Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence
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Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

By Chianti Drivers
Recommended by 100% of travellers
100% of reviewers gave this product a bubble rating of 4 or higher.
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Lowest price guaranteeReserve now & pay laterFree cancellation

Ages 0-99
Duration: 8h
Start time: Check availability
Mobile ticket
Live guide: English, Italian
More


  • Hotel pickup and drop-off in Florence
  • Bottled water
  • Onboard Wi-Fi (on request at reservation)
  • Private Guide in the wine cellar
  • Private Guide in the city of Siena
What's not included
  • Lunch
  • Gratuities
  • Museum/churches fee
  • Entry/Admission - Tenuta Casanova


Start:Multiple pickup locations offered.
    Pickup details
    • Pick up from all hotels or apartments in Florence downtown
    Hotel pickup offered
    During checkout you will be able to select from the list of included hotels.
      End:This activity ends back at the meeting point.

        • Not wheelchair accessible
        • Infant seats available
        • Pushchair accessible
        • Near public transportation
        If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 23322P50

        • Confirmation will be received at time of booking
        • A maximum of 7 people per booking
        • Drivers are all extremely familiar with Tuscany and with the main destinations in Italy. They will always share information, curiosities and traditions about the area of the sightseeing and they are available at any needs.
        • Most travellers can participate
        • This is a private tour/activity. Only your group will participate

        • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

        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: 23322P50

        From
        $1,648.40
        per group (up to 7)
        Select date and travellers

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        About the operator
        Don’t take it from us – here’s what people have to say about this operator:
        • Chianti Drivers
          175
          Florence, Tuscany, Italy
          Joined in May 2020
        • DONALD S
          0 contributions
          3.0 of 5 bubbles
          Family Vacation
          Wine Tasting was excellent. However when booking need to be clear that private tour was only driver …NOT someone who could explain and give detail about areas we visited . We assumed private was that . Michael the driver was good but we had thought the driver would give overviews
          Written 25 November 2024
        • JocieSch
          0 contributions
          5.0 of 5 bubbles
          Our Favorite Day in Tuscany!
          Our favorite day in Florence! Simone was an absolutely wonderful tour guide! We were promptly picked up at 9:30. Spent approximately 2 hours in Siena. Had a wonderful lunch, wine tasting and cellar tour at Casa Emma with amazing and beautiful views. Ended in San Geminigno and totally enjoyed ourselves. I highly recommend this private tour for your small group!
          Written 10 October 2024
        • maed395
          0 contributions
          5.0 of 5 bubbles
          Definitely worth the money!
          The experience was amazing, very prompt, Siena and San G beautiful. The ride was comfortable and Sam was extremely Knowledgeable. The winery was so delicious and educational
          Written 19 September 2024
        • K2235BBreginac
          0 contributions
          5.0 of 5 bubbles
          Truly special experience
          This was an outstanding day trip. Luigi is simply amazing. I’m sure we never would have found the wonderful family winery where we tasted wines and had a delicious lunch without his help. And at the end of our trip Luigi handed us a bottle of wine! Certainly the highlight of our trip thus far.
          Written 18 September 2024
        • K5361TZalexanderh
          0 contributions
          5.0 of 5 bubbles
          Good Driver, I’d skip Siena
          The driver (Azzari) was prompt, professional. and made sure we got to see all destinations and went overtime to accommodate us. We opted for the winery stop and although it was not the most beautiful winery, the wines were great (a bit pricy though). Personally, I would skip Siena unless there is something specific there you want to see as we stayed in Florence and felt that it was very similar, it was also the farthest destination. San Gimignano was a wonderful stop and our favorite!
          Written 8 September 2024
        • Ltrichert
          0 contributions
          5.0 of 5 bubbles
          Must do tour
          What an amazing day! Simone is a professional & informative tour guide and 100% recommend him and this tour. We loved the medieval towns and had a fantastic lunch/wine tasting @ Casa Emma.
          Written 5 September 2024
        • francescagJ5416AH
          0 contributions
          5.0 of 5 bubbles
          Highly Recommend!
          The trip was amazing and very worth while. We saw amazing views within the 2 villages as well as a great experience at a family owned winery. We highly recommend Gino as your tour guide. He was very friendly and always helpful with extra information and even made a special stop at the US cemetery for us to visit. Accommodations were great, air conditioned, clean and beautiful van.
          Written 9 August 2024
        • cabebe
          0 contributions
          5.0 of 5 bubbles
          Excellent Tour
          Massimo was a great tour guide. Drove safely, knowledgeable about the area, and very easy to talk to. He pointed out important landmarks and things we should experience. Definitely would recommend this trip to Sienna and San Gimignano and Chianti!
          Written 31 July 2024
        • marktbright
          0 contributions
          5.0 of 5 bubbles
          great trip through Tuscany
          Great tour, so many photos. Sienna and San Gimignano are amazing and the winery was perfect. Having Simone as a private driver was fantastic, he was very informative and made sure we had a great experience at our own pace. Highly recommend.
          Written 16 July 2024
        • Navigate04602767100
          0 contributions
          2.0 of 5 bubbles
          It doesn't have much value!!!
          My daughter and I were on holiday in beautiful Tuscany and we traveled a lot. Given the wonderful experience in Cinque Terre the year before, we thought about buying a tour in Tuscany This time too our driver showed up with a beautiful and good quality car but he spoke little and his English was a little tired, he laughed a lot and I don't know how much he understood what we asked of him. We had no information about Sienna and Sangimiano. The service for the cost is a bit of a tourist trap like lunch in a place with a lot of people, the wine very expensive. Not worth the money we could have rented a car.
          Written 16 July 2024
        • nhbellingrath
          0 contributions
          5.0 of 5 bubbles
          Excellent
          What a wonderful day. Simone was our driver and he is absolutely wonderful. The country was beautiful and just an incredible day !!
          Written 4 July 2024
        • Nomad28000582185
          0 contributions
          5.0 of 5 bubbles
          Excellent wine day in the Tuscan countryside
          To start, Max was amazing. He was so kind and knowledgeable about Florence and the wine region. He took us to every sight and lookout to ensure the best experience. We loved both vineyards he chose for us. The town of San Gimignano was an absolute dream. Highly recommend this company for your trip. Sabrina was extremely professional and quick in communication. Max, we love you and will forever remember our experience!
          Written 25 June 2024
        • CoachEtravels
          0 contributions
          5.0 of 5 bubbles
          This was the best experience of our entire trip to Italy!
          This was the best experience of our entire trip to Italy! Simone was amazing! He was punctual, extremely knowledgable, and very kind! He took us on the backroads to the vineyard and it was absolutely breathtaking!!! Honestly the scenery and the small, ancient towns were so lovely. Simone was fun and knew all the hidden spots so we took many spontaneous detours that really made the day special :) Casa Emma wine tour was amazing as well. All in all best day in Italy, I highly recommend!
          Written 9 June 2024
        • Jennifer F
          0 contributions
          5.0 of 5 bubbles
          Great day!
          Great time had by all! Maurizio, our driver, did a great job telling is about the countryside. The drive was amazing! The lunch was fabulous!
          Written 23 May 2024
        • joannelM569AG
          0 contributions
          5.0 of 5 bubbles
          Tuscany day trip from Florence
          This was such an amazing day trip of Tuscany! Many thanks to our driver Michele who was knowledgeable and gave us an opportunity to take memorable photos! Our lunch and wine tasting with Francesco at Corbucci winery was the highlight of our trip! We will definitely recommend this intimate experience to all of our friends and family.
          Written 19 May 2024
        See all 175 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 waiting time, length of visit, general tips, and location information.

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        5.0
        5.0 of 5 bubbles11 reviews
        Excellent
        10
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        1
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        0
        Poor
        0
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        0

        klam0719
        Centerport, NY6 contributions
        5.0 of 5 bubbles
        Our day in Tuscany was the highlight of our Florence trip. Cosomo was our driver and he was a pleasure to spend the day with. He drove us to Siena where we had a city tour with Vivianna. We were lucky enough to see the city set up for the Palio horse race which was two days away. The flags of the districts were on every corner and it added to the experience of learning what life inside Siena is like. Cosomo make reservations for us at Tenuta Casanova winery for a tour and lunch. The price is not included in the tour but I highly recommend including this in your day. The owner himself showed us around his winery and our wine tasting lunch was one of the best meals we’ve had in Italy. Last was an hour in San Gimignano, without a guide. I wished for more time here but we had a quick walk through and some amazing gelato at Gelateria Dondoli. I would love to go back and climb the towers one day. Overall a fantastic experience and I would highly recommend.
        Written 3 July 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.

        yobisss
        Valley Cottage, NY90 contributions
        5.0 of 5 bubbles
        We had an absolutely fantastic time. Two couples visiting from the United States. Simone, our driver, could not have been better. His knowledge was excellent. He took us on back roads and pointed out so many things we never would’ve gotten to see otherwise.

        The visit to Casa Emma Winery was above par and the food was excellent. The wine was quite tasty and the winery was absolutely beautiful.

        We highly recommend this company for a tour.
        Written 12 April 2024
        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.

        Tracy T
        1 contribution
        5.0 of 5 bubbles
        Oct 2023 • Couples
        Our trip with Marco was beyond what we expected from this private tour. He was knowledgeable, friendly and was a great guide, as we are first timers to Italy and unsure of the region we were visiting. The winery was great and loved visiting the other villages.
        Written 16 October 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.

        Sarah N
        2 contributions
        5.0 of 5 bubbles
        Jun 2022 • Family
        Our trip was so amazing because of Marco. He was very friendly, and took us/ recommended us to beautiful places in all of the cities. He was very friendly and we had so much fun. He took us to a beautiful winery overlooking the hills of Tuscany and it was the highlight of our trip. This tour is perfect for whoever wants a more private experience of the beautiful cities in Italy. Highly recommend Chianti Drivers! Hope to see Marco again soon for more tours!
        Written 19 June 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.

        Joanna J
        3 contributions
        5.0 of 5 bubbles
        Mar 2024 • Family
        Highly highly recommend booking this tour! My family and I were celebrating my mom's 50th birthday in Italy and we booked the private day tour with our driver Simone. Not only did he show us the beautiful hidden sights of Tuscany, but he was also a very kind and fun guy to spend the day with! Despite the rainy day, we had a wonderful time. Delicious wine tasting and lunch at Casa Emma. Thank you again Simone for the wonderful experience! :)
        Written 30 March 2024
        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.

        T. Mazzaro
        1 contribution
        5.0 of 5 bubbles
        Feb 2020 • Family
        Alessandro took us on a lifetime experience private tour. He knew everything, gave us the good spots to visit and brought us to the Casanova farm in Tuscany which was incredible. Alessandro brought my family and I to Siena, Tuscany and San Gimignano. All of this in 9 hours. He was the BEST guide we could’ve received and I will 100% be back for another tour with him. Again, the best day of our trip and I will be recommending him to anybody that is in the Florence area for the day. 10/10. Thank you Alessandro for making our trip unforgettable!
        Written 16 February 2020
        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.

        mdsilvas2000
        Cambria, CA4 contributions
        5.0 of 5 bubbles
        May 2019 • Couples
        the city tour of sienna was excellent, including walk through modern city grocery market with aromatic cheeses, meats and endless wines. We were sorry couldn't linger and buy.I personally have seen sienna before, but got a better appreciation with guide's(I cannot recall her name for sure) pointing out of highlights. Simone was professional and did much to make the drive enjoyable. I even enjoyed hearing about his family which gave us a feel for family life in Florence.
        The rushed time in san gimignano was almost more of tease than enrichening.
        The winery tour was beautiful setting, and wowed some of our roup. but felt more of a "Sales call" with slightly dragged out lunch. I would have liked to hear more about wine production to compare with what I know about california winemaking. the wines and basalmic were excellent.
        Written 11 May 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.
        Thanks so much!
        Written 29 May 2019
        This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

        VBR0122
        Marikina, Philippines2 contributions
        5.0 of 5 bubbles
        Very efficient Driver and Tour guide. Simone was very good. I would definitely recommend to my friends and family visiting Florence
        Written 30 March 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.

        John C
        1 contribution
        5.0 of 5 bubbles
        May 2022
        In early May we had the pleasure to take this trip provided by a wonderful fellow by the name of Max. Highly recommend!
        Written 21 June 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.

        Deb07
        1 contribution
        5.0 of 5 bubbles
        Sept 2019
        Simone Mazzini was amazing! So pleasant, polite, informative, funny and just a wonderful man. He took us to three wineries and each one was so very special. He even stopped on the way to take pictures of the six of us overlooking Florence. He had the patience of a saint! I would highly recommend him and Chianti Drivers.
        Written 2 October 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.
        *Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.

        Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence provided by Chianti Drivers

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