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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 $584.69 per group (up to 8)

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Free cancellation
Up to 24 hours in advance. Learn more
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icon8 to 9 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 in winery or farm. (to decide at the time of briefing in the morning with your driver)
Guide city tour (you will find the complete tour with private guide in Siena on viator with this code 23322P50)

Departure Point

Traveler pickup is offered
Pick up from all hotels or apartments in Florence downtown

Departure Time

9:30 AM
  • 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

For a full refund, cancel at least 24 hours in advance of the start date of the experience. Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the maximum group size during Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence?
A:This activity will have a maximum of 8 travelers.

See all safety measures taken by Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence.

Traveler Photos

Traveler Tips

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


51 Reviews
3 stars
1 star

Reviews by Viator travelers

Showing 1-10 of 51 reviews
Incredible Day
, Sep 2021
Gino was amazing! He was knowledgeable, courteous, interesting and couldn’t possibly do more to make our trip the wonderful experience that it was. We had reservations for lunch in Siena and he happily tailored the day around our plans. He pointed out interesting sites along the way, suggested a place for the best gelato in San Gimignano, best we’ve had in Italy actually, and bought us some delicious almond cookies to enjoy at the end of our day. Truly a memorable experience.
Fabulous Private Tour in the Tuscan Coutryside
, Aug 2021
We had a wonderful day with our guide, Fabrizio. Fabrizio was superb! He provided gentle instruction throughout the day as well as accommodated our whims. He has such a kind demeanor. We started our day with a beautiful drive to Siena which is a lovely small town you can “tootle” in an hour or so. We then traveled to our lunch destination which was a working farm/winery with magnificent views and rural touches i.e. peacocks, chickens and their offspring meandering nearby. The lunch far exceeded our expectations as well as the wine pairings, tour of the winery and gracious hosts. Lunch was served in three courses in typical European fashion, slow and relaxing…as there is no other place you’d rather be. We gathered ourselves to head to San Gimignano but we decided to work our way back to Florence since it was getting close to our days end. Perhaps a quick briefing in advance would allow for a more scheduled day to fit it all in…but we were quite happy to let the day happen without tight scheduling. This is truly a unique experience and a must do!
HelpfulHelpful1 traveler found this review helpful
, Jul 2021
Outstanding experience. Mossimo was an excellent guide and driver. Don’t miss this tour. Breathtaking.
a one of a kind experience
, Jul 2020
This private tour is the best romantic experience you can have in the wonderful Tuscany and Alex provides an outstanding flexible tailor made experience, for sure it is something we will do again.
icon Response from Host , Dec 2020
Hi Jean thank you for the review and hope you are well and safe. Thanks again and regards Sabrina
Lunch at Monteggiamo
, Jan 2020
My husband and I had an amazing trip, thanks to our guide Alex. He was extremely flexible with the itinerary. We hadn't done much research ourselves, and were completely counting on him to help us out with options. We were more interested in seeing the villages and enjoying scenic landscape, over a wine tour,and keeping that in mind, Alex helped us chart out our days plan that ended up being the highlight of our italy trip. He was so flexible, that he even allowed us to spend more time at San Gimignano even though the trip was only supposed to be 8 hrs long. It was truly a memorable day.
HelpfulHelpful3 travelers found this review helpful
Last Minute Tour
, Dec 2019
Our trip with Simone was excellent. I booked a last minute tour to Siena, San Gimignano and Chianti and was amazed at how everything went without a hitch. Simone was very nice and knowledgeable. He took us to great restaurant for lunch where we had a wonderful time. Opted for a wine tasting stop and it was also awesome. Highly recommended. We were party of 8 and tour was on Dec 04’19.
Excellent Tour - must do!
Tricia C
, Nov 2019
This tour is amazing! Massimo was our guide, he was excellent I highly recommend him! The great thing about a private tour is that you can customize it, and Massimo did a great job of that! I explained to him that I love photography and I am not as into sitting around wine tasting, so he customized the tour and we skipped that sit down lunch that would have used maybe 2 hours and instead did a quicker lunch in Siena, so that we had more opportunities for scenic photo stops along the way! Superb! If I book this tour again to see new places, I will definitely request him! Tricia
HelpfulHelpful1 traveler found this review helpful
Amazing Views, Great Wine, and a Fantastic Host
, Oct 2019
My wife and I did this tour with our host named Alessandro. It's incredible. The views are breathtaking and every recommendation from Alessandro was perfect. We visited several towns and he also took us to a wine tasting at a vineyard with some of the best food and wine we've ever tasted. We will do this trip again when we return.
HelpfulHelpful1 traveler found this review helpful
A wonderful wine tasting experience in Tuscany
Paula V
, Oct 2019
From start to finish this was a very special wine tasting tour. Our guide was very knowledgeable and took us to some very interesting places in Tuscany to savor not only delicious and very special wines but also amazing home cooked meals. We had a thoroughly enjoyable day.
, Oct 2019
This tour was wonderful! We went to Siena, a winery for lunch and tasting and then San Gimignano. He even took us by Piazza Michelangelo on the way back to our airbnb and got some great photos for us. Gino went above and beyond to make sure our trip was perfect. I would definitely recommend this tour!

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