Exclusive Assisi & Cortona: Private Day Trip from Florence

We opted for the two hour guided tour of Assisi and that was the best decision. She was so knowledgeable and helped direct us on what do with our free time. Would have liked more time in Cortona. More to see there than expected. Our driver, Luca, was also very knowledgeable and had great input

Easy to book- Professional driver who was pleasant and flexible. Plenty of time to see each site built into the day. It was a good value for the day and ease of process and trip.

Stellar service, easy way to see historical sites. Plenty of time to spend in both places and the private driver was professional, timely and a pleasure.

We recently booked three days of private tours and transfers through Ciao Florence for our family, totaling close to $4,000 USD. As a travel advisor coordinating this experience with Beatrice from Private Experiences and Events department on behalf of my own family, I found the communication process difficult. Responses typically took at least 48 hours, which made it challenging to finalize details and respond to my client’s (and family’s) questions in a timely manner. On the day of our first scheduled tour, my mother had a fall at the train station and required medical evaluation. Despite this unexpected event, Ciao Florence stated there would be no refund and that additional charges would apply to reschedule, which felt disappointing and insensitive given the situation. Thankfully, our experience with Cristian, our private tour guide, helped turn things around. Cristian was kind, knowledgeable, professional, and attentive throughout both tour days. He explained the day’s plan clearly, welcomed our input, and made thoughtful additions to the itinerary. As a family interested in Catholic pilgrimage, he took us to the Franciscan Hermitage after our visit to Assisi, which became a deeply meaningful highlight for us. On our second day, he suggested a wonderful winery for lunch and called ahead to ensure the staff was ready for us with a tasting, tour, and table—all handled with genuine care. Cristian was consistently on time and clearly respected by the local guides he worked with. While the itinerary from Ciao Florence mentioned that Wi-Fi and bottled water would be provided, these were not included. Cristian’s hospitality and professionalism were the bright spots in an otherwise bumpy planning process. He deserves five stars. The company’s communication and policies, however, left a lot to be desired.

Cristian was an amazing guide. Went over and above to make our day one of the most memorable experiences in Italy. Thank you for everything Cristian.

This was a perfect tour for us. We prefer to wander about on our own rather than with a tour group. Leonardo, our driver, was excellent. We had over 2 hours of free time in each location. Had a great lunch in Cortona at Leonardo's suggestion. Would definitely go with this company again.

Gabriele lead an amazing tour and was well-informed on each of the locations. Definitely recommend booking this trip!

Really enjoyed the trip to Orvieto and Assisi. Our guide Gabriele was super friendly. Assisi was beautiful, worth making the trek from Florence. Very spiritual places, the tour was heavily focussed around the churches.

Our driver, Tisiano, met us at our hotel in Florence and drove us to Assisi, and then to Cortona. He knew the important parts of St. Francis' story, and stopped at the Portiuncula sanctuary before arriving in the town of Assisi. We so appreciated that, because we really weren't sure of what we should see. We were free to roam in Assisi and then met our driver at an appointed time. We then drove to Cortona and stayed for an hour or so--it's a very beautiful town. Before returning to Floe also stopped at an old church that our driver particularly likes which is very beautiful. Tisiano was punctual and professional and really just a wonderful person. We had a great day!

If I could give our driver OSWALDO 10 stars I would. Omg he was so kind. He changed our stops a little bit to accommodate us and explained everything. When we were ready to be picked up he was always there waiting for us. It was a fantastic day. ASSISSI is so beautiful