@mchookem, this is fun to watch come together and I am glad to see it shaping up.
My advice (toss it or use it) to anyone going to Europe is this— once you have the basic sketch, you should CUT activities and destinations before you try to fit any more in. I know that’s painful as you look at a trip like this but it has always paid off for me. Getting the most in and having great photos ends up being more rewarding for your friends than for you personally. Seeing the Med is awesome, but even more awesome is just to give up a bit and experience where you are.
If you are finding a day or block of time, my best advice is to simply not fill it. In your case, I’d just leave unscheduled time in Florence or Rome. You can wander around, you can go back and get deeper into a place that caught your eye, you can do a last minute side trip that you didn’t think about. But you won’t regret it. In nearly all my travels in Europe, the unscheduled “let’s see what comes up” have been the best.
Except when my kids demanded another aquarium. Fuck that. There are fish in the U.S.