Private Tuscany Tour From Florence Including Siena, San Gimignano And Chianti Wine Region

Was expecting a guide and historic details about the places planned for the visit. We ended up with a driver (smoker, sick and coughing the whole time) who really did not provide any in depth information about the places planned. Further the trip mentioned an optional wine visit that we could schedule or the driver could recommend. We were surprised at a more formal booking at a winery that we did not enjoy, did not have any detail on whether we were supposed to pay or not. I had questions because I was confused on a number of options such as the pickup point (I had provided our hotel information at time of booking) as well as questions about the wine tasting. The operator was not responsive - did not provide any response on the wine tasting, and only confirmed the pickup point after they texted me and said pickup was in central Florence and hotel pickup could be arranged for a fee. For a price close to $1,000 USD I cannot recommend this tour nor this operator. You will find so many better options I am sure whether a group tour or even renting a car for a day. We would never book through this operator again.

Placedo was very knowledgeable and made excellent recommendations when we told him we wanted to focus the tour on wineries. Excellent all around.

This trip and experience was a highlight of our families trip! Diego was very knowledgeable and also so kind in helping us plan our visits and the overall day - our family had the best day escaping the crowds of Florence!

The driver did a nice job; however, we would have preferred a longer time in Sienna and the other Tuscan town. Those stops were incredibly rushed. It would have been better to leave off the last winery! It would be nice to have that option on the front in and get to choose. We do not feel it was worth the expense.

Placido was a great driver and we really enjoyed his commentary and conversation! Our only disappointment is having so little time in Sienna and San Gimignano. We would have preferred more time in the towns and given up the last stop at the winery. We can tour a winery at home.

Placido could not have been a more pleasant, amenable and helpful tour driver and guide. Our trip went as planned and Placido enhanced it with his wealth of personal knowledge and his ability to be flexible and creative. The only thing that might have been different was when I called customer service a month ago for help with adding on a lunch or wine tasting, if the telephone customer service person could have be more knowledgeable about the Tuscany Tour in general so as to advise us more intelligently. We ended up with 2 wine tastings which was nice but unexpected and unnecessary.

Christian was fantastic! Super friendly and informative. We had a great day. The sites were amazing and the tours were exactly what we were hoping for. Very well organized.

This tour was amazing. Placido is an excellent driver and his years of experience in the area gave him a wealth of knowledge he shared with us. He was on time and professional. This excursion and Placido made this day trip a highlight of our Italian adventure. I would not hesitate to book this again. We were traveling with elderly low mobility parents and his kindness and attention is greatly appreciated. I cannot say enough on how special this was. Thank you.

⭐️⭐️⭐️⭐️⭐️ A Truly Outstanding Guide — Cristian Made Our Day Unforgettable During our stay in Florence, we had the absolute privilege of spending a full 10 hours with Cristian as our private tour guide, and I can say without hesitation that he is one of the best guides I have ever had—if not the best. Cristian took us from Florence to Pisa, through the Tuscan countryside, and into Siena and San Gimignano, delivering an experience that was nothing short of extraordinary. His professionalism stood out from the very beginning, but what truly elevated the day was his deep knowledge, warm personality, and unmatched level of care. Every stop came alive through his insight. Every question was answered with expertise. Every request—big or small—was met with genuine accommodation and enthusiasm. I’ve been on many tours around the world, and Cristian ranks at the very top. He is friendly, engaging, and incredibly thoughtful, striking the perfect balance between guiding, educating, and giving us space to enjoy each moment. His passion for Tuscany and its history shines through in everything he does. To Cristian’s supervisor: you have an exceptional asset on your team. To future travelers: if you have the chance to tour with Cristian, take it—you will be grateful you did. Cristian, thank you for an unforgettable day. Your dedication and kindness made our time in Italy truly special.

Drive was exceptional to the locations. Views were picture perfect. Given enough freedom to explore. Lunch was amazing.

Booked a custom private Tour which included additional locations versus standard private tour. Alessia gave very quick responses to get the tour priced and booked. Had a great day with our driver Diego and we hit all our timings and objectives for the visit. Highly recommended.

We enjoyed too much and we highly recommend this trip to everyone. We saw a lot of beautiful places and countrysides, the winery visit to chianti region was perfect. We tasted a lot of wine and they were all great.

It was a great day for the 8 of us in our group. Our driver arranged lunch at a small winery where the owner gave us a tasting of his wines with lunch so we ended up with an extra wine tasting, a nice surprise.

Very personal tour with Christian. He shared information about the Chianti region. Our winery experiences were lovely.

Everything was perfect!We had a great time!Our driver was very professional!

Christian was a superior guide. Happy to be with us, enthusiastic, and very knowledgeable. The Tuscan countryside was breathtaking. The lunch and wine tasting far exceeded wine tastings we had in Napa Valley. We had high hopes for this day, and thanks to Christian they were exceeded. We had a marvelous trip to Italy, and this was the best day of all.

We really enjoyed our experience through the rolling hills and through beautiful countryside. Sangimigno was awesome. I have never seen scenery with that combination of hills, cypress trees and vineyards before. Our driver Placido was friendly, knowledgeable, and a great driver. He knew all the good spots for photos and he never rushed us. We are very happy to have taken this private tour.

We had a fantastic time on our tour today. Christian was a great driver and guide. We worked out a great plan for the day up front and made some adjustments along the way. He is very knowledgeable and personable.

T was very friendly, accommodating and kind We enjoyed our experience and he helped to tailor it based on what we wanted to do

Fantastic day trip! Our driver Valentin was the best! He arrived at our hotel in a beautiful Mercedes Benz. As he drove us to each city, he provided a brief history about where we were going to visit. At each city we had plenty of free time to roam around and enjoy. Our last stop was the winery. We had a wonderful time sipping the various wines. However, when we were given the last wine to taste, the waitress didn’t even allow us 5 minutes to enjoy it. She said “let me guide downstairs as your hour is up”. To be honest, we would never do the wine tasting again. We felt they cared more about selling wine than allowing the guest to have a nice experience. Overall, we give it 5 stars because of Valentin and the beautiful cities we visited but not the wine tasting.

Our tour with guide, Cristian, exceeded our expectations. Not only was the scenery wonderful, Cristian was enthusiastic, knowledgeable and tailored the private trip to our needs. We enjoyed the experience to such a degree that we had Cristian again for another tour two days later. Bruce S and Ann H, Vancouver, Canada

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!

Cristian was a fantastic tour guide. A lot of information and great recommendations for the group. He picked out a great spot for lunch at a small family winery. Totally worth the experience and would recommend to anyone visiting the Florence/Tuscany region. We had so much wine and food! 10/10!

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

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.

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.

Valentin was a fabulous tour guide. He was the perfect fit for our group of four. He was completely engaging and we so enjoyed our conversations. We weren’t rushed at all and Valentin had great suggestions for what to see and do in each town.

Placido was a fabulous host and we thoroughly enjoyed our private tour. Lunch at the farmhouse/artisan winery was brilliant.

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.

We had a great time with Placido. He was very knowledgeable about Tuscan history. He customized our trip based on our abilities. He took us to see all the best Tuscany had to offer. We had a beautiful wine tasting and lunch at a Tuscan winery. Placido was patient, and went the extra mile. He even made time for a little shopping. As a guide, he was the best a tourist could have. We will be using him again most definitely.

Christian, our guide, provided an excellent and professional tour of San Gimignano, Siena, and the Chianti wine country. He was very detailed and knowledgeable about the history and sites throughout the day. We especially appreciated that he took the initiative to include extra stops at scenic viewpoints which enhanced our experience. Furthermore, he was courteous enough to offer to take photos for our group, ensuring everyone was in the pictures. His efforts consistently maximized our time and the overall enjoyment of the trip.

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!

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!!

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.

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.

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.

Highly recommend the private tour! We were guided and enjoyed a full day with Christian. Very enthusiastic and knowledgeable, the car ride to the sites were engaging and we were fully educated on the sites, traditions, etc before arriving. Trust me , this added immensely to the experience. - the beauty of Sienna, San Gimignano were ineffable. Experience for yoursel. - Christian arranged a 'once in a lifetime' wine tasting and lunch in Chianti at a 3rd generation wine 'fattoria' - San Appiano. The tour, wine tasting, scenery will be everything you had hoped for. Trust me, go ahead and get the private tour and you will save time and get 5x the experience for your time.

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.

Cristian, our fantastic guide, took us on an incredible tour of the Chianti region that included stops at two charming family vineyards. The scenery was amazing and Cristian went out of his way to make our experience memorable. Highly recommend

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.

Great views! Amazing tour guide. Our bus driver on the other hand, coughed for the entire tour. Did not cover his mouth. Unlucky for me who sat right behind him, 3 days later got sick with the flu (spent the last 3 days of my trip in bed, missed out on tours that had been booked cause I couldn't get out of bed) and now I have bronchitis possibly pneumonia

The views were spectacular and it was interesting to learn about the wine vineyards history. Our tour guide Cristian was very informative and did a great job of explaining the history of all the squares that we visited.

Our guide Valentine was so nice and courteous and explained everything to us. He answered all of our questions too! He also recommended a beautiful winery to have lunch in. The views were incredible!

Our private tour to a Tuscany winery, Siena, and San Gimignano with Cristian was an absolute highlight of our trip! From start to finish, Cristian was incredibly knowledgeable, engaging, and genuinely passionate about sharing the beauty and history of Tuscany. He tailored the experience perfectly to our interests, recommending an exquisite winery, navigating us seamlessly through charming Siena, and ensuring we had ample time to explore the breathtaking San Gimignano. We can't recommend him highly enough – a truly exceptional guide!

Cristian was our tour guide and he was so enjoyable!! He explained everything so well and knew so much of the history. We listened to try to remember all of the info. He made our tour!!

Placido, our driver, was prompt, friendly, experienced and helpful. He gave us plans for our visit that were easy to follow. Our trip to the Siena Duomo was quite memorable. The special lunch he arranged for us was excellent!

What a fabulous day with Cristian touring Siena, San Gimignano and the Chianti wine region! Our guide was the best! As a native Florentine, he was very knowledgeable about the region and provided great commentary. We were picked up at our hotel and transported in a comfortable Mercedes vehicle. The scenery was gorgeous and the stops along the way provided us a window into the many aspects of Tuscany. Cristian was so professional and accommodating. Safe driver too! We highly recommend this private tour!

Valentine was very kind., informative & very safe driver. He gave us great tips at each location we stopped & made us feel like friends. We had a wonderful day!

Cristian was an amazing tour guide! We were able to customize parts of our tour and Cristian did a fantastic job of educating us along the way! We were able to go to boutique, family run vineyards and historic towns all in one day. Would recommend!