PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence
Recommended by 100% of travelers
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Florence, Italy
- 8 to 9 hours (approx.)
- Pickup offered
- Group discounts
- Mobile ticket
- Offered in: English
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Overview
Get out of Florence for the day to see Tuscany highlights on a private tour to Siena, San Gimignano, and Monteriggioni. Door-to-door transport and all logistics are arranged, so you can focus on sights like Siena’s Piazza del Campo and the UNESCO-listed medieval towers in San Gimignano. Complete the experience with an optional private lunch at a hand-picked Chianti farm or winery.
- Explore the Tuscan countryside without the hassle of renting a car
- Learn the history behind three charming medieval towns
- Travel comfortably in an air-conditioned minivan with room for 6
- Private transportation with an English-speaking licensed driver
Sample Menu
Starter
• Starter
Bruschetta with spicy Arrabbiata sauce, Bruschetta with fresh tomatoes and basil, Bruschetta with extra virgin olive oil
Starter
• Starter
Tomato salad with mozzarella and 8 years old balsamic vinegar
Main
• First Course
Spelt salad with chickpeas and mix vegetables dressed with 8 years old balsamic vinegar.
Main
• First Course
Ricotta cheese with 30 years old balsamic vinegar.
Main
• First Course
Cheese and Prosciutto
Main
• Second Course
Scrambled eggs with truffles.
Main
• Second Course
Arista (pork loin cooked in the oven)
Main
• Third Course
Lasagna with wild boar and pork (“Cinta senese” free range) meat sauce (also available vegetarian, or vegan, or Gluten free)
Dessert
• Dessert
Gelato dressed with 30 years old balsamic vinegar
What's Included
- Pick-up and drop-off at your selected hotel/location (in Downtown Florence)
- Private transportation by MiniVan, Air-Conditioned
- English-speaking licensed driver
- Free time in Siena and San Gimignano
- Unlimited cold mineral water
- On-Board WiFi
Meeting and Pickup
Pickup points
Select a pickup point
Pickup details
You will be picked up directly at your hotel or address (in Florence Down Town) communicated at the time of booking at the start time of the tour. Upon request, you can change your pickup time (24hours before) We do not pick-up at train stations or airports.
Itinerary
1
Siena
2 hours • Admission Ticket Free
Duomo di Siena (Pass By)
Piazza del Campo (Pass By)
2
Monteriggioni
1 hour 30 minutes • Admission Ticket Free
3
Marronaia Wine Garden
2 hours • Admission Ticket Not Included
4
San Gimignano
1 hour 30 minutes • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Stroller accessible
- Near public transportation
- Infant seats available
- Most travelers can participate
- In case of rain the umbrellas are provided by your driver.
- Kindly share your mobile number for an easy communication during the pickup
- This tour/experience will have a maximum of 6 travelers (your private party).
- With agreements during the reservation we can organize lunch in winery, this is a highly recommended experience, especially for the wine lover. Dedicated lunches for people with cilia, allergies or vegetarians. (This option will exclude the possibility to visit the fortress of Monteriggioni). **Lunch in winery available (as an option on request) at an extra cost 55€pp to 65€pp per person. **
- Departure is suggest at 9:00am. Pick-up time can be choise during the reservation
- Authorized guide not included
- Minors under 18 years old are not allowed to drink alcohol (wine tasting)
- 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
5.0
based on 250 reviews
Chris_C, Apr 2026
Alessandro did a wonderful job with this tour. We got out into the Tuscan countryside and he was a wealth of knowledge about the history of Florence and the entire area. We got to see Siena and San Gimignano which are 2 completely different experiences. The wine tasting and lunch was a great addition. I would highly recommend this tour if you have never spent anytime here. The area is beautiful and so rich in history.
Jeanne_S, Mar 2026
Alessandro is an amazing guide. Friendly, knowledgable and an excellent driver. The Tuscan countryside enroute to Siena was stunning. Rolling hills, olive trees and vineyards. Our first stop after leaving Florence was Siena. Siena cathedral is a stunning example of Gothic architecture. Built primarily in the 12th and 13th centuries, the cathedral is laden with black-and-white marble façade. Interior sculptures and paintings are everywhere. After a refreshing affogato, we headed to San Gimignano first stopping for lunch and wine tasting at Tenuta Guardastelle. Nothing short of spectacular and picturesque with amazing wines. Next stop was inside the walls of San Gimignano, a perfect example of a Tuscan medieval city. Lots of shopping for salami’s, pecorino, leather and of course gelato. A fantastic tour for sure all thanks to Alessandro. Gratzie!
Carmen_F, Nov 2025
A wonderful experience! We went for our honeymoon and this was truly a sweet relaxed day! Completely customed to what we would like to do with the day and our guide was so knowledgeable.
Judy_L, Oct 2025
We loved our trip with Alesondros. He was very knowledgeable about the area. We had a lovely lunch inside a medevil village.He was also punctual in picking us up.
Zalma_S, Oct 2025
I cannot recommend this enough! My husband and I booked this for our honeymoon and it was such a great experience!! It was so wonderful to get to know the Tuscany countryside and Alessandro was just the greatest guide ever, he explaines everything to perfection and gives you free time to explore on your own. We will always remember this experience, it was one of the best days of our honeymoon. Please do not hesitate to book the optional wine tasting it was a once in a lifetime experience and everything was delicious!!!
Adria_B, Jul 2025
This tour was a highlight of our trip. Alessandro was fantastic - very friendly and knowledgable. We had enough time to explore each location. We also chose the option of having lunch at a winery and loved it - we are still talking about that meal. We would definitely book another tour with Alessandro again, and we have already recommended this tour to other folks. Thank you!
nk6ktbrg68, Apr 2025
Alessandro took us to all the sites with friendliness and ease. Super convenient service and overall wonderful experience. Be sure to include the lunch and wine tasting!
Martin_B, Oct 2024
Allesandro was fantastic with his knowledge of wine and the area. Plenty of time was given at each stop and the lunch/wine tasting was incredible.
Connie_B, Sep 2024
We had an incredible experience touring the Tuscan countryside with our fantastic driver, Alessandro!
From the moment he picked us up—right on time—to the end of the day, everything detail was considered. He was enthusiastic and knowledgeable and made the entire tour so much fun. He even had a supply of cold water in the van, a lifesaver on a hot September day in Italy.
What we loved most was the perfect balance of structure and free time. Our driver allowed us plenty of opportunities to explore the beautiful Tuscan cities, giving us time to shop, eat, and take plenty of photos at our own pace. There was never any waiting around, which made the day feel seamless and relaxed.
If you're looking for a memorable way to experience Tuscany, this tour is the way to go. Highly recommended.
Gina_L, Sep 2024
We had an absolute fabulous time with Alessandro. He was very knowledgeable about tuscany, italy and wines which we loved and took with us back home. He made the ride smooth and enjoyable. Thank you so much for making the experience great!!
Sylviacole, Aug 2024
From the moment that Alessandro picked us up at our hotel we knew we were in for an amazing day. I was traveling with my husband and in-laws. Alessandro gave us great insight and information about each location while on the drive. We chose to have lunch in the town of Monteriggioni after taking some time to walk along the wall. I can't recommend this tour and Alessandro enough, don't hesitate to book. While it is a full day, it never felt rushed and we were able to visit and enjoy time in Sienna and San Gimignano. This day was definitely the highlight of our trip to Italy. There's so many options and tours to consider, but I can truly say that this tour will provide a perfect day in Italy!
Michael_c, Jul 2024
Saw the two mountain towns and casa Emma winery - plus countryside as we drove
Guide very accommodating to shopping delays and picture stops
Very informative on the drives
Broke drive up so not in van too long
Did NOT guide in the cities - basically dropped us off and gave us pick up spot - do do your own research in each city to figure what you want to see
Response from Host, Mar 2026
Ciao Michael,
Thank you so much for sharing your experience! I’m really glad you enjoyed the Tuscan villages, the visit to Casa Emma, and the beautiful countryside views along the way. It’s great to hear that you appreciated the flexibility for photo stops and shopping—my goal is always to make the day as relaxing and personalized as possible for you!
I’d just like to clarify one small detail regarding the city visits for future travelers. As mentioned in the tour description, the service I provide is as a private driver-guide: by law, I can provide all the historical information and stories during the drive, but I am not permitted to act as a walking guide inside the city centers or monuments.
The best part of my private tours is the total flexibility: since it’s a dedicated service just for you, if you had let me know you'd like a licensed walking guide for the cities, I could have easily organized one to join us!
I hope your memories of Tuscany stay with you for a long time, and I look forward to seeing you again for another adventure together.
Warm regards,
Alessandro
Michael_D, Jul 2024
Alessandro was an amazing host. Picked us up right from the door of our stay and captivated our group of four en route to Siena. He gave us a wonderful overview of the area, the wine context, and engaged us like family. At Siena and San Gimignano, we were oriented to each city and we roamed for a couple of hours and then rendezvous at an easy to find location. Lunch and wine tasting at Podere La Marronaia was exquisite. Like having your college best friend from Tuscany proudly showing off his home country. I will recommend Alessandro to all of my friends considering a visit to Florence.
Raana_Z, Jul 2024
We had an amazing day in Tuscany with Alessandro as our driver. He was very friendly, enthusiastic, knowledgeable, and professional. Our day was planned perfectly with enough time in each stop. The vehicle was very comfortable and could easily fit more than our family of four. I highly recommend Alessandro!
Sachin_T, Jun 2024
Alessandro is outstanding. His drives safely and corteously, while educating us thoroughly about the towns and countryside of Tuscany. We learned much about he wine and food culture, as well.as the history of the area. His enthusiasm is contagious! Lunch at Ristorante da Remo (in Monteriggio) was delicious. Siena is a must, especially the Gothic details of the Cathedral.
Tom_W, Jun 2024
Alessandro was beyond expectation: Fun, courteous, informative, punctual, graciously flexible, quality of service and recommendations for activities and dining.
Kate_M, May 2024
I CANNOT RECOMMEND THIS TOUR ENOUGH!!! Alessandro is an absolute pro, and made this experience one of the highlights of my honeymoon. Any person that ever tells me they are visiting Tuscany/Florence from here on out, I will INSIST they spend a day taking a tour through UNIQUE TUSCANY. 1. Every tour is customizable, so while Alessandro will make wonderful suggestions, he is great about making sure he can accommodate specific requests. 2. I cannot get over his vast breadth of knowledge, and how generously he shares it. We learned so much about each sight we visited, interesting facts about everything we drove past, history about Florence + Tuscany, about how different wine and olive oil producers make their products - there was nothing we asked about that he didn't have thorough answers to. 3. His passion and love for Florence and Tuscany is infectious. 4. He made wonderful recommendations for every category of activity we were interested in. 5. He makes the entire day seamless, as you are dropped off and picked up at the most convenient spots. He made it so that you never had to double back anywhere to meet back up with him - you can truly make the most of your time in each location you visit. I urge you to book through this company. You will be SO grateful you did. THANK YOU, ALESSANDRO!!!
Michael_J, May 2024
Allesandro was a terrific guide with excellent knowledge of the area surrounding Florence. He gave us plenty of free time and flexibility to explore Siena and San Gimignano on our own and made several stops for photo ops as we drove through the Tuscan countryside. Can't say enough good things about this experience. Highly recommend this tour.
Julie_S, Mar 2024
Great tour of the countryside with recommendations for gelato and stops for pictures. Allesandro was a pleasure.
Kristi_B, Nov 2023
We had a great day which included a wonderful lunch and wine tasting. Alessandro was a fabulous guide and driver. We enjoyed walking around San Gimignano and Sienna at our own pace. And being picked up and returned to our hotel was an added bonus. Would definitely recommend this day trip>
Diane_A, Sep 2023
Alessandro was so knowledgeable and friendly, our lunch visit to the winery was outstanding.
Overall, a lovely day with dear friends in one of the most beautiful places in the world!
schmawn, Aug 2023
Our day with Alessandro was super convenient and a pure delight, despite the cold/wet weather (and food poisoning I had gotten in Venice the day prior which might have made the winery lunch/tasting a challenge if not for how fresh and simply delicious the food was). The pic reflects the weather in Siena (which was still remarkable and worth every minute!). Alessandro is local to Florence and generously shared insights which were invaluable. He is professional, reliable, and a joy to spend time with. We are already scheming about how we might engage him for another Tuscan adventure knowing we can trust his impeccable good taste and excellent service. Highly recommend!
John_B, May 2023
We had a wonderful day exploring Tuscany. Lunch was at a picturesque winery overlooking a valley and San Gimignano. Our driver, Alex, went out of his way to ensure every detail was perfect. Thoroughly enjoyed trip.
Barbara_R, Oct 2022
Alex was so much more than a driver. He gave us lots of information about the areas we were to see and was extremely helpful. Really enjoyed the countryside. Thought both Sienna and San Gimignano were beautiful. Would definitely do this type of trip again in other locations.
HughWeily, Sep 2022
Seeing both Sienna San gimignano.
Lunch at Montereggiano…..All wonderful!!
Our driver was so helpful and anxious to answer all our questions. It is truely one of the highlights of our trip. It’s hard to see how this experience could have been any better.
Donna_G, Sep 2022
Alessandro was an excellent guide. He was pleasant, enthusiastic and accommodating to our group. We highly recommend him and this tour!
Anthony_D, Jul 2022
Great tour of Sienna and San Gimignano. These two towns are visually spectacular. The drive through the countryside of Tuscany is beautiful. Our guide Alessandro was great and recommended a terrific restaurant for lunch in the small town of Monteriggioni.
Amanda_M, May 2022
The perfect combination of stops, lunch, and a beautiful drive. I recommend taking this tour to see the amazing country side and small towns of Tuscany. Our driver, Alex, was so accommodating and informative. He made the trip incredible !
sbarnett, May 2022
Alessandro was a wonderful tour guide. We all Enjoyed Siena and especially the tour of winery. The scenery was spectacular. A great introduction to this region of italy
Adrianna_S, Apr 2022
Alessandro was an amazing tour guide. This was hands down our best part of our 2 week Italy honeymoon. He took us all over Tuscany, was extremely pleasant, gave us many recommendations for food, and called to reserve the most amazing wine tasting and lunch at Podore La Marranoia in San Gimignano. Book this tour with Alessandro!
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