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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.
Terri_L
12 Aug 2025
Our driver & guide picked us up at our hotel and we set off to see Siena, San Gimignano, the countryside and had lunch at a lovely winery. It was a fun, relaxing and informative day. We learned quite a bit about Italian culture and the economy. We were dropped off in the center of Siena, outside the main gate at San Gimignano and had free time to wander, get gelato, and shop. There wasn't time to pop into museums or tour the churches but you could do it if you were quick. Our side quest to a winery was a magical experience. The winemaker greeted us like family and we had a wonderful time learning about their history, the wines, and enjoyed a simple but tasty lunch while we sampled all the wines. It was only our group of three and another couple, so it didn't feel at all like we were part of a mass tour. It felt very personal. At the end of the tour we were taken back to our hotel and we all agreed it was a great way to spend our last day in Florence.
Riley_C
23 Jul 2025
We had the best time with Massimo on this tour!! He was extremely accommodating and flexible. He let us stop for scenic photos multiple times, even when it was complicated and he had to go around a one way street to be able to stop us for the photo. He was very informative without giving us too much information — just the right amount! He was truly a delight and made our day. The itinerary was good, though we wish we had more time in San Gimignano. The winery, Casa Emma, was delightful! We did a full tasting and bought some lovely wine and olive oil. It was truly a great day and we have Massimo to thank!!! It’s an expensive tour but worth it to be navigated directly to the villages without any hassle. 10/10 would recommend!
R230GCrons
16 Jul 2025
Our guide Massimo was amazing. He was very knowledgeable and willingly shared the history of the area as he drove to the various destinations. The wine tasting and lunch at a small family operated vineyard was absolutely perfect. This trip was definitely a highlight on our two week vacation to Switzerland and Italy.
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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