There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.
After about 40 minutes by bus, arrive in Monteriggioni, a charming medieval fortress set atop a hill. Enjoy 45 minutes of free time to stroll through the village squares and soak up its timeless atmosphere. Guests may also choose to walk along the fortress walls (optional, extra cost).
Continue to Siena, one of Tuscany’s most beautiful historic cities. Guests who select the Classic Tour option will enjoy a 1-hour guided walking tour with a professional guide, focusing on the city’s main highlights (exterior visits only). Guests with the Semi-Independent option will have approximately 2.5 hours of free time to explore Siena at their own pace.
During the guided tour, admire Piazza del Campo from the outside, one of Europe’s most stunning medieval squares. Your guide will explain its unique shell shape and its role as the setting of the famous Palio horse race, as well as the exterior of the Palazzo Pubblico and the Torre del Mangia.
The final stop of the Siena visit is the Siena Cathedral, admired from the outside. Learn about this magnificent example of Italian Gothic architecture, renowned for its intricate marble façade.
After lunch, travel on to San Gimignano, the medieval town famous for its skyline of towers. Enjoy free time to wander through its cobblestone streets, browse local shops, or relax with a coffee in one of the charming squares.
During your free time, you may choose to visit the Collegiata, the town’s main church, known for its well-preserved frescoes and Romanesque architecture (entrance optional).
During your free time in San Gimignano, you may choose to stop at the famous Gelateria Dondoli, an award-winning gelato shop located in the main square. This is a great opportunity to taste some of Italy’s most renowned artisanal gelato (not included in the tour price).
In the evening, relax on the journey back to Florence, bringing an unforgettable day in Tuscany to a close.
Ceci was really nice, helpful and clear about instructions. It was nice to have a day that just took care of itself and the wine tasting was very fun!
Ceci was a wonderful guide. She is very sweet and helpful. I definitely recommend this tour!
Lovely experience ..the cathedral in Sienna was stunning..gimigniano was charming As was our guide
Really nice tour and really nice experience with Daisy and Cosimo. Totally recommended!
So much fun! Very cool to see different cities in one day
Roberto, Lucia & Raul are an excellent team ... very knowledgeable about the Tuscan region, personable, communicate well before, during & after the tour, and considered our safety at all times. Highly recommend this tour.
We had an amazing time on this tour! Raoul our driver and our tour leaders Roberto and Luccia were wonderful and so helpful. They made sure to keep us safe and together. The admission fee was well worth everything that was included. It was about 10 hours but didn’t feel like it dragged on. The group atmosphere was great. The crowd size was good and didn’t feel like it was too big. This tour is well suited for any age group/ability as you could opt out on going to places with many steps etc. Highly recommend this tour and this team. Thank you Roberto, Luccia, and Raoul!
Lots to do and see. Only negative is I came back 15m and no bus. Very scary would have been nice if you said bus koves on Whats App feed.
It was a pleasant experience. It run smoothly with no issues. I just wished we has got to San Gimignano earlier
We enjoyed the day trip while we were in florence area, our guide Constantine, he is amazing.
The day was very efficiently organised with good timings for each stop, ensuring there was no time to get bored. Saw some amazing medieval architecture and beautiful sights. The guided walk through Siena was well worth paying for and the wine tasting was a lot of fun. The whole day passed in no time.
Very well organised by Camila, Ignatio and Raul.
The team was amazing and did an incredible job touring us around Tuscany! All the stops were well organized and provided such a unique experience. The trip had each stop the perfect amount of time to experience as much as you can. Couldn’t recommend this tour more!
Great it was fun and great we had a Great Time
We had a wonderful experience, the guide gives good instructions, the bus is comfortable.
Had an awesome day on the tour! Everyone who work this tour was great!
Good selection of tuscany llaces to visit
very beautiful your!! 10/10 would recommend :)
The timings are really good, no time to get bored. The guided tour of Siena was really good, very informative . The guides throughout the day Camella , Raul and Ignazio , were helpful and kind. The wine tasting was a highlight. Thank you for a lovely day.
I joined CiaoFlorence's Tuscany day trip on September 29, visiting Monteriggioni, Siena, a Chianti winery, and San Gimignano. It turned out to be one of the highlights of my stay in Florence! What made the experience especially memorable was our tour leader, Diana. She was friendly, knowledgeable, enthusiastic, and had a great sense of humor. Throughout the journey, she shared interesting stories, historical facts, and local legends in both English and French, starting almost as soon as we left Florence. As a solo traveler, I especially appreciated her personal attention. Diana took the time to chat with me, asked about my travels, and even let me carry the group's flag for a while! We also had a lovely conversation about our backgrounds and languages. These little moments made the tour feel much more personal rather than just another large group excursion. The itinerary was excellent for discovering several beautiful places in one day. Monteriggioni was a charming first stop, and Siena was fascinating. My €75 ticket already included a guided walking tour of Siena with a separate English-speaking local guide and headsets. The guide was knowledgeable, although I would have liked the walk to last a little longer, as it felt quite short and the streets were crowded. I also chose the optional group lunch for €22. There was a generous selection of dishes, including bruschetta, pasta, and other food, followed by gelato. It was a decent, filling lunch, although naturally not quite the same experience as dining at a good restaurant independently. The wine tasting at Poggio ai Laghi was another interesting experience, even though I'm not usually much of a wine drinker. I enjoyed trying the wines, but the presentation felt quite sales-oriented at times. Some claims about the wines being completely natural and not causing hangovers sounded rather exaggerated to me, and the bottles offered for sale seemed expensive. San Gimignano was beautiful, and I was happy to finally try gelato at the famous Gelateria Dondoli! There was enough time for a stroll, although visitors wanting to climb the towers or explore museums would probably appreciate a longer stop. There were a few minor organizational hiccups, including some initial confusion at the meeting point and a short wait for the bus after San Gimignano, but nothing that significantly affected the day. Our driver also did a great job throughout the journey. Another thing I really appreciated was that Diana continued sharing useful recommendations even on the way back to Florence, including where to find good pizza and how to recognize quality gelato. She also played some music and took song requests, which created a relaxed, friendly atmosphere after a long day. Her enthusiasm never seemed to fade! Overall, it was a fantastic, memorable day and a great introduction to Tuscany. I would definitely recommend this tour to anyone wanting to discover several beautiful Tuscan towns without having to organize all the transportation themselves. Thank you so much to Diana, our driver, and the entire CiaoFlorence team for such a lovely experience!
Lucy & Anastasia were great hosts. They were very kind patient and accommodating. Money well spent with the tour and well timed arrangements for the trip.
Amazing value for money. Wine tasting alone - great day!
Great trip. Knowledgeable and orient guides.
Guide Alex, THE BEST!! Awesome day full of history, exciting views and a great taste of wine.
Camilla was exceptional in the way she managed so many languages and a large crowd of 70! She was ably supported by Jon Marco. Luca made it such a smooth journey…. Thanks to them and the beauty of the three towns we visited, as well as the wine tasting, this will be a day we will remember forever!!
Great experience. Recommended. Very happy. Camilla and Juan Marco were very helpful. Thx.
Camilla and Gianmarco were great! She translated in 3 languages and took care of us. I had a good time and I feel that the time allocated to each place was sufficient
Lovely day, great information knowledgable and helpful staff
We have done three tours in Florence and this had the most value. We had four amazing stops, and the wine tasting was phenomenal! The bus was so comfortable. It was worth every penny.
The tour was timely and very well organized. The bus was clean and comfortable. The towns visited were incredible. The tour of Sienna with the local guide was excellent. Weinstein was a blast! The only negative was that there was a lot of dead time on the bus and with the other guides that could have been used to actually inform us about the history and culture of the places we visited.
Alex was the best guide! The tour was relaxing and enjoyable. Perfect time to explore each stop. Alex was knowledgeable and brought great energy to the whole day. Filipa was also very pleasant. Tour was a good coverage id highlights of Tuscany countryside.
Good experience guide was good very well managed
Simply an amazing tour with Freddy and Roberto. Very well-organized, with clear explanations in 3 languages. Nice must-dos proposed at each stop.
We had a brilliant day trip with our guide, Roberto and driver, Freddie. Roberto kept everyone organised and informed which made the day really easy and enjoyable. The coach and drive was very comfortable and the planned stops were great. Along the way, we were given lots of guidance and recommendations, and if you wanted, you were also able to book lunch which Roberto organised for you. We enjoyed the option of being able to have our own freedom, and trying out all the recommendations provided - all were spot on and we'd happily visit them all again!
Very good experience a little difficult walking but I had a bad knee . Coach was comfortable. Guides were very good especially Roberto . Highly recommend.
We had a great experience today expertly led by Roberto and our driver Freddy. The day ran seamless with many great suggestions about how to maximise our visit to each location. Bravo Guys!
We had a great time on the tour from Florence to Sienna, San Gimignano, Monteriggioni and Chanti wine tasting. Our tour leader Roberto and our bus driver Fredy were very professional and everything went smoothly as per schedule. Thanks to them, we were able to see and experience the beautiful Tuscany in just one day. Roberto provided us with great information about the region and gave us great advice what to see in our free time. Excellent communication and clear instructions re: meeting places, Highly recommend.
Roberto was amazing! He gives all the details about the tours and he was supermprofessioonal. Freddy was a good driver too. Thank you very much!
Experience was great. The guide was very knowledgeable. Very patient and did a great job. You can tell she loves her job.! highly recommend anybody to do this tour.
Chiara was a great group lear and guide. Really liked all the towns that we visited and the wine tasting was exquisite.
Great, very nice day, had a good time
Amazing guide and service must go
Guide excellent (Chiara). Really lovely. The tour in Siena, even though the man who did the tour was great, it was super short. Only one street. Not sure if that was worth it. Some areas were not really crowded which was nice. To enter the basilica, as the floor was uncovered, you had to pay 10€ as well as if you wanted to go to the towers in the villages. Overall it was a nice tour specially for the guide and because the weather was good. Not a lot of cover if it was raining
We were a group of 4 and had a great day out of Florence. The English bus was full, so we were placed on the Spanish-speaking coach, but our guide kindly switched to English for us and looked after us all day. We chose the option without a local guide or included lunch in Siena. The free time there was perfect for doing our own thing: the Duomo, with its marble floor uncovered, then lunch at a little spot we found ourselves. The included lunch looked like excellent value and would suit anyone who’d rather not hunt for a place to eat, but we enjoyed exploring. Each to their own! A festival in Monteriggioni meant that stop was swapped for extra time in San Gimignano, which we didn’t mind at all. Next was the Chianti winery, a real highlight. We arrived early, tasted grapes straight off the vine, then sampled four wines, from a sparkling white to a classic Sangiovese and a rosé, with salami, bread and some lovely vinegars. We finished the day in San Gimignano, with its medieval towers and fantastic gelato. Excellent value and easy, with no driving or logistics to think about. Highly recommend!
Good informative trip. Guides and staff were nice too. ................,............................
We have taken many Viator tours before, and most of our experiences have been good. Unfortunately, this tour was a significant disappointment. The English-speaking group had over 40 people, and the tour leader walked too quickly in Siena. Many participants, including older travelers, struggled to keep up, and some fell behind or became separated. Multiple audio headsets also did not work, resulting in wasted time troubleshooting equipment and regrouping. We missed a significant amount of the guided commentary, and valuable time that should have been spent enjoying the destinations was lost. We paid for a guided tour, not just transportation between towns. The poor group management, equipment problems, and rushed itinerary substantially diminished the experience. We were also charged €13 each for regular Siena Cathedral admission tickets, while the same tickets were available independently for €10 each. The operator later clarified that the service was advance ticket purchase, not skip-the-line access. Viator/Tour company offered a 20% partial refund for the audio issues but declined to address our broader concerns through additional compensation. Given the combination of poor organization, missed commentary, and lost sightseeing time, we would not recommend this tour. It was a disappointing outlier among the many Viator tours we have taken.
Lucia, Maya, and Raul made our tour seamless from start to finish. Their meeting instructions after every stop were crystal clear, taking all the stress out of exploring on our own during free time. Lucia was extremely knowledgeable and patient, working closely with Maya to navigate a large group through busy tourist areas. The entire day was exceptionally well organized. The itinerary hit all the right notes: a quick stretch break at a castle, Siena tour and nearly two hours for lunch and wandering, a wine tasting, and ending the day with incredible gelato in a medieval town. A full day trip well worth it in a comfortable private bus with a/c.
We had an amazing family trip through the beautiful Tuscan countryside! The places we visited were absolutely stunning, and the entire tour was perfectly organized, with excellent timing and a very comfortable experience. Special thanks to Ignacio and our driver Mario, who were both incredibly attentive, friendly, and professional. Their positive attitude and willingness to help made our day even more enjoyable. A fantastic experience for the whole family. Highly recommended! We would definitely do it again
The whole experience was extremely well structured throughout the day for every location. We received plenty of recommendations for the day from our guide. The winery locations was extraordinary but what we loved the most was our last location of the day San Gimignano. Siena was a great visit too. If you're interested in architecture and a great vibe, that's a place you must see. Our guide Roberto was extremely flexible and professional alongside out coats driver Valentin . They are really a great duo. Don't hesitate booking this trip with them!!!
We truly enjoyed the entire trip. Everything was well organized, and we really appreciated your kindness, professionalism, and thoughtful care throughout the day. Thank drive Valentin and tour leader Roberto Date: October 8th
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