Tours and Tickets
Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA
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Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

By We Drive You Tuscany
Recommended by 100% of travelers
100% of reviewers gave this product a bubble rating of 4 or higher.
About
from
$486.28
per adult (price varies by group size)
Lowest price guarantee

Ages 21-99
Duration: 8h
Start time: Check availability
Mobile ticket
Live guide: Portuguese, English, Italian, French
More


  • WiFi on board
  • Private transportation
  • Door-to-door pick-up and drop-off
  • Air-conditioned vehicle
  • Bottled water
  • Entry/Admission - Azienda Agricola Capanna di Cencioni
What's not included
  • Eventual entrance fees
  • Lunch
  • Gratuities
  • Wine tasting fees


Start:Multiple pickup locations offered.
    Pickup details
    • We are available for collecting you everywhere in town and surroundings
    Hotel pickup offered
    During checkout you will be able to select from the list of included hotels.
      Airport pickup offered
      During checkout you will be able to select from the list of included airports.
      • Aeroporto di Siena, Str. dell'Aeroporto, snc, 53018 Ampugnano SI, Italy
      End:This activity ends back at the meeting point.

        • Not wheelchair accessible
        • Near public transportation
        • Infants must sit on laps
        • Infant seats available
        If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 21405P8

        • Vegetarian option is available, please advise at time of booking if required
        • A minimum of 2 people per booking is required
        • A maximum of 8 people per booking
        • Operates in all weather conditions, please dress appropriately
        • Travelers should have a moderate physical fitness level
        • This is a private tour/activity. Only your group will participate

        • All sales are final and incur 100% cancellation penalties.

        Which attractions will I visit with Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA?
        How much is Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA?
        Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA price starts from $484.69. Discover and book Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA on Tripadvisor
        What is the Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA cancellation policy?
        Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA cancellation policy: All sales are final and incur 100% cancellation penalties. Discover and book Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA on Tripadvisor
        Which company provides Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA?
        Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA is hosted by We Drive You Tuscany. Read reviews, discover additonal experiences or contact We Drive You Tuscany on Tripadvisor. Discover and book Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA on Tripadvisor

        If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 21405P8

        Reserve your spot
        Itinerary
        • You'll get picked up
          See departure details
        • 1
          Azienda Agricola Capanna di Cencioni
          Stop: 90 minutes - Admission included
          See details
          Pass by
          Montalcino
        • 2
          Pienza
          Stop: 30 minutes
          See details
          Pass by
          Val d'Orcia
        • You'll return to the starting point
        About the operator
        Don’t take it from us – here’s what people have to say about this operator:
        • We Drive You Tuscany
          172
          Siena, Tuscany, Italy
          Joined in February 2011
        • OnAir788845
          0 contributions
          2.0 of 5 bubbles
          Bait and Switch
          Over promise, under deliver! They seemed really professional and great when I was in the booking phase and when I mentioned that I was a wine professional they told me that they had a qualified "sommelier" who would be my driver. They even confirmed this the afternoon before my trip. the morning of my trip I got a crabby driver who clearly didn't want to be there and was not a sommelier. I would never have paid that price if I had known what I was getting. Thoroughly disappointed. It was so-so but I feel they weren't upfront and overpromised.
          Written October 21, 2023
        • ardentempest
          0 contributions
          5.0 of 5 bubbles
          Recommend to everyone wanting an amazing authentic experience
          We had an EXTRAORDINARY time with Emanuale. He was punctual, professional, incredibly helpful and very knowledgeable about the history of the area as well as the wine of the region. He had great recommendations, provided us with opportunities to see the most amazing views and really gave us an appreciation of your beautiful Tuscany. He is a true gem and asset to your company!! When we come back I sure hope he is still available!
          Written October 11, 2023
        • ellasf
          0 contributions
          5.0 of 5 bubbles
          Excellent Tuscan experience
          Maurizio was friendly, knowledgeable, professional and a great driver. What a perfect day through Tuscany! Highly recommend.
          Written October 8, 2023
        • reneemJ5630MQ
          0 contributions
          5.0 of 5 bubbles
          Highly Recommend
          The owner worked with us (and truly saved us!) with a last minute need for a driver for dinners as well as a few day tours. We had an EXTRAORDINARY time with Emanuele, our guide . He was punctual, professional, incredibly helpful and very knowledgeable about the history of the area as well as the wine of the region. He had great recommendations, provided us with opportunities to see the most amazing views and really gave us an appreciation of your beautiful Tuscany. The owner made it easy for us to pay, easy to schedule. We could not have been happier with our service. When we come back we will certainly be using them again!
          Written October 5, 2023
        • demid807
          0 contributions
          5.0 of 5 bubbles
          Brunello Wine Tasting
          Roberto was incredible and so knowledgeable on a variety of topics. He was funny and kept the conversation lively. He truly loves what he does and it does not go unnoticed. The wineries we went to were small production and you can tell how much passion they have for wine making. They made us feel like they were part of our family. The lunch we had was incredible and homemade. Roberto picked us up directly at our accommodation and dropped us off. I highly recommend booking with this group as they truly care about your experience in Italy. Grazie mille for a lovely experience
          Written October 4, 2023
        • Departure68179384817
          0 contributions
          5.0 of 5 bubbles
          Chianti Classico/Montepulciano/Cortona Tour - PERFECT
          With Roberto as our driver and guide over two days, we had an amazing experience! We Drive You customized two days of wine tastings at 8 boutique wineries to give us a range of experiences, and it did not disappoint. Roberto was knowledgeable, friendly, and easy to get along with. He gave us unique perspectives which really helped us compare the different areas we toured. The wineries themselves were also incredible! It seems We Drive You has gone to great lengths to cultivate excellent relationships with the boutique wineries, and it really shows. My wife and I had never visited Tuscany, and now I can't imagine doing it any other way. Thank you Roberto and We Drive You!
          Written September 21, 2023
        • Curious778051
          0 contributions
          5.0 of 5 bubbles
          Maurizo best driver in Siena and Italy
          Maurizio was our best driver in Italy The quote I think is :meet as clients leave as friends. Maurizio met us off plane in Rome and we had a private tour to Siena with stop on way at Montepulciano 2 days later we hired for half a day.brilliant.
          Written September 2, 2023
        • Y2146QFjl
          0 contributions
          5.0 of 5 bubbles
          Chinati and area tour
          Fantastic week with Roberto who saved the day after an issue with our hire car. Knowledgable, fun and flexible. A Gentleman!
          Written August 24, 2023
        • 5ExpatsInAsia
          0 contributions
          5.0 of 5 bubbles
          Great experience
          We were just looking for a transfer from Siena to the Pisa airport. Wanted a driver who would take us to the Leaning Tower and stay with our car/bags on the way. So we hired them for that. Roberto was our driver and he was great. We didn't expect a tour or historical facts, but he had them! His English was great, too. Safe and smooth driver. Everything went smoothly and I would totally request him again if we were to go back.
          Written July 3, 2023
        • Nomad750051
          0 contributions
          5.0 of 5 bubbles
          Very unique local experience that takes you off the typical tourist track
          What an amazing tour! Emanuele picked us up in a nice spacious Mercedes van at our hotel in Tuscany and took us to great places that are off of the beaten track of most tourists. One such place was the private home of local farmer and chef Alessandro, where he prepared a spectacular lunch made from food he has raised and grown. His olive oil, his salami, his balsamic vinegar aged more than 20 years. The view from his Villa was stunning. I highly recommend this unique experience.
          Written June 22, 2023
        • T763TTpattim
          0 contributions
          5.0 of 5 bubbles
          Highly recommend
          Totally worth it! We had the best service and it added to our trip. Highly recommend! So much better than trains.
          Written June 11, 2023
        • shannonv894
          0 contributions
          5.0 of 5 bubbles
          We Drive You is the best!
          Our group o 16 used We Drive You Tuscany throughout our week. We used them for both transfers and planned tours. Tours: Brunello wine tour and the Val d'Orcia Chianti Classico and San Gimignano Both tours were amazing, once in a lifetime experiences. The wineries selected were boutique and so beautiful. Wine was delicious. The lunches planned were phenomenal. We started planning this trip over a year ago and Tomas, Roberto and Michela were wonderful, detailed and responsive. The drivers were wonderful and always on time and shared great history and knowledge. HIGHLY RECCOMEND
          Written May 23, 2023
        • Q451ATcynthiag
          0 contributions
          5.0 of 5 bubbles
          Fantastic Tuscan wine tour
          Maurizio was a fantastic guide and driver. He had a wealth of knowledge for Tuscany and the stops on the tour. The lunch at the boutique winery, Azienda Agricola Rocca, in Chianti was like a dream or a movie. Eating lunch amongst the olive trees and eating the homemade food was a highlight of our trip. The second winery, I Fabbri di Susanna Grassi had some of the best Tucson wines we have ever had. We even ordered some for our son’s wedding this summer! We would highly recommend We Drive You Tuscany!
          Written May 7, 2023
        • ClaPoh
          0 contributions
          5.0 of 5 bubbles
          Glad to have Engaged We Drive You Tuscany!
          Am so thankful that I chanced upon We Drive You, Tuscany on Trip Advisor! Initially, my plan was to self-drive.. but decided not to because I want to take the beautiful pictures of the rolling hills and drink! In total, we engaged the service for 4 days, out of which - 2 full days visiting different areas such as Pienza, Montepulciano, Montalcino, Cortono and the nearby attractions etc. Blessed to have Roberto be our friendly driver. He plans his daily schedule very well and makes sure the place we visited, including F&B are well taken care of. We chit chatted during the drive and the chat made me understand more about these places and some of the history. Roberto also makes sure communication never ceased. He will share precise information about the meeting points and times; knowing sometimes we the tourists are unaware of the locations. Both me and my son felt that throughout the trip, Roberto is more than a driver. He was like our guardian in Siena. Were kind of sad and loss when we were left on our own in the next city. Haaa. But all is well. Thank you, We Drive You Tuscany and Roberto for giving us such memory of Siena + Tuscany. Will be back!
          Written January 24, 2023
        • sandralL2202JL
          0 contributions
          5.0 of 5 bubbles
          Customised itinerary experience
          Roberto is a friendly driver with good local knowledge. Prompt arrival, clear communication, careful driving, and a comfortable car made for a most enjoyable day. Thank you, “We Drive You Tuscany”, for accommodating our custom itinerary.
          Written December 25, 2022
        See all 172 reviews
        These reviews are the subjective opinions of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

        Most Recent: Reviews ordered by most recent publish date in descending order.

        Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

        Popular mentions

        5.0
        5.0 of 5 bubbles19 reviews
        Excellent
        18
        Very good
        1
        Average
        0
        Poor
        0
        Terrible
        0

        Zuli
        1 contribution
        5.0 of 5 bubbles
        Dec 2021
        We booked a tour with Tomas during our vacation last December and, even though the weather was not on our side, it was the highlight of our trip. Tomas was very knowledgeable and friendly. We visited two local wineries, had an amazing lunch at a farm, and had a very enjoyable walk through Pienza. We are hoping to go back and will definitely reach out to Tomas/We Drive You Tuscany. We highly recommend their tours to anyone who is looking to have a great unique experience.
        Written June 20, 2022
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        Thank you for the nice review. We can not control the weather, but we know Tuscany is still beautiful no matter the weather. We are glad you enjoyed your tour, and we hope to see you again to discover more of Tuscany. Grazie
        Written August 4, 2022
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        Steens
        Fort Myers, FL12 contributions
        5.0 of 5 bubbles
        Sep 2022 • Couples
        Amazing experience. The wineries were incredible at explaining wines, the process, types, etc. The wines themselves were lovely. We couldn’t have asked for a better, exclusive wine tour experience.

        Our tour guide, however, made the entire experience worth it. He made stops for photos, custom for routes based on our interested, and even made recommendations for places for us to go the following day on our own.

        Amazing.
        Thank you!
        Written September 18, 2022
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        We are pleased to hear that you enjoyed the tour and the boutique wineries we took you to.
        Written October 5, 2022
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        Meredyth
        1 contribution
        5.0 of 5 bubbles
        Sep 2022 • Friends
        This wine tour was fantastic! We visited two delicious wineries, had a great lunch and shopped in the afternoon due to rain. Our driver, Davide, was amazing and so accommodating to our needs. Highly recommend this tour!
        Written September 26, 2022
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        We are glad that Davide made sure you had a good time, even if the weather wasn't perfect. Thank you for recommending us!
        Written October 5, 2022
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        Diane T
        5 contributions
        5.0 of 5 bubbles
        Sep 2022
        This was such a beautiful drive! The scenery was breathtaking! Guglielmo (William) was a very good driver. He was very knowledgeable, pleasant and witty. I would highly recommend this trip again with him as a guide!

        The cheese tasting at the organic cheese farm was delicious. I loved the visit to Pienza, such a beautiful village! We had a delicious lunch there. And the drive through Val d'orcia to Montalcino was lovely. The Montalcino wine at Casanuova delle Cerbaie, which had the delicious brunella wine of Montalcino.....well this was a favorite part of the trip. Thank you to Guglielmo for making this the most wonderful tour for our last day in Tuscany!
        Written September 17, 2022
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        Thank you for such a nice review. We are happy to hear that you enjoyed the day and all the places that you visited. The Val d'Orcia is definitely one of the most beautiful parts of Tuscany! Ciao
        Written September 18, 2022
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        Sutton W
        Raleigh, NC5 contributions
        5.0 of 5 bubbles
        Apr 2022 • Friends
        Tomas is the very best at what he does. He was our driver and guide yesterday in Tuscany. We did the wine tours, and visit to Pienza. He was absolutely what we had hoped for. As a local, he took us to places that were special to him in hopes we would feel the the passion he had for the area. The wine makers and locations he took us to were absolutely perfect, quaint and unique. He was so patient- as we ran a few minutes late for pick up. He’s was very informative, engaged and wanted to make sure we were happy, comfortable etc. He also takes you to the most beautiful spots for pictures throughout the day. Not to mention our fabulous lunch experience at an organic farmhouse. If you can book with Thomas it will be the experience of a lifetime!
        Written April 13, 2022
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        Hello Sutton, Richard and Patty. It has been a great, great, great pleasure for me to drive you around the Montalcino wine area, the Val d'Orcia and Pienza UNESCO sites. I was happy to introduce you to our friends Alessandro, Dario and Davide in Tuscany and to give you a taste of the local, authentic "Dolce Vita". We hope to see you soon, but next time with more days, to show you other secret gems and more of our friends. Look forward to seeing you soon. Keep in touch. Ciao!! Tomas
        Written April 14, 2022
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        krm411
        Idaho2 contributions
        5.0 of 5 bubbles
        Sep 2023 • Family
        We had an amazing time with our guide Roberto! He made the trip so much fun! Great humor, a wealth of knowledge, and so easy to work with. The wineries were perfect, the wine was fabulous and lunch was fantastic. If I could give Roberto an even higher rating I would!!!
        Written September 9, 2023
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

        jmb3535
        Denver, CO3 contributions
        5.0 of 5 bubbles
        Sep 2022
        We loved the Val d'Orcia tour with Davide! It was a terrific way to spend the day seeing the county side and learning about the area. Davide was knowledgeable and fun. The tour was a top experience durning our stay in Siena.
        Written September 11, 2022
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        Thank you for the review. We are happy to hear that you had a good day and enjoyed the experience with Davide in the Val d'Orcia.
        Written September 12, 2022
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        Km
        Irving, TX1 contribution
        5.0 of 5 bubbles
        Amazing!!! 6 out of 5 stars! We took the Chianti Classico and Val d’Orcia tours and both were wonderful! Roberto and Davide were the perfect drivers, tour guides and hosts. They were so knowledgeable and engaging, and made the day fun. We wouldn’t have been able to see so much of Tuscany on our own. They know all the best places and boutique wineries, including small wineries that have been in families for generations. Don’t go to Florence without seeing other parts of Tuscany. Book these trips!!
        Written September 14, 2022
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        Grazie!!! Thank you for the kind words. Roberto and Davide are great guides. They certainly love their jobs and Tuscany. We like to give our clients an authentic experience of Tuscany, to meet our friends. Passionate and local food and wine producers. We are glad you enjoyed your time in Tuscany. And we agree there is more to Tuscany than Florence : )
        Written September 14, 2022
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        Ray E
        Birmingham, AL46 contributions
        5.0 of 5 bubbles
        Oct 2017 • Couples
        This was not this exact tour, but even better. My wife and I were in Cortona on a 12 day Italy tour. We love Brunello's and had a tasting already set up. We thought about driving ourselves, and we are GLAD we didn't! Tomas knew the roads like "the back of his hand". We didn't have to find a way to Siena, as he picked us up at our villa in Cortona. He worked around our 300pm tasting with a tasting at Podere Le Ripi, a small organic winery exploring new techniques and a Fabulous lunch at Trattoria Leccio. Excellent English skills and even a better personality. Would travel with him again.
        Written October 21, 2017
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

        Eric F
        2 contributions
        5.0 of 5 bubbles
        Apr 2019 • Couples
        My wife was kind enough to book this for my birthday and it was an incredibly memorable experience. Our driver, Roberto, took us around in a comfortable Mercedes van through the region of Brunello and took excellent care of us. Excellent English, super personable and extremely knowledgeable about wine, Italian culture, and beyond.

        While there's a tentative itinerary outlined in advance, the day was flexible and we adjusted accordingly as our visits to the wineries went longer than expected (as we were enjoying ourselves so much!). Our lunch stop was just as memorable as we were taken to a small family farm where we had a chance to meet the family members during our meal.

        It was a huge stress relief to not have to worry at all about driving on our own and likely having to fumble our way through finding different wineries. I cannot recommend this private tour more for anyone who's interested in exploring the wines of Tuscany!
        Written April 15, 2019
        This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
        Thank you for the very nice review. It always makes us proud when we receive such feedback. I have passed on the review to Roberto and the team. Thank again, we are glad you enjoyed your time in Tuscany with us.
        Written May 13, 2019
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        Showing results 1-10 of 14

        Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA provided by We Drive You Tuscany

        Product Overview: Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

        Prices From

        $485

        Number of Reviews

        19

        Number of Photos

        20

        Duration

        480 minutes