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

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

From $589.34 per group (up to 7)

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Free cancellation
Up to 24 hours in advance. Learn more
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icon8 hours  (approx.)
Hotel pickup offered
Mobile ticket
iconOffered in: English and 3 more
Good for avoiding crowds


Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable private driver, travel through the renowned Chianti wine region to visit the towns of Siena and San Gimignano. See famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano.
  • Take a full-day private tour of Tuscany from Florence
  • Sample Chianti wine at a local vineyard
  • Visit the medieval city of San Gimignano and Siena
  • A private guide and vehicle ensure a personalized experience
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Hotel pickup and drop-off in Florence
Private luxury minivan
Bottled water
Onboard Wi-Fi (on request at reservation)
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.
Spanish-, Portuguese- or French-speaking driver upon request
Lunch + wine tasting at farm house (to be paid on spot)
Guide city tour (you will find the complete tour with private guide in Siena on viator with this code 23322P50)

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9:30 AM
Pick up from all hotels or apartments in Florence downtown
  • Confirmation will be received at time of booking
  • Infant seats available
  • A maximum of eight people per booking
  • Not wheelchair accessible
  • Stroller accessible
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate
  • OPERATED BY Chianti Drivers private tours
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, you must cancel at least 24 hours before the experience’s start 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.

Learn more about cancellations.

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Traveler Tips

  • "Highly recommend this private tour so you can spend the time you want along the way!" See review


88 Reviews
3 stars
1 star

Reviews by Viator travelers

Showing 1-10 of 88 reviews
Great Sightseeing with Good Wine
, May 2022
Loved the tour. Maximo was a great driver; he was a local, so was very knowledgeable of the area and history.
Simone was an amazing...
, May 2022
Simone was an amazing driver for our tour & friendly! He gave a lot of information about San Gimignano and Chianti. & we had some great sights along the way
10 out of 5 stars!!!
, May 2022
Amazing, beautiful, unforgettable trip. We loved it...Andrea was knowledgeable, friendly and super cool. We took this trip with our 3 year old daughter and had the best time. :)
Best part of our visit to Italy
, May 2022
Massimo our tour guide was so knowledgeable about the areas and the history the entire day was a a very enjoyable experience
Barbara is wonderful
, May 2022
We were absolutely charmed by Barbara our guide, so knowledgable and exuberant about her home town. We can’t recommend her enough. Comfortable clothing a must, it’s a long day. David is so worth the visit. He and all of the other works of art we saw deserve reverence. Shame about all the “selfie takers” 😡
Wonderful day…
, May 2022
Simone was a wonderful driver/guide for the day. He gave us information about each location we stopped at. We had free time to explore. It was an extremely flexible day. He even took us to a few extra stops on the way back to Florence.
Excellent Tour!
, May 2022
Hearing history of the area from our fantastic/driver, Ricardo. Having a wonderful lunch with lots of great food and wine! Seeing the beautiful Tuscan countryside and Siena and San Gimignano. Everything was excellent all day!
1 traveler found this review helpful
Highly Recommend! A wonderful day outside of Florence
, May 2022
Massimo was a wonderful guide and driver for the day. He gave us plenty of information and was extremely flexible throughout the day. He was so friendly as well. He also organized the perfect lunch and wine tasting in between our stops. My wife and I would highly recommend this to anyone.
Authentic Tuscan experience
, Apr 2022
The farmhouse restaurant/winery we went to was beautiful with great wine and food- felt like a real Tuscan experience! I do wish my driver’s English was a little better
Wonderful day trip from Florence
, Apr 2022
We had a fabulous experience on our private tour! What a fantastic way to get a taste of Tuscany - our driver, Massimo, was incredibly knowledgeable and made great suggestions for how best to use our limited time in each place. He was also very flexible and gave us options so we could do exactly what we wanted to do. The van was incredibly comfortable and Massimo was a safe driver. Perfect day trip!

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