In general, the trip was fantastic. A few observations:
The waiter thing was very hard to pin down. We'd get great food and great service, but it sometimes felt like you need to tackle the waiter and put him in a headlock before you got your check.
Venice was my favorite. Yes, it's a little tourist-y, but wandering the streets & canals is dreamlike. You feel like you are in a magical labyrinth. I couldn't stop taking pictures because every step you take, you see a scene that's picture-worthy.
All the food I ate was good, but the best thing I ate was a Porchetta sandwich with crispy pig skin at a festival in the mountain village of Corvara. Sublime.
I put a lot of energy in trying to track down the best Gelato. But, in truth, that's probably unnecessary. I went to at least 10 different places and all of it was excellent.
Rome was great, but I don't think I ever got used to the "head on a constant swivel" mentality you need when u walk around the back streets to avoid getting run over lol.
I will never ever go back to Italy in the Summer. It hit 100 multiple days in Rome. Not fun.
This may be a weird thing to observe, but it was striking how many Italian restaurants there were. It was a very high percentage. Even in the more non-tourist areas. I guess gastronomical variety isn't as important over there for the average Italian?
The people of Italy were just wonderful. They were a pleasure to be around.
Public transportation was good (trains) & fairly easy to figure out for a non-native speaker.
For some reason, Euros have a distinct monopoly-money feel.
I did several "skip-the-line" tours & in all cases, they were totally worth it.
You could not pay me enough, to drive there in the cities. Just madness. Parking was an adventure because you were never entirely sure what a sign meant However, we drove a bit through the countryside and that was fine.