If you follow the link in the first post hotel names are given. But no names of restaurants.
In the pdf are also hotel names given. For example Villa Condulmer which claims to be a 5 star. Prices on the homepage are around 200 € per night which seems quite low. If you consider they get group tariffs it could work out.
The question of what to make of such a tour is always difficult to answer. For me, it would be a horror. But I also regularly travel to Italy by car and have no problems there. I don't find it particularly difficult either. But if people don't feel comfortable on their own and perhaps don't get on so well, that's not a bad thing. For example, I don't know if I would send my parents to Rome alone today. Of course, things were different 10 or 20 years ago.
As far as the actual trip is concerned, I think a lot of time is wasted on nonsense like a winery or something like that. But then you only have one day in Florence. You don't even go to the Uffizi Gallery, which is a mortal sin. You don't seem to see practically anything in Venice either. But that's all subjective, of course, and interests vary.