Tuscany Medieval Towns Tour with Wine Tasting

We had an excellent Tuscany tour arranged by Ciao Travels. Everything was organized smoothly from start to finish, making the entire experience enjoyable and stress-free. A special thanks to Lucia, Marco, their associates, and our bus driver for their outstanding hospitality, professionalism, and constant support throughout the trip. They were always helpful, attentive, and ensured that everyone was comfortable and well taken care of. Despite the extreme heat and humidity, the team did everything possible to keep us comfortable and make the tour enjoyable. Their careful planning, local knowledge, and friendly attitude made the experience truly memorable. I highly recommend Ciao Travels to anyone planning to visit Tuscany. If you are looking for a well-organized tour with wonderful guides and an unforgettable wine-tasting experience, this is an excellent choice.

The tour took us to some beautiful places, and the tour leader was friendly and hospitable throughout the day. However, she explained at the start that she was a tour leader rather than a guide, so she would not be providing detailed commentary or guided tours at each location. We chose not to purchase the optional guided tour of Siena or the additional lunch. While we appreciated having free time to explore Siena independently, we felt that those who didn’t purchase the optional extras were not given the same level of attention or engagement. As a result, the experience felt more like transportation between destinations with drop-offs, rather than a guided exploration of the region. We would have expected a more consistent level of service and engagement for all guests, regardless of whether they purchased optional add-ons, and at times we felt like outsiders on the tour. The highlight of the day was the winery visit. The host leading the wine tasting was fantastic—engaging, knowledgeable, interactive, and genuinely made an effort to get to know everyone, which created a welcoming and enjoyable atmosphere. Finally, while Monteriggioni was charming, there was relatively little to do there. We would have preferred to spend less time in Monteriggioni and instead have had more time in one of the other villages or at the winery.

We had a fantastic day exploring Tuscany! Roberto was an excellent guide, and Valentin did a great job getting us from place to place safely and on time. Communication was clear throughout the day, and Roberto shared lots of interesting facts without making the tour feel overwhelming. I really appreciated that there were several opportunities to personalize the experience, like adding the guided tour of Siena or choosing your own lunch. One of my favourite stops was San Gimignano, where we met a lovely couple who own Cecca. Their pinions were AMAZING! And the gelato stops Roberto recommended in San Gimignano were to die for! I also loved the medieval music Roberto played between stops. It was such a fun touch and really added to the atmosphere as we drove through the Tuscan countryside. If I could change one thing, I'd personally love a little more time in San Gimignano, but that's just because I enjoyed it so much. Overall, the pacing of the day was excellent. Even though it was a full-day tour, it never felt like we were stuck on the bus. It was a great balance of driving, walking, and free time, especially in the summer heat. I'd definitely recommend this tour!

This was such an amazing tour! Our guide, Roberto and driver Valentin did an amazing job! They made us feel safe and were extremely helpful! The places we visited sure absolutely stunning and the wine tour was superb! Highly recommend if you're ever in Florence!

Excellent tour! Did not feel rushed and had plenty of time to explore each city (Monteriggioni, Siena and San Gimignano). Our guide Roberto provided great details on both places during the bus ride and did very well managing both sharing in English and Spanish. Our driver Valentin drove very smoothly and kept the bus very cool which was great for a summer tour.