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

Florence, Italy
Siena San Gimignano and Chianti Countryside

From $698.92

per group (up to 7)

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 8 hours
  • Pickup offered
  • Mobile ticket
  • Offered in: English


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

What's Included

  • 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)

Meeting And Pickup

Pickup points

Select a pickup point

Start time

09:30 AM

Pickup details

Pick up from all hotels or apartments in Florence downtown

What To Expect


2 hours Admission Ticket Free

Castellina In Chianti

2 hours Admission Ticket Free

Chianti Road (Pass By)

Historic Centre of San Gimignano

2 hours Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Infant seats available
  • A maximum of seven people per booking
  • Not wheelchair accessible
  • Stroller accessible
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate

Cancellation Policy

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.

Traveler Photos

See more

Traveler Tips

Highly recommend this private tour so you can spend the time you want along the way!


212 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 212 reviews
Michele in the best!
Irene_G, Sep 2023
Amazing Day! Our driver & tour guide, Michele, was so informative & great fun. We had a wonderful time & will treasure the memories forever. Not only did he show us Siena, San Gimignano, & many breath-taking views of Tuscany, he also gave us lots of recommendations for our time in Florence! Thank you Michele, from the bottom of our hearts. We loved every minute, especially the wine! Irene, Kay & Mumma xxx
Family vacation
brenda_T, Sep 2023
Our tour guide Massimo was amazing!! We originally booked our tour with another company that arranged lunch for us and Massimo called the farm/vineyard to confirm our lunch and still made sure we saw everything.
The MAX experience!
Lori_C, Sep 2023
Max was great! He made sure we were comfortable.. He took extra effort to stop for photos and shared a lot of regional tidbits of information that were interesting and educational to the area. Beautiful day!
Perfect day out from Florence
Lisa_R, Sep 2023
The whole day was fantastic. Our driver/guide was Simone and he took us to the best spots for photos of Florence Siena and San Gimignano. The lunch and wine tasting he arranged was perfect. The trip was full day and worth every penny. Made lots of happy memories
Barbara_B, Aug 2023
Simone was personable, informative and such a good guide/driver. We would definitely recommend him on our tour to Siena, Chianti, and San G!
Excellent guide
Miguel our driver and your guide was excellent. Fluent English and Spanish. 10/10. We recommend this tour hands down!
Great driver between towns
Nina_C, Aug 2023
Wonderful guide names Massimo. Very kind, punctual and a great driver. Knowledgeable about the area and gave great recommendations for things to do in Siena and San Gimignano. Great private driver to get between towns. Stopped at Casa Emma winery for lunch - great service, excellent food and great wine. Two guests had nut allergies and the winery was extremely accommodating. Highly recommend Massimo from Chianti drivers for getting around in the Chianti region.
Jamie_R, Aug 2023
Guide picked up our group of 6 from our air bnb in a luxury van. Massimo was a great guide and was full of knowledge of the cities and Chianti areas! We had around 1-2 hours in each city and he ended the tour at Piazzale Michelangelo for stunning views. Would highly recommend this tour!
Misleading title and waste of money
Gopal_M, Aug 2023
The trip is nothing but a driver, somewhat misleading when we were told it is a private tour. The driver doesn’t know much about the towns we were visiting and was reading from trip advisor even though we were told the local driver should be able to describe the towns and the history. On top of that, he was talking about his past customers and described them as “ slobs”. Overall, the Cost of the tour ($720+) is not worth it. I would not recommend it. If it just a a driver, we could get one for half of the money we paid to Viator. It seems, we paid Viator, they took their cut and handed over the trip to Chianti Drivers, and they took their cut and handed us over to a third party independent driver. He was not at all interested in making the trip complaining that he was there only yesterday.,
Roy_G, Aug 2023
Our driver was very knowledgeable and accommodating. Had a lovely lunch in Farm house winery. The Cathedral in Siena is beautiful and a must see.
Simone was a great...
Amy_R, Aug 2023
Simone was a great driver. He was full of information. It was a great excursion. Siena was an unexpected delight and the wine tasting lunch was great.
Perfect day in Tuscany
Stacy_K, Aug 2023
We had a wonderful day trip to Tuscany. Michele was the perfect guide and provided us with a lot of history about the area on our drive. He was very informative and very engaging with our seven year old son. He arranged a lovely lunch at a local vineyard, which was the highlight our trip. The food and wine were delicious. I would highly recommend this tour and Michele!
Brian_C, Jul 2023
Highly recommend! Incredible day - Exactly what we were hoping for and more! Simone made everything fun, seamless, and full of history (which we loved!). The winery was stunning, the food delicious, and wines are not to be forgotten. We are a family of four - with college age children. *we have some food allergies and both Simone and the winery were extremely cognizant and respectful of this.
Perfect day!
Arlyn_C, Jul 2023
Simone was a wonderful guide for our day out with our tween/teen kids! He was warm, engaging and very knowledgeable and informative about the areas we visited. Our tour started promptly on time and he tailored it to our suggestions and at the pace of what we wanted to do and see. I would high recommend this company for your day trip out to Siena/Chianti! One of the best days of our vacation!
Our driver, David, was...
Daryl_I, Jul 2023
Our driver, David, was friendly and knowledgeable. We enjoyed the scenery between towns and not having to worry about train or bus schedules. Great experience for our family
Fantastic Day Had By All!
MrsEA_H, Jul 2023
We had a fantastic day. Enjoyable time spent travelling through the beautiful Tuscan countryside. Our driver David was friendly, knowledgeable and great company. The lunch at the winery was superb!
The Beauty of Tuscany
Phuongthy_N, Jul 2023
Simone and Maximo were our amazing drivers/guides!…My families and I enjoyed their knowledge, spirit and love for Tuscany. The tour offered so much history and majestic views of San Gimignano, Siena and Chianti. Our fantastic guides made our experiences so memorable.
Private Tour of Siena and San Gimiagno with lunch
Alexis_S, Jun 2023
This was an absolutely fabulous outing! Michele was our driver today. Wonderful man and tour guide for the day! He picked us up at our hotel and greeted us with a huge smile. We stopped in sienna first. Along the way he was telling us the history of the area and Sienna itself. We toured sienna on our own taking him up on his suggestions of what to see. Absolutely beautiful town! A must see! We then met back up and headed for the Chianti Region to a small family owned winery for lunch and wine tasting. Magnificent lunch with incredible wines! We learned so much about wines. Food, wine, service and people were amazing. Next stop San Gimiagno. A gorgeous small old Italian town rich with history, shopping, friendly people and yummy gelato! I highly recommend Michele and this tour 100%!
Introduction to Tuscany
Heidi_B, Jun 2023
Fantastic Day in Tuscany. Simone, our tour guide and driver was so amazing and he is the best tour guide !!!
Great day trip out of Florence
Angela_R, Jun 2023
We had such a wonderful day. Our guide suggested we start 30 minutes early to beat the crowds great advice. He was so knowledgeable of the area as he grew up in Siena. He suggested a wonderful small winery which was beautiful and welcoming. We loved Siena and San Giamaggio. Great day. It was a hot day so loved having the car and AC. Definitely book this tour.

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


8 hours
Free Cancellation

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