Tuscany Private Tour: Chianti, Siena & San Gimignano

Embark on a private full-day tour from Florence to Siena, San Gimignano, and Chianti. Explore medieval cities, taste Chianti Classico wine, and indulge in traditional Tuscan cuisine.

Duration: 9 hours
Cancellation: 24 hours
Highlights
  • Siena - Siena is a highly popular and frequently visited destination in Tuscany, celebrated across Italy for its remarkable medieval architecture. Upon arrival, delve into its rich history and art by visiting its notable landmarks, such as the renowned seashell-shaped Piazza del Campo and the magnificent Siena Cathedral. The historic streets of…
What's Included
  • Unlimited cold mineral water
  • English-speaking licensed driver
  • On-Board WiFi
  • Private transportation by Mercedes-Benz MiniVan, Air-Conditioned
  • Free time in Siena and San Gimignano
  • Pick-up and drop-off at your selected hotel/location (in Downtown Florence)
Additional Information

• EXCLUSIVE EXPERIENCE FOR YOUR GROUP •
Embark on an enchanting journey to a distinctive part of Tuscany with a private day-trip from Florence. Accompanied by a knowledgeable local driver/guide, delve into the celebrated Chianti wine region and visit the charming cities of Siena and San Gimignano. Explore historic sites such as Siena’s Piazza del…

Location
Siena
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(208 Ratings)
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Anahil982
May 12, 2025
Unforgettable Tuscany Tour with a Fantastic Local Host - We had an amazing private tour through Tuscany!!! He picked us up at the hotel and drove us to San Gimignano, Siena and the Chianti region. He also recommended us to take lunch at Monteriggioni, where we ate the most delicious "pici cacio e pepe". He gave us the freedom to explore each place at our own pace. He was very flexible, allowing us to take more time when ever we wanted. Throughout the day, we had great conversations with Alessandro; he was super friendly, thoughtful, and shared so much interesting information about Tuscany, the food and the wine culture. He also gave us excellent recommendations for the rest of our trip in Florence. We highly recommend this experience with Alessandro, especially if you’re looking for a relaxed and personalized way to enjoy the beauty of Tuscany!
Review provided by Tripadvisor
Hemanf2025
May 2, 2025
TOUR for the three lands in the Toscana . - Hi everyone , if you are looking for a tourist driver , here is the company you need , today we have a fantastic experience with our Driver Alessandro , our pick up was wonderful at Firenze train Station , this man is a one of a kind , so knowledgeable of the Country and its beautiful history, culture , very experienced in driving skills , and so kind to give us time in every city of our tour for taking pictures in the most beautiful places , food , drinks , he provided us with water from his own that we really appreciated , we were very impressed with his kindness and his friendship , it was our first Time visiting ITALY but he make us feel valued, welcomed as a family , after our tour finished he returned us to our Hotel and recommended to us the best restaurants in Fierenze , I HEMAN FERRALES with my wife truly recommend this Man with all his Services , please get in touch with him , please book with him a tour and you will be safe welcomed with no regrets
Review provided by Tripadvisor
David
Apr 30, 2025
Great Day in Tuscany - We had a wonderful time on our day tour through the Tuscany region. We visited the cities of Siena and San Gimignano as well as had lunch and wine tasting at the Marronaia Winery. The whole day was planned out very well for us and Alessandro was a great tour guide. He was very informative and made it a fun day for us all. I would highly recommend this experience
Review provided by Tripadvisor
598chuckf
Apr 28, 2025
Remarkable Italy client experience - Alessandro was one of the most knowledgeable and well spoken guides we have had the pleasure of working with. He creates a client experience that is a blend of empathy, thoughtfulness and anticipation of our needs. When we return to Italy, Alessandro will be our trusted guide.
Review provided by Tripadvisor
Smah12168
Apr 24, 2025
Wonderful day!!! - If you are on the fence about booking this trip with Alessandro let this be your sign to do it. My husband and I did this trip 2 years ago with a larger tour company on a (small) bus and came back this year with our adult children and booked with Allesandro. It is such a better experience this time!!! Really can’t even compare the two—- worth every euro. He is a great guy. So full of great information on the ride… friendly. And the door to door service cannot be beat. Highly recommend!!!!
Review provided by Tripadvisor
Nk6ktbrg68
Apr 19, 2025
Fantastic experience - 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!
Review provided by Viator
Thesue227
Apr 15, 2025
Perfect day trip from Florence - We cannot recommend this excursion enough! Alessandro was friendly, flexible, and knowledgeable, and made sure that we had the opportunity to explore our destinations and enjoy a delicious lunch in a leisurely manner. Don’t hesitate to book a trip with Alessandro!
Review provided by Tripadvisor
294kristenl
Apr 11, 2025
Perfect Day in Tuscany - Alessandro was fantastic. Safe driving, courteous, and so informative. We stopped in Siena, had lunch/wine tasting at Podere la Marronaia, and then a final stop in San Gimignano. It was a fabulous day!!!
Review provided by Tripadvisor
882tamis
Apr 3, 2025
Wonderful day trip in Tuscany - We booked a day tip to Tuscany with Alessandro and it was wonderful. Alessandro picked us up from our hotel in Florence and we drove to Siena. His van was super clean and comfortable and he speaks VERY good English. He is so knowledgeable and told us about everything we were driving by. We learned so much about wine and Italy in general! My favorite fact was that you can only paint houses in Italy variations of white, yellow and red! We then went to a wonderful winery for lunch and wine tasting the he had set up. We ended our day in the cute little town of San Gimignano. Alessandro was truly amazing and so accommodating to our needs. Unfortunately, our 20yo son got a stomach bug the morning we left so he was struggling the entire day. Alessandro was very understanding of our circumstance and all that comes with a stomach bug :(. I would highly recommend his trips to anyone! Thank you for a wonderful day Alessandro!
Review provided by Tripadvisor
Goplaces35610809457
Apr 2, 2025
Amazing Full day tour with Alessandro - Highly recommend a tour with Alessandro! He picked us up at our hotel and provided a nice comfortable ride to Sienna and San Gimignano. He shared great information and history about the area. Before we arrived he had set up a lunch reservation so we didn’t have to worry about picking a restaurant. It was a relaxing day with beautiful sites and amazing views.
Review provided by Tripadvisor
From $123
up to 7 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).