Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region
Recommended by 91% of travelers
Badge of Excellence
Florence, Italy
- 8 hours (approx.)
- Pickup offered
- Group discounts
- Mobile ticket
- Offered in: English
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Overview
Venture to the notable wine regions of Tuscany on this private day trip from Florence. Enjoy the scenic drive through the Tuscan countryside and hop out to capture photos along the way. Venture into Siena and San Gimignano to explore must-see medieval landmarks at your own pace and finish your experience in Chianti with an optional wine tasting at a local winery.
- See the best of Tuscany on this full-day trip from Florence
- Forgo generic group tours for a private and personalized excursion
- Travel comfortably from your hotel in an air-conditioned vehicle with WiFi
- Opt for a winery experience along the Strada Statale 222 Chiantigiana wine route
What's Included
- Door to Door Hotel pickup and drop-off
- Expert Professional Driver at your full disposal
- Independent Sightseeing in Siena, San Gimignano and Chianti Wine Region
- Wine Tasting Experience in a quaint Chianti Winery - if option selected1
- Direct access to the historic centre of UNESCO Listed Art Cities
- Tailor made Itinerary
- Commentary on board
- Photo Stops along the Way to portray the most beautiful landscapes of Tuscany
- Dedicated office support available before, during, and after the tour to customize the experience
- Air conditioning and USB charger on board
- Fully-fitted Mercedes vehicle with Free Wifi on board
- Lunch
- Local guides in San Gimignano and Monteriggioni
Meeting and Pickup
Pickup points
Select a pickup point
Pickup details
Your private driver will pick you up directly at your hotel or apartment's lobby
Itinerary
Depart Florence in the morning with pickup from your centrally located hotel, and then settle in the comfort of your private vehicle during the drive to Tuscany.
On arrival in Siena, spend some free time wandering the city's historical center. See the Piazza del Campo and the Italian Gothic cathedral at the Palazzo Pubblico.
Leaving Siena behind for San Gimignano, you'll notice the pretty town's 13 towers from a distance. Relax as you amble past the weathered stone buildings and discover the town's hidden gems—it's an ideal place to purchase a meal accompanied by a glass of wine (own expense).
Then set off for Chianti for more free time. If you choose, you can your a local winery and get a sense of traditional Tuscan life (own expense), and learn how wine is processed and produced.
Afterward, you're dropped off at your hotel in Florence.
On arrival in Siena, spend some free time wandering the city's historical center. See the Piazza del Campo and the Italian Gothic cathedral at the Palazzo Pubblico.
Leaving Siena behind for San Gimignano, you'll notice the pretty town's 13 towers from a distance. Relax as you amble past the weathered stone buildings and discover the town's hidden gems—it's an ideal place to purchase a meal accompanied by a glass of wine (own expense).
Then set off for Chianti for more free time. If you choose, you can your a local winery and get a sense of traditional Tuscan life (own expense), and learn how wine is processed and produced.
Afterward, you're dropped off at your hotel in Florence.
1
Florence
1 hour • Admission Ticket Free
2
Siena
2 hours • Admission Ticket Free
3
Piazza del Campo
30 minutes • Admission Ticket Free
4
Duomo di Siena
15 minutes • Admission Ticket Free
5
San Gimignano
1 hour • Admission Ticket Free
6
Piazza Della Cisterna
30 minutes • Admission Ticket Free
7
Strada Statale 222 Chiantigiana
15 minutes • Admission Ticket Free
8
Strada Statale 222 Chiantigiana
15 minutes • Admission Ticket Not Included
9
Florence
1 hour • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Please advise any specific dietary requirements at time of booking
- A maximum of 8 people per booking
- Stroller accessible
- Service animals allowed
- Near public transportation
- Infants must sit on laps
- Infant seats available
- No heart problems or other serious medical conditions
- 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
4.7
based on 134 reviews
Chris_P, Apr 2026
We were on a 2-1/2 week vacation and this was by far one of the best experiences we had. The countrysides are beautiful and mostly breathtaking. Our drive (Valetine) was awesome - friendly, knowledgeable and informative. The cities we visited (Siena and San Gimignano), as well as the ChiantiWinery were all fantastic! I would definitely recommend this tour!
RENATA_P, Apr 2026
Was absolutely stunning
Milko was our driver . Such a lovely person
We enjoy all the ride with him
I surely recommended to do this tour
Carol_D, Mar 2026
Wonderful tour, so much to see. Valentin is an excellent tour guide who took us to these beautiful places, gave us the history and allowed us enough time to see each. This was such a fun day and a must do when in the area.
Sarah_H, Mar 2026
Valentin was a great on our day trip to discover Tuscany! He quickly swung by one of the American cemeteries from WWII. It was closed but he wanted us to know that it was here. We continued on our tour and he gave great suggestions for us to check out at each stop.
Trent_K, Nov 2025
Placido was a fabulous host and we thoroughly enjoyed our private tour. Lunch at the farmhouse/artisan winery was brilliant.
James_V, Nov 2025
Our driver Placido was wonderful. He was well versed in Tuscan history. Our tour was individualized for us, and not rushed. We were able to see everything we wanted. Placido was the perfect guide for this tour, we will definitely be requesting him again.
Larry_M, Oct 2025
We cannot say enough praise for this tour adventure! Our guide Placido—he was phenomenal! He goes above and beyond, knows all of the best places to go and he set up a wine tasting and lunch that was spectacular!! We highly recommend this tour!
The sights in Tuscany were breathtaking, , the special access he has in the cities was a significant advantage over other tours and our guide paid attention to every detail . This day was the best way to experience Tuscany!
Julie_L, Oct 2025
Our guide Valentine was amazing!! He was very knowledgeable and took great care of us!! We enjoyed all of our stops! The lunch was amazing in Siena! The winery in Chianti region was so good!! San Gimignano was so cute!! Great gelato @ shopping!!
charmaine_L, Oct 2025
We had a very experienced driver and he was nice. A little challenging to communicate with and understand. We really enjoyed our day however we felt it was pretty rushed and would have liked to spent more time at our stops. Since we were going from Florence to Panzano next time, we will probably go a different route and save a little money and have more time.
Sheila_G, Oct 2025
This was a very full day. I added extra time to this tour to ensure that we were not rushed. But even still, we needed more time to fully enjoy Sam Gimignano. One more hour would have been perfect. San Gimignano is so quaint. You just want to have time to learn about it and enjoy it, not just an hour to go through the streets. Our lunch was at a wonderful vineyard that I had pre-selected. And we ended with Siena, which was very nice as well. Our Tour Guide’s in San. Gimignano (Sara) and in Siena (Laura) were wonderful. I highly recommend adding the guided tour option to this tour as well. Overall, we added an extra hour plus the guided tours and lunch at a vineyard. It was definitely worth the experience.
As a bonus, at the end of our tour, our driver (Christian) took us to a leather factory for a quick demonstration of how products are made. This was a fun side trip on our way back to Florence.
Garett_T, Sep 2025
Placaido is 100% a great guide. Extremely knowledgeable of the area. Even on a rainy day he adjusted our schedule to be more in the car and offer umbrellas when the route could not accommodate a vehicle. The small winery we went to for lunch was terrific. The wine was amazing and the sommelier was very knowledgeable and willing to teach.
Highly, highly recommend Placaido as your driver and guide for this day of your trip.
Twyla_H, Aug 2025
Excellent. Placido made our rainy day a success. We appreciated his attention. While we saw other tours soaked by rain and sheltering, Placido made sure that we were comfortable and continued our tour as the professional that he is. Realizing our culture he took us to the WWII Cemetary/Memorial outside of Florence. We didn't even realize it existed. Placido went above and beyond, we're very pleased that he was our guide.
Adam_S, Jul 2025
Our experience with Christian was five star. He gave us some structure in our private tour yet offered advice based on our love of wine and history. He located a local family owned winery where we enjoyed a wonderful meal in a Tuscan farmhouse, enjoyed beautiful Chianti wine, and toward the medieval cities in the region. It was an epic day and would recommend this to anyone traveling to Florence looking to cover a lot of ground in one day. Christian was hospitable, educational, funny, proud, and knew how to show our family a perfect day. This tour is something that we will talk about for many years.
Siennah_G, Oct 2024
Placido was a great guide. He was nice, knowledgeable, prompt and dropped us very close to each site. He took us to a secluded winery that had great wine and lunch with a beautiful view.
Response from Host, Nov 2024
We're glad Placido was a great guide and that you enjoyed his knowledge and promptness. It’s wonderful to hear you had a lovely time at the secluded winery with great wine, lunch, and a beautiful view!
Best Regards,
CiaoFlorence
Customer Care
Charmaine_G, Sep 2024
We had the most amazing time in Tuscany touring with Placido! From the moment we got into the (brand new) car, he taught us so much about the history, culture and geography of the region and towns we visited. He asked us about our preferences for the day and then planned some very special stops, always asking our permission beforehand. He took us to the most incredible winery for lunch and wine and olive oil tastings. He gave us great recommendations before dropping us in Siena and San Gimignano for us to explore on our own. It was a great break to get out of the city for a day, and Placido was the perfect host. He was professional, charming, and incredibly knowledgeable!
Alysha_P, Apr 2024
We had a great time with our driver Placido! He listened to what we wanted to do and see and made it all happen. He was kind, knowledgeable and took great care of us. He even threw in a few extra gems for us he thought we’d enjoy seeing. Boy was he spot on!!! Took us to the perfect vineyard. Can’t wait to book with Placido again on our next visit to Tuscany.
Tara_B, Mar 2024
We had the best day with our driver Placido! We booked a private tour for 2 adults and 2 kids (11&13), and everyone loved it. We went to Siena, San Gimignano, a few other stops and finished off at the Corbucci winery for a tasting meal that was unbelievable. Highly recommend this tour to anyone wanting a unique tour of Tuscany.
Bette_F, Jun 2023
Placido was warm and wonderful from the first moment we met. He is very knowledgeable and catered our tour to what we wanted to experience. It was a lovely day visiting ancient cities and churches, as well as wineries for lunch and tastings. Really, a perfect day, I highly recommend this tour and our wonderful guide Placido.
Karen_R, Oct 2022
Our driver was very nice, knowledgeable and professional. He gave us great information and was courteous.
Scottie_H, Jul 2022
I would highly recommend this tour. It was the highlight of our trip, and exactly what we needed to relax. Cristian was our tour guide and driver, and he was fantastic. He made the experience enjoyable and informative. We were able to customize our trip and not have to be stuck with a big crowd on a bus. Even the day before we were able to add on a second wine tour, and the travel team was very easy and quick to respond. If you looking for a personable experience this is for you!
Sreedevi_P, Jun 2022
Wonderful guide and friend. He was the most charming gentleman who made us so comfortable. Would really recommend him.
Howard_S, Jun 2022
Driver was great - lunch and wine tasting at La Marronaia spoilt the day for us. Attitude of staff and quality of food was not up to standard. To their credit they did not charge after we complained about service.
Tour556973, Jun 2019
Our tour guide Christian was very knowledgeable about the sites & the wine! The private tour allowed us to customize our schedule. Would highly recommend spending a little extra $$ for this type of tour.
Monica_M, Jun 2018
We have taken many fabulous private tours in Italy but this was our favorite. Julian, our driver was full of history and knowledge. Siena and San Gimignano were wonderful but the real highlight of our trip was the visit the St Agnes Tuscany Winery which Julian arranged. Some of the best food and wine of the trip and we learned much about wine tasting.
Teresa L, Jun 2017
The pros: Tuscany is beautiful and the weather was amazing. The van was clean and we felt safe throughout the entire tour. We were traveling with my older father who uses a walker, and our driver was very accommodating in helping us load/unload and to drive him to the tops of hills/etc to limit walking. The short walking tour in Siena was great and we learned the most during this short walking tour which was led by someone in affiliation with our booked Viator tour. She was fantastic!!!
The cons: There is a lot of ground to cover on this tour. Probably too much, especially when your driver takes you to two wineries without us asking to do so versus the published one expectation. I know... it sounds like we shouldn't be complaining - right? But, we rushed from place to place and were disappointed that we had such little time in Monteriggioni and San Gimignano. After returning home that evening, we re-read the tour description and learned why we were so rushed throughout the day - our driver had added a stop at an additional winery earlier in the day. When we arrived at this winery, we had no idea that is wasn't the one that was included in our package. He didn't tell us. The package says that a wine tour, tasting, and light food would be included in our winery stop. We assumed this was it. It wasn't. We certainly had sticker shock when we received our wine tasting and lunch bill that was 200e. We knew that lunch was not included in this tour, but we were ushered into this winery and assumed it was our included snack and tasting. We didn't order any food, it was simply brought out to us. Our stops in Monteriggioni and San Gimignano included 30-45 minutes of free time at each place. That's not even enough time to walk through the squares/etc. Very rushed. When we asked to just stay at San Gimignano for more time, we were told that we had already paid for the winery stop on the way home. So... this winery stop was the one we paid for. It did include the wine tasting and light food. We purposely picked this tour and it wasn't cheap so that we could see the area and enjoy the towns. If we wanted a multiple winery tour, we would have booked that. We spent about 3 hours total within Monteriggioni, Siena, and San Gimignano and the rest of the day was driving fast and rushed or spent at wineries. Minimal discussion about what we were seeing and the historical significance as we went from place to place.
This was my parents first and most likely only trip to Tuscany so we were disappointed at the rushed experience throughout the day.
Gina_L, Mar 2017
Wonderful tour, our driver Placido was great and gave us so much info along the way. We loved Sienna and San Gimignano. The wine tasting was so much fun!
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