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
Start time.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
Supplied by
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 433 reviews
Sort by: Most insightful
Kariann_A, Aug 2026
I thought it was pricey since all we basically had was a driver to the three locations. I was expecting him to be flexible go on country road to take pictures of scenery etc. he did not speak good English even though we request English speaking. The two towns were amazing but an hour at each place is
Not enough. The winery was amazing amazing
Thomas_F, Jul 2026
This was an amazing day trip. Our driver Simone was super friendly and knowledgeable and he was flexible with the itinerary. We got to stop at additional places on the way to the main stops for photos and we even went to a winery we have been keen to visit for ages. Would recommend this for couples or small groups.
Response from Host, Jul 2026
thank you so much Thomas!
Heidi_D, Jul 2026
Our trip to Siena was fabulous and Cosimo made the day extra special. He was super knowledgeable and we enjoyed the special day!
Response from Host, Jul 2026
thank you so much
Carmen_A, Jun 2026
daytime trip in comfortable car with an exceptionally attentive guide, Simone. plenty of time to explore Siena and San Gimignano. The lunch in a private winery was certainly the best part of the trip. highly recommended
Response from Host, Jul 2026
thank you dearest!!!
Em_V, Jun 2026
This tour was one of the highlights of our trip to Italy. Sienna and San Gimignano were just beautiful, each with their own unique charm and stunning scenery, giving us a wonderful taste of the region.
Our driver, Marco, was fantastic. He was so relaxed, friendly and great to chat with throughout the day. It was an absolute pleasure to spend the day with him. He went above and beyond to arrange a lunch reservation at a truly magical spot after explaining that the restaurant I had originally requested would reduce our sightseeing time due to its location. His local knowledge and thoughtful recommendations made the entire experience even more special.
The winery for lunch was absolutely incredible—the scenery was straight out of a movie. The setting, the food and wine and the atmosphere exceeded all of our expectations.
This was the perfect way to see some of the region. It was an experience we will always remember. I would highly recommend this tour to anyone visiting Tuscany. Thank you Marco for such a special day!
Response from Host, Jun 2026
We're happy to read your thoughts about us. It's our mission! Marco will appreciate that! Thank you
Karin_H, Jun 2026
This was a great way to get out to the wine country. Our driver was nice and efficient. It was a great tour if you want a private driver to go Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence. If you want a tour guide, pick another tour. We just needed a driver.
Response from Host, Jun 2026
Thank you Karin!!!!
Kyle_B, Jun 2026
Our tour guide was amazing and especially friendly to our kids. I would want Cosimo again if I had the chance
Response from Host, Jun 2026
very cool!!!
thanks
Lauren_R, Jun 2026
Incredible day! This was such a beautiful day with such a knowledgeable tour guide. We were also able to add a stop based on our interests.
Response from Host, Jun 2026
Thank you Lauren!!
Bill_W, May 2026
This was one of the highlights of our Italy trip. The Mercedes Sprinter van was comfortable, and the stops in Siena, San Gimignano, and the Tuscan winery were excellent.
What made the day truly special was our driver, Fabrizio. He was knowledgeable, engaging, and went above and beyond by helping us secure a separate winery reservation. Traveling with our 15, 21, and 23-year-old children, he made the experience fun and memorable for everyone.
The scenery, wine, and hospitality were outstanding. We would highly recommend this trip to anyone visiting Tuscany.
Response from Host, Jun 2026
Fabrizio is super!!! All my drivers are really good!! Very happy about your daily tour feedback
Grace_S, May 2026
Lovely day in Siena and Chianti with Marco. Excellent food and wine. Highly recommend this day trip from Florence.
Response from Host, May 2026
Thank you so much Grace!!
Kerri_J, May 2026
This is our second time booking the same tour- JUST AS GOOD AS THE FIRST TIME !!!! AND- we'd book again the next time we visit.....not many places are worth this level or repeats. Thank you!!!!!
Response from Host, May 2026
Hi Kerri, we're truly honored that you find our service so high-quality! We look forward to seeing you again next time to give you the best.
Kenneth_S, May 2026
Tuscany is beautiful and the tour was a delight. Our driver Fabrizio did a nice job dropping us in all the right spots in Siena and Gmignano and was always right where expected to pick us up. Great stop for lunch at a winery.
Response from Host, May 2026
thank you dearest
Angela_G, May 2026
Carlo was excellent! Great service and helped to make the tour perfect for us! Stopping at some extra spots to make the experience fit what we were interested in. He was filled with knowledge to answer questions yet gave us our own space to explore too! Would definitely recommend! Great wine tasting too!
Response from Host, May 2026
Happy about your review! Thank you dearest and hope to see you again!!
Lori_A, May 2026
This was a wonderful day. Both cities were so unique and beautiful. Our guide, Samuel, was very knowledgeable about the area and made us reservations for lunch and wine tasting at a beautiful winery. I would highly recommend this to my friends.
Response from Host, May 2026
Love your review!!! We are ready to arrange the best we can do. See you soon!
RONALD_w, May 2026
Our driver was fantastic. Took us to a little winery for lunch. Was magnificent! Like out of the movies.
Response from Host, May 2026
Thanks a lot Ronad! Cosimo is a great expert driver. I will share with him your nice review
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.
Response from Host, May 2026
Hi Mrs Lanigan,
I'm sorry for your disappointment, but the service you purchased wasn't for a driver-guide, but simply a tour with an experienced driver at your disposal. By law, we can't accompany you or act as a guide. You probably booked something specific the day before with another company. If you were expecting a guide, we also offer them on the platform under the heading "Private guided tour." Thanks anyway.
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
From $835.21
per group (up to 7)up to 24 hours before the experience starts (local time)
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