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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 $580.57 per group (up to 7)

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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

After booking, the operator will contact you about pickup time.

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


57 Reviews
3 stars
1 star

Reviews by Viator travelers

Showing 1-10 of 57 reviews
Simon was extremely...
, Oct 2021
Simon was extremely professional, kind and attentive. He took us on a wonderful tour around Tuscany visiting some amazing sights, views and tastes. His driving is superb and added some great information about the region as well. A great way to spend the day and adventure outside of Florence.
Wonderful day in Tuscany
, Oct 2021
Max, our driver, was wonderful. He was incredibly friendly and very knowledgeable about the region and it’s products.
Perfectly wonderful.
, Sep 2021
Simone, our driver and guide was a gentleman's gentleman. He shared his knowledge but also knew when to leave us alone. First, he took us to San Michaelangelo plaza to see all of Florence glory. Then we went to San Gimignano, Siena, and lastly, Monteriggioni. All had their history and charm. We weren't rush and Simone even made reservations for our lunch at La Finestra in Siena. The Mercedes van was immaculately clean and comfortable. Visiting these places from Florence is the only way to go if you desire a very relaxing and comfortable day trip.
The Tuscan Countryside Didn’t Disappoint
, Sep 2021
What a day! Our guide Simone was great! He had some tough shoes to fill after the amazing walking tour we had the previous day and he was just as good. We were picked up at our hotel right on time, he was there a few minutes early. At the start we told Simone that we wanted to indulge in Tuscan wine throughout the day. Simone delivered! Before we left Florence we made a stop to take awesome pictures that were not on the schedule but Simone accommodated us. We started the tour in Sienna and saw the shops and the square. From there, Simone was working in the background to arrange a wine tasting and lunch. He did just that! We went to a local winery with rich history and amazing wine! And we had a lot of it! We had a great lunch as well. From there, Simone gave us the option of continuing to San Gimignano or going on another wine tasting! Our guide was so flexible and accommodating. Interestingly enough, we chose to go San Gimignano and see the sights and ultimately eat gelato which we even got great recommendations on as well. It was an amazing day, well worth the money and Simone was awesome. Highly recommended.
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!
1 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.
3 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.

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