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Wine Tour: Boutique Wineries & Scenic Views
5.0
28 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, presented by a licensed tour guide from a stunning panoramic viewpoint overlooking the city.
- 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 the breathtaking…
- Siena - Begin with an introduction to Siena’s rich history, presented by a licensed tour guide from a stunning panoramic viewpoint overlooking the city.
- 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 the breathtaking Tuscan hills. Enjoy wine tasting and explore cellars dating back to the 1500s, followed by 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 the stunning valley views. Explore the cellars and uncover the secrets of Brunello di Montalcino wine, acclaimed as the best wine in the world in 2023.
- Val d’Orcia - Delight in the beautiful rolling hills and the UNESCO site of Val d’Orcia, famously featured in the Gladiator movie.
- 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 celebrated as an artistic gem in the Val d’Orcia landscape, perfectly blending architectural beauty and harmony. Its most famous tradition is Pecorino cheese.
What's Included
- Organic Balsamic vinegar & Extra virgin Olive oil tastings
- Small group max 6 people
- Tour of 2 wineries historical cellars
- Licensed tour guide
- Alcoholic beverages
- Brunello di Montalcino, Super tuscans, Chianti Classico & Rosè wines
- Lunch
- Organic Balsamic vinegar & Extra virgin Olive oil tastings
- Small group max 6 people
- Tour of 2 wineries historical cellars
- Licensed tour guide
- Alcoholic beverages
- Brunello di Montalcino, Super tuscans, Chianti Classico & Rosè wines
- Lunch
What's Not Included
- Museums tickets
- Museums tickets
Additional Information
This is a semi-private tour accommodating up to six people, ensuring personalized attention. These tours offer the benefit of fully enjoying the experience without the hassle of a crowded bus or a rigid schedule.
Participants will visit two charming, family-owned boutique wineries, providing a relaxed atmosphere and the opportunity to meet local…
This is a semi-private tour accommodating up to six people, ensuring personalized attention. These tours offer the benefit of fully enjoying the experience without the hassle of a crowded bus or a rigid schedule.
Participants will visit two charming, family-owned boutique wineries, providing a relaxed atmosphere and the opportunity to meet local residents.
Guests will savor highly-rated wines such as Chianti Classico and Brunello di Montalcino, all 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
(28 Ratings)
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Rachaelto6198lz
Mar 10, 2026
Absolute GEM of a day in Tuscany!! - We had an absolutely incredible time on our tour with Morad!! We got to see his olive oil farm which was a truly unique experience. We visited Lornano and Innocenti Montalcino vineyards and had a wonderful tasting and lunch with some outstanding wines. Our day wrapped up in Pienza, which ended up being an absolute gem. Our day with Morad was my favorite of all our days in Tuscany. We can’t say enough wonderful things about this trip- just book it!! You won’t regret it.
Review provided by Tripadvisor
L3136bbmattt
Mar 10, 2026
Unforgettable Experience From The Start - Morad is the real deal. He didn’t just host us; he gave us a masterclass in local living. From the moment he picked us up, he went above and beyond—taking us through his personal olive gardens and vineyards for a truly intimate look at the land. His local knowledge is unmatched, and every detail was handled with genuine care. For the price, the value is unbeatable. Stop scrolling and book him—it’s an unforgettable experience you’ll be talking about for years.
Review provided by Tripadvisor
Joann_r
Sep 27, 2025
Wonderful Tour - Our tour guide was Marado and he was wonderful. He pointed out interesting things along the way, also showed us wonderful spots for scenic pictures.
Review provided by Viator
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
