Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from Florence.
Piazza della Cisterna is a charming medieval square situated in the heart of San Gimignano. Surrounded by well-preserved medieval towers and historic buildings, the square takes its name from the ancient cistern located at its center. The triangular-shaped square is paved with medieval stones and exudes a timeless atmosphere. With its well-preserved medieval architecture and unique charm, Piazza della Cisterna stands as a captivating focal point within the UNESCO World Heritage site of San Gimignano.
These well-preserved walls, dating back to the 13th century, served both defensive and symbolic purposes. The "Mura" offer a scenic stroll along their length, providing panoramic views of the charming town, its iconic towers, and the picturesque Tuscan countryside.
Step inside a storybook fortress village encircled by intact walls and ramparts, beloved by filmmakers and history fans alike. Enjoy free time to browse tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Join a guided walking tour (if option selected) through contrade banners, artisan storefronts, and grand palazzi that reveal Siena’s golden age. Afterward, enjoy free time to sip an espresso, browse boutiques, or continue exploring this Gothic masterpiece at your own pace.
Piazza del Campo is the main square of Siena, famous for its distinctive shell shape and elegant brick pavement. Surrounded by historic buildings, it is home to the Palazzo Pubblico and the Torre del Mangia. It is also the setting for the famous Palio di Siena, a historic horse race between the city’s districts.
Cathedral Entrance and inside guided visit only if option selected - officially known as the Cathedral of Santa Maria Assunta, is a stunning medieval cathedral in Siena. Renowned for its distinctive Gothic architecture, the cathedral showcases a magnificent facade adorned with intricate sculptures. Inside, visitors can marvel at remarkable works of art, including frescoes, mosaics, and statues by renowned artists like Donatello and Michelangelo. The cathedral's breathtaking interior also features a striking marble pavement and a magnificent Piccolomini Library.
Only if cathedral entrance option is selected - The Piccolomini Library, housed within the Duomo di Siena, is a Renaissance gem adorned with vibrant frescoes by Pinturicchio. Commissioned by Pope Pius III, these artworks depict scenes from his life, creating a cultural and artistic treasure within the Siena Cathedral.
My sister and I had a fantastic day exploring San Gìmignano and Siena and a delicious lunch at il Ciliegio vineyard. Aaron, our tour guide and Francesco, our driver, were friendly, fun, and informative. We had plenty of time to explore and shop and felt that it was a great value. I highly recommend the tour.
Aaron was amazing and the bus driver. He let us know where the toilets were and if we had to pay or not. Also very enthusiastic on giving history of the areas we visited and passed by on the bus.
This was our second time on this tour. We loved San Gimignano and Siena so much that we had to come back. Aaron and Francesco were amazing guides.
Such a great experience! Our tour guide was fantastic! Would recommend!
Stella and Silvio provided a great experience. I highly recommend them both!
Amazing Guide Stella!! One of my favorite day excursions I’ve ever been on throughout Europe.
Great experience with Martha. She is so knowledgeable and so cute
Fantastic experiencie!! Aaron and Federica were really great. The tour is perfect - well balanced in time, and the lunch at the vinícola was really nice and happy!
Aaron did an amazing job. He spoke very fluently in both english and spanish and always kept the group full of joy and energy. Frederica also did a great job getting us to and from each location timely and safe. Would highly recommend.
Aaron is the very best. And our bus driver was excellent. Would do this tour again and would highly recommend
Fantastic day trip, our guide Aaron was very knowledgeable
Our bus broke down right before we headed to Siena after our lunch at the winery. But Aaron, our guide, was cool, calm and collected the entire time. He updated us and made sure we were all safe. He also made sure we got to Siena regardless! Thank you Aaron for your knowledge and friendly manner. We will never forget this experience!
Martha was an absolutely wonderful tour guide! She was so friendly, knowledgeable and professional, making the whole day a real pleasure. We feel so lucky to have had her as our guide! Visiting three cities in one day was absolutely worth it, and the wine tasting was a fantastic experience. If you love wine, it’s definitely not to be missed. Highly recommended!
It was a truly enriching experience from start to finish. Tuscany is unbelievably beautiful. If possible, a richer lunch would be appreciated — it's a long day.
An experience to be had. Our guide Marta and driver Sylvio were very good. Marta kept on sharing information in detail about the places we were visiting. She was very jovial and kept everyone in good spirits. The trip was perfectly planned with good time at all places. A personal suggestion 3 hrs in Sienna was a bit too much and should be reduced to 2 hrs. Also at Winery if a proper farm visit or a trip to the wine making facility is arranged will enhance the experience. Trip is recommended not to be missed.
Marta was very cordial, professional and fun…. Our driver, Silvio was a wonderful and safe driver.
Very good tour guide and experience!
Marta and Sylvio were amazing. The whole trip was well organised and really enjoyable. Marta was so lovely and so approachable the whole day!
We love the trip, excellent guide Marta led the way. She had an incredible talent of saying her message in Italian, English & Spanish every time. So knowledgeable and friendly.
We had an enjoyable adventure. The sights were fabulous and the history fascinating. The tour crew were outstanding. Christiana and Keiko kept us informed and engaged. And Antonio transported us safely.
The tour was great! Christiana and Keiko were amazing guides. They efficiently fit a lot of great things in one day.
Amazing experience, totally worth it! Extremely well planned and executed. Thanks to Christiana, Keiko and Antonio for making our trip enjoyable :)
Christiana and Kate were great!! We didn’t have tixs for the basilica but they got them for us at the last minute!! The other guide had good information but talked so long that we were only in the church was a short time. Less info and more time in the church
We saw some great scenery and had a nice lunch at the winery. The tour guides were knowledgeable and fluent in multiple languages. The tour group was a lot larger than I thought it would be. A double decker bus stuffed with people and all the information given twice. Once in English and once in Spanish.
We loved our tour - it is such good value for money! Martha and Louisa were amazing guides, full of really interesting facts about Tuscany. The guide around Siena was also amazing - I learned so much that I would never know without the tour. I would recommend this tour to anyone - It’s a long day but worth every penny. Thank you so much!
Our guides Martha, Louisa, and driver Carmine were awesome and friendly. The whole tour went smoothly. Information and instructions provided were clear. We enjoyed ourselves.
Had such a great time. Went to amazing places and the guides were amazing and knowledgeable! Thanks to Marta, Louise & Carmine for an incredible experience.
Marta , Luis and the bus driver. Thanks for all the tour and explanantions!
Marta was a great guide! The lunch at the winery was really good
Excellent experience in terms of scenic beauty, hospitality, your planning and guiding services. Martha and Louisa were so good and prompt with all recommendations and their knowledge and explanation style was amazing for every place we covered. The lunch at Chianti vineyard was an experience of lifetime with amazing appetizer, entree and dessert with 3-4 types of wine tasting. Lastly, our driver Carmine was amazing with the navigation, choosing the most scenic route. Extremely value for money and highly memorable.
Excelent experiencies and nice places
Martha was amazing! Carmine was a great driver!
The transportation was excellent, time in each stage was reasonably good but fitting everything in a single day isn’t easy, but it was worth every penny.
This full day excursion into Chianti Region was excellent. Guides were fine, the bus was comfortable but no bathroom on board.
The tour was nice. Our tour guides were Stella and Cristina. We recommend it. A great way to see more of Tuscany!
The trip was as expected and an easy day with well guided tours and leaders. The wine tasting was a very good experience for the wine but food was average. The tour company is prompt, well spoken in multiple languages, and very friendly. It was a bigger tour than we expected but we likely missed the details in the description. The 2 ladies that helped us along for the day were just amazing!!
The tour went well and as smooth as we hoped. Our tour guides, Stella and Christina were very informative and made sure everyone was comfortable. Everyone enjoyed the tour and we will definitely consider CAF tours again when in Tuscany.
Great day, made friends. Had great wine & beautiful scenery. The bus was relaxing & had wi-fi.
Very friendly people, both the guides and the driver were awesome.
Excellent! Highly highly recommend
This is a good budget friendly option to visit the Tuscany region by Florence. You are packed into a double decker tour bus with a ton of other tourists but I didn’t think it was too bad. All the cities you visit are gorgeous and our local guide in Siena was great (Bettina). They give you plenty of time in each city to stroll and go shopping for souvenirs. Never felt like it was rushed or too much time was given. Only thing is you’re sent to a massive tourist trap for lunch. Poggio ai Laghi is the winery you go to, has decent reviews on The Fork but the wines and oils are incredibly overpriced for grocery store quality (if that) wine. It was around €50 per bottle of wine or oil. The food was also worse than Olive Garden. It’s edible but very mushy (way overcooked pasta) and plain (“ragu” sauce was bland). At least it was something you could bond over with other tourists on the bus over this. (One person said they could make something better at home). As long as you’re good with that, it’s not a bad option. Otherwise look for a semi private or small group option.
Good experience with good Tuscany towns. Cathedral tour option was nice and you still got free time in Siena. Guide was clear on meeting points and times at each stop.
Aaron and Christine were fabulous. We didn’t realize it was such a big group tour but it worked for us. They made sure everyone was accounted for and gave very detailed information to make sure everyone made it back to meeting places. Aaron gave amazing information prior to getting to locations with a nice sense of humor. It was a long day but so worth it.
Great experience! An easy and well planned way to see the beautiful countryside without having to worry about logistics. Silvio was a fantastic driver, Christina did a great job keeping an eye on everyone (it’s a large group but you have a lot of free time), and Aaron was engaging and informative. I felt the time in each place was well planned. The winery lunch was fantastic; a full meal (image just of appetizer). Enough free time, views, shopping, and winery experience. I highly recommend if you’re not driving on your trip! Thanks Silvio, Aaron and Christine!
Aaron was a great guide who kept us informed and on time. The tour was very large (60+ people) but a lot of time was on our own, which was good. I enjoyed all the locations but you are on the move. It makes me want to do a smaller tour with a more personalized wine tasting experience next time.
Aaron and Cristina were excellent tour guides from Florence. The stops were all very scenic and easily walkable, lots of places to take pictures and buy souvenirs. They provide plenty of time in each town to wander on your own, never felt rushed or like there was too much time. The guide in Siena was excellent for giving history and information about the town and cathedral (Bettina). The wine tasting and lunch, on the other hand, were not so great and sadly not skippable. Wines were maybe grocery store quality if I’m being generous but was asking around €50-60. Balsamic vinegars and oils were around the same pricepoints as the wines. The food was about the same quality as Olive Garden but smaller portions and quite disappointing. Definitely a tourist trap. The bus driver (Silvio) did a great job getting us from Florence to each of the towns, especially the turn at Monterigionni. You do go on a big double decker tour bus though, so if that’s not your thing, look for a semi-private or small group option. Overall, it was a good tour experience.
Aaron , Christina were amazing and very kind. The overall experience was very good and would recommend other people the same. Thanks guys
Nice trip with Aaron, Christina and Silvio. Local guide from Sienna was really interesting and we had a good moment at the vine yard.
Very good one day trip. Aaron and his team truly made the trip very comfortable, and organized.
Wonderful! Aaron, Cristina and Silvio were fantastic. It was very organize, even with a huge group. Lunch was included and excellent. Well worth it.
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