made us feel completely at ease. The highlight was definitely the Brunello wine tasting at a stunning winery in the hills of Siena an experience we’ll never forget! The scenery, the wine, the atmosphere just perfect.
Highly recommend this tour to anyone looking to explore Tuscany and enjoy great wine surrounded by amazing landscapes of Tuscany
Review provided by Tripadvisor
539lanep
Oct 11, 2024
Best tour experience! - If you are looking for a more intimate and educational experience this is the way to go instead of a crowded tour bus. Morad was knowledgeable about the history and local customs. The privilege of having questions answered in real time is priceless! We will definitely go back!
Review provided by Tripadvisor
Katel
Oct 13, 2023
Best tour of the Chianti region - Outstanding private tour of the Chianti region. We couldn’t have asked for a better day touring the area and tasting wines from a boutique winery. Our guide Morad was so knowledgeable and friendly and we felt the day was tailored to us. We would not hesitate to recommend this tour. Look no further!
Review provided by Tripadvisor
Susanwq434ot
Sep 30, 2023
Relaxing Toscana Tour - We really enjoy this semi private tour. It turned out to be just my husband and I and one other couple.
Sienna was beautiful, the shops seemed very good quality Italian made goods, the winery we visited had a delicious Chianti that we purchased, and San Gimignano was very interesting.
Morad, our driver was very pleasant and knowledgeable.
Would definitely recommend.
Review provided by Tripadvisor
Alan_g
Sep 18, 2023
An exceptional Tour - An exceptional tour with our exceptional guide Moro!
We contacted Moro in advance of our planned tour to customize our tour a little bit. He was accommodating and created a plan that worked perfectly. We replaced the Wine Tour part because we had this planned elsewhere. We still did the Siena Underground & San Gimignano portions. These places were absolutely wonderful. In Siena we had the best pizza & gelato during our trip. Thank you for the recommendations Moro ;) including the dinner recommendation too!
Moro was a wonderful guide and a pleasure to spend our day with. Pickup and drop off were easy as was the whole day.
I encourage you to make this a part of your plan during your stay in Florence, you'll be very happy you did.
Review provided by Viator
Sarah_m
Sep 17, 2023
Great, varied day out - Easy communication and pick up for a lovely in Tuscany. Although very busy in Siena & San Gimignano, still worth a day as beautiful. The wine tasting was very good in a beautiful winery. Moro, our guide and driver was very knowledgeable and efficient. The vehicle was not a van but a car with a small bench seat as a 3rd row. My husband in the front, 2 sisters in the middle and me in the back. It was a bit limited for leg room and a bit bumpy but I did chose to give the others more room. The drive is long, based on volume. All that said, I would recommend
Review provided by Viator
Robert_f
Aug 1, 2023
A Great Day in Tuscan Country - We signed up for this because I was trying to avoid an all-day coach bus tour but wanted to see the area and go to a winery on our family trip to Italy. Morad met us at a beautiful Piazza, and we walked a few minutes to the train station where he was parked. The car was a nice seven seat SUV which is why he limits the tour to no more than six (the sixth person will have to ride in the middle of the second seat). We were lucky to have five so everyone could easily see the pretty car ride. Morad was a great driver and we headed to Siena, his hometown. Our first stop was a wine shop, whose owner had discovered an ancient cave (Etruscan tomb?) while renovating the back of his store (thus the "underground Siena"). It was a cool experience to visit, and it is where the owner hosts wine tastings now. After that Morad hit a few highlights of the medieval city and the banking history it had also. He then gave us a few minutes free time to check out the sites and shops before we had our included lunch at a nice restaurant not for from the city center. On our way back to the car, we stopped at the wine shop for a bonus tasting and learned about Brunello wines. The shop has a popular wine club if you want to order some. From there we went to the local winery Lornano to learn about how the different wines are made and have a tasting. While there is no hard sale at the winery, when I have my wife and three daughters telling me how much they liked the wine, I did order a case. I am willing to pay a premium not to have sulphates in my wine. Our last stop was the medieval city of San Gimignano, where after waiting in line for the world champion gelato, we were limited on time to see. However, I was happy to be back to Florence by 6:00 (9 hours total). Morad is a great tour host, and the private tour was well worth every penny. Book early for this tour group because they will sell out.
Review provided by Viator
Sightsee802821
Jun 27, 2023
Fantastic Company!! - We LOVED this tour!! It is customized and easy to navigate with a small group. Many thanks to Morad for leading us on a fantastic, memorable tour. We loved the customization and pacing along with his local knowledge of the history and culture. Fantastic wine samples with incredibly friendly local people. Please book this tour! It's not your average big-bus tour where they take you to all the typical places. If you want something memorable and unique, look no further! Can't wait to go back!!
Review provided by Tripadvisor
