I contacted Massimo after finding the many positive reviews online. My requirements were quite specific, being a multi-city itinerary for a solo traveller, and each day involved different sights I wanted to visit. Massimo was attentive and thoughtful from the start, explaining how some requests were not possible, how to balance out the attractions to get the most out of each day, and so on. Once the final itinerary was agreed upon, he took care of all logistics (car transfers, tickets, guides), with the exception of hotels and restaurants (I had my own preferences for these; however, he could give recommendations if needed).
Once in Italy, he kept track of the trip at all times, and made sure I was dropped off/picked up at the predetermined times and places. He was always available to sort out unexpected issues, and for last-minute changes to the itinerary if he thought it would fit the situation better (within reason). For example, as happened multiple times during my trip, if we had some time to spare (even half an hour), he would offer to take me to an attraction close by to pass the time, instead of waiting idly. There is the option to be more hands-off as well, if you say you prefer to do some exploring on yourself.
I was also fortunate to have Massimo as my driver, and he was a very easy person to talk to, full of interesting stories and cheer. The trip included a lot of driving (Milan -> Venice -> Florence -> Pisa -> Florence -> Rome -> Naples -> Rome), and the time passed by quickly with such an entertaining host.
In summary I would unreservedly recommend Massimo and Best Tour Of Italy for any Italy trip. He has great pride in his work and does everything he can to make sure you have a good time. Of course this is more expensive than a group tour or self-arranged tour, but you essentially get a tour tailored to your requirements, where all logistcs are taken care of, leaving you with what you want to do - seeing the sights of Italy.