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

icon 8 hours Mobile ticket Free Cancellation
Tickets from € 1,104.00

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*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni (just if you won't need a stop for lunch) and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * Would you like to have a traditional Italian meal’s experience? We can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lovers.
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  • expert english speaking driver
  • Our 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.
  • Bottled water
  • Onboard Wi-Fi (on request at reservation)
  • Air-conditioned vehicle
  • Hotel pickup and drop-off in Florence
  • Private luxury minivan
  • Lunch + wine tasting at farm house (to be paid on spot) around 40/60 euros per adult
  • mance
Departure Point

Traveler pickup is offered

Pick up from all hotels or apartments in Florence downtown

  • Siena, Siena, Italy
    Siena is known throughout Italy for the quality of its medieval architecture. Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the outstanding 13th-century Siena Cathedral. Many local shops fill the historic streets of Siena that will allow you to taste or taste local food or buy some gifts!
    120 minutes
  • Castellina In Chianti, Castellina In Chianti, Italy
    *Option to organize lunch at the Farm or Winery, where you can taste wines and organic local products. (to be payed on spot) (This option will reduce the time in the cities of Siena and San Gimignano and exclude Monteriggioni).
    120 minutes
  • Chianti Road, Italy
    We explore the country of Tuscany, we will drive through the chianti hills. Stop for picture!!!!
  • Historic Centre of San Gimignano, San Gimignano, Italy
    Here we are in the beautiful stronghold of San Gimignano. Freeze at the age 1300dc, San Gimignano a pearl of medieval architecture famous for its houses tower! This is our last spot of the day before returning to Florence
    120 minutes
  • Specialized infant seats are available
  • Infants and small children can ride in a pram or stroller
  • Suitable for all physical fitness levels
  • A maximum of seven people per booking
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
Robert_K
31 Mar 2025
Simone, our private guide, was wonderful. He took us to three hilltop towns in Tuscany: San Gimignano, Monterrigioni and Sienna. Each beautiful and distinctively different. SImone was very knowledgeable of each town and Tuscany in general. Additionally, he was flexible in modifying the itinerary to meet our goals. It was a joy to spend the day with him and was a highlight of our two weeks in Italy. We highly recommend Simone.
Heather_C
29 Mar 2025
Wonderful experience. Mossimo (our driver) picked us up right at our Airbnb and allowed us to add a stop at the Florence American Cemetery and Memorial, which we greatly appreciated! He was an excellent tour guide who gave us plenty of history for each stop, and respected our time in each area, making sure that all members of our party were comfortable. I would highly recommend this day trip from Florence as a lovely break from the city.
DayTrip733480
27 Mar 2025
We had a great day seeing Siena and San Gimignano! Marco was our driver who was wonderful and shared his knowledge about the Siena horse races! It was so interesting! We stopped in Siena and then had lunch at a winery which was amazing. Francesco was so passionate about winemaking and made our time so special. It was the highlight of our trip. We finished the day in the small village of San Gimignano. It’s a great way to see the small towns around Florence! I would definitely recommend this trip!
This tour in Florence is organized by Chianti Drivers private tours

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We always double-check the availability with our local partners for each booking. Even though this is usually a swift process, it can take up to 24 hours. Once this process is completed you will receive your voucher or ticket by email. If our local partner is not able to confirm your booking we will offer you the best possible alternative. If the new date and/or time doesn’t fit your itinerary, we will reimburse the full amount paid.
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