Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence
Recommended by 95% of travelers
Florence, Italy
- 8 hours (approx.)
- Pickup offered
- Mobile ticket
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Overview
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 car or minivan
- Bottled water
- Onboard Wi-Fi (on request at reservation)
- Air-conditioned vehicle
- expert english speaking driver
- Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult
- mance
- Licensed Guide in Siena
Meeting and Pickup
Pickup points
Select a pickup point
Pickup details
Pick up from all hotels or apartments in Florence downtown
Operating hours.9:30 am
Itinerary
This private Tuscany day trip provides convenient pickup from anywhere in downtown Florence, making getting started as easy as possible. On the day of your tour, get picked up in a luxury minivan and prepare for a great introduction to the Chianti wine region, Siena, and San Gimignano.
This private trip is tailored for your group alone, providing an intimate exploration of some of the most famed parts of Tuscany.
After pickup, head to Siena, where you visit local landmarks such as the Piazza del Campo, home of the famous Palio, and the Siena Cathedral. Explore the town’s medieval streets, taste local food, and shop for gifts (own expense).
Continue along the famous Chianti Wine Road to the lovely hill town of San Gimignano, where you spend about two hours exploring the historic center before returning to Florence.
If you choose the option with a winery lunch, you’ll stop to taste wines and local food products, but will have less time to explore other destinations on the itinerary.
This private trip is tailored for your group alone, providing an intimate exploration of some of the most famed parts of Tuscany.
After pickup, head to Siena, where you visit local landmarks such as the Piazza del Campo, home of the famous Palio, and the Siena Cathedral. Explore the town’s medieval streets, taste local food, and shop for gifts (own expense).
Continue along the famous Chianti Wine Road to the lovely hill town of San Gimignano, where you spend about two hours exploring the historic center before returning to Florence.
If you choose the option with a winery lunch, you’ll stop to taste wines and local food products, but will have less time to explore other destinations on the itinerary.
1
Siena
2 hours • Admission Ticket Free
2
San Gimignano
2 hours • Admission Ticket Free
Strada Statale 222 Chiantigiana (Pass By)
3
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
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.8
based on 413 reviews
Nat_K, Apr 2026
We had a lovely tour in San Giamanno at the personal home of a local owned winery, Terre Di Sovernaja. The prepared meal and wine tastings were fantastic! We thank them for their generous hospitality. Our private guide, Marco, set up.
Peggy_L, Apr 2026
We definitely did not think this was worth the money. We expected a tour guide on our long hours of driving and we basically had a driver. He was very nice if we asked him questions, but he didn’t really offer much in the way of information. The day before we had had a walking tour with an absolutely delightful young man, and he talked the whole time we walked, and it was such an enjoyable experience. We certainly hoped for this same type of thing when we were driving such a good portion of the day.
Dana_S, Mar 2026
Great experience. Tailored trip
To our needs. Clean and nice vehicle. Great service and kind driver.
Response from Host, Apr 2026
thank you so much
Mike_A, Mar 2026
Fun trip with the family, we especially enjoyed the winery visit with lunch. Our driver and guide was Samuel’s was informative and drove safely
Response from Host, Mar 2026
Much appreciate
thanks
Chris_B, Mar 2026
It’s all about the guide. Marco was the absolute best we could have asked for. He had an extensive knowledge of the area and a great recommendation for a private wine tasting on a family winery/farm. Great day!
Response from Host, Mar 2026
Thank you so much!!!
ian_m, Mar 2026
Great local family owned vineyard experience. Great guide full of local knowledge and experience. Would recommend.
Response from Host, Mar 2026
thank you
w6sx8x2frj, Jan 2026
Tour was perfect from beginning to end. Loved being able to customize on the spot. Do not skip lunch, we did Poggio Amorelli and loved every minute of it!
Response from Host, Feb 2026
Thank you so much
Vincent_A, Dec 2025
Simone is hands down the best tour guide. Super friendly and warm and a wonderful storyteller! He went out of his way to bring us to the best spots for panoramic views, gave us great recommendations for dining in Florence and Rome. The tour that Simone put together is definitely one of the highlights of our very first visit to Italy. Thank you!
Response from Host, Feb 2026
I am falling in love for your fantastic words!!! Very happy, thanks a lot
Kennedy_P, Dec 2025
Massimo was an excellent driver and very kind. The scenery was beautiful and crowds were minimal. Only docking this experience 1 star because the day felt very long, and there wasn't much to do besides walk around with no guide. The winery was not worth the $165 if you're not a red wine drinker.
Response from Host, Feb 2026
Very appreciated!!! all my best
Christopher_G, Nov 2025
The personal touch from the tour was second to none. Our guide Marco was fun, informative, prompt and provided us with a one of a kind luncheon hosted by a working winery family. Amazing!
Response from Host, Feb 2026
Thanks a lot
Dean_S, Nov 2025
This was an incredible experience getting outside of the city and going to the historic towns of Siena, San G, and Chianti. Our private tour guide, Simone has been guiding for 23 years, and was raised in Florence. His knowledge, and hospitality were 5 star! We love to book the private tours as we not only get to learn history, see beautiful towns and cities, but create wonderful memories. We ended up at a vineyard in Chianti and the day turned out perfect! Highly recommend Simone. Genuinely great person and passionate about sharing his knowledge and history of the area.
Response from Host, Feb 2026
1000 thanks
Susan_S, Nov 2025
The tour with Samuele was wonderful and he is so knowledgeable about the Florence and Tuscany areas. He gave us a lot of information and facts about the areas we did not know about. It was a fantastic end to a long trip to Greece and other parts of Italy and it was nice to have the private tour with him in a very comfortable van.. He is a great driver too!
Response from Host, Feb 2026
thank you so much
tasnim_k, Oct 2025
Massimo was absolutely fantastic he went out of his way to shoe us part of Florence that was not included. He never rushed us, we took our time to see San Gimignanomi and Sienna and the wine tour. Definitely recommend Massimo and Viator. So far we have enjoyed all the services provided through Viator Tours. Thank you Massimo for an incredible experience.
Response from Host, Oct 2025
Thank you to you dearest!!!
JeanLouise_D, Oct 2025
My husband and I had an amazing experience with our driver, Marco. He was very flexible and knowledgeable about the history of the area. He supplied us with options and tailored our day around what we wanted to do and see. I highly recommend the lunch in the vineyard with the wine tasting! We had a great day!
Response from Host, Oct 2025
Thank you dear!
Doug_B, Oct 2025
What a great day! Visiting Siena, driving through the beautiful Tuscan countryside, and eating at a winery were the perfect activities after a few days in Florence.
Response from Host, Oct 2025
thank you
Laura_S, Oct 2025
Marco was an amazing driver and so knowable. We had a great time. He took us to a cute winery for a tasting lunch and to two smaller walled cities and sienna.
Response from Host, Oct 2025
Thank you Laura
Paul_S, Sep 2025
We stopped at Montaregioni, Sienna, a beautiful winery in the Tuscan countryside for lunch and wine tasting and finished at San Gimignano. It was a perfect day and a perfect pace. Carlo was very knowledgeable and amenable to all our wishes. Great day.
Response from Host, Oct 2025
Thank you Mr Smith
so kind to send it!!!
Daniel_K, Sep 2025
The driver, Samuela, was very knowledgeable, friendly, courteous, helpful, and took us to an excellent winery tour and lunch. However, Samuela is not a tour guide and could not accompany us and guide us through the sites. We expected a tour guide, not a self-guided tour. Therefore, I think a refund is in order as this tour is completely misrepresented.
Response from Host, Oct 2025
hi Mr Kaufman
in our details tour this is what we usually do:
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.
and more there is expressly described that you will have expert speaking english driver
if you wanted a guided tour you should buy or tour with the licensed guide in loco
all my best
Jennifer_C, Sep 2025
David was great- good insights on the town and very friendly! We loved the lunch at family vineyard in Chianti. Amazing. Perfect way to explore the countryside of San Gimignano and Siena. Highly recommend
Response from Host, Oct 2025
Thank you Jennifer!!! all my best!!
Kevin_M, Sep 2025
Our driver Marco was fantastic. He was engaging and knowledgeable, having been born and raised in Siena. The vineyard we stopped at for lunch was a great family run winery. We got to meet the owner and had a knowledgeable guide give us a tour there. The view during lunch of the hills and valley around the vineyard was stunning. Marco offered an option to replace our visit to San Gimignano with stops at two small villages with a scenic drive through the mountains. We found this a nice chill alternative and authentic Italian experience after walking among so many tourists in Siena and Florence. We would do this tour again in a heartbeat.
Response from Host, Oct 2025
So glad about it!!
James_B, Sep 2025
This was our favorite highlight of the trip. We have traveled quite a lot and can hands down say Marco is the best guide anyone could have. We learned a lot of interesting facts about his country. The winery lunch and visit was so relaxing and enjoyable. Wonderful day all the way around
Response from Host, Oct 2025
Thank you dearest!
Laura_S, Sep 2025
Our driver and guide Marco spoke excellent English and was from Siena originally so he had lots of local knowledge of both Siena and San Gimignano where we went. He was flexible, clear and very pleasant. Would highly recommend him and this tour.
Scott_P, Sep 2025
Our trip was amazing! I would recommend a a private tour with David he was very personable and timely. He recommended an amazing winery that gave us a true taste of the Tuscany culture. He spoke great English so Conversation flowed throughout the day. Chao David hope to see you in Texas soon!!!
Response from Host, Sep 2025
Hi Scott
thank you so much...I will share it with David!
Valerie_B, Sep 2025
Our driver,Sergio, was prompt, polite, and informative. He picked us up at our hotel and took us close to the entrance at every stop. The tour did not include tickets to the cathedral or the cost of lunch. The lunch was delicious! We had plenty of time to enjoy the beautiful scenery of Tuscany. Sienna is a gem!
Response from Host, Sep 2025
Thank you Valerie!!!!
Dwight_S, Sep 2025
First class excursion starting being picked up at our hotel in a beautiful Mercedes sedan along with excellent driver/tour guide Marco. He listened to our individual lunch desires, which we appreciated. Perfect amount of leisure time including lunch in Sienna. Excellent all around. Highly recommend.
Response from Host, Sep 2025
Much appreciated Mr Dwight! Hope to meet you again!!
James_C, Sep 2025
Cosimo was a great driver and host. We enjoyed Siena, SG and especially lunch at Casa Emma. Cosimo helped us plan the day and answered all our questions along the way.
Response from Host, Sep 2025
Thank you so much
Judith_R, Aug 2025
Waste of money. Way too expensive for what it provided. A driver picked us up at our hotel and drove us to the towns. We were left to wander around and then he meet us at an arranged time to drive us elsewhere. He provided some commentary on the way. I would not call this a private tour. It was a private driver. Had I known I would have arranged guides in the towns and either taken the train or driven myself. Absolutely not worth the exorbitant cost
Response from Host, Sep 2025
Dear Sirs, my driver remembers you very well. You were kind and pleasant. However, I'd like to emphasize that your complaint is mainly about my driver leaving you in Siena and San Gimignano without accompanying you. We are not licensed guides. If you wanted this, you should have purchased the Siena tour with a guide. My driver told you about the Palio and other news while driving, but he couldn't have gotten out and left the vehicle to go with you on a tour of the cities. Next time, you'll know what you need and purchase the tour you're waiting for.
All my best
Josh_M, Aug 2025
This was a great day trip. We were traveling with our daughters and wanted to show them more than just the big cities, so Simone took us outside of Florence. I was very interested in getting to Sienna because they were preparing for the horse race the following weekend. They loved it. We didn't do the winery lunch so we could spend a bit more time in town where we enjoyed an amazing meal. Great experience for everyone and Simone's conversations / history and vehicle was a pleasure during the drive.
Response from Host, Sep 2025
thank you
Vicki_C, Aug 2025
Amazing day touring beautiful Tuscan region with Simon. He was always helpful with ideas for options. Highly recommended.
Response from Host, Sep 2025
thank you
Terri_L, 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.
Response from Host, Sep 2025
Thank you very much for your words Terri
I will share about with my driver Samuele
thanks again
From $823.12
per group (up to 7)up to 24 hours before the experience starts (local time)
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Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence
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