This is mostly a sanity check, but also a plea for better ideas or reassurance ("you can do this!"). Surely some of you lovely people have done this! The questions are about timing, feasibility, and other possible options.
My family of 4 and another family of 4 (kids are teens) will be flying into Rome, transferring to Positano for the first 4 nights, moving on to Florence for 5 nights, and then wrapping up with 4 nights in Rome (last two weeks of October).
Note: we do not want to drive in Italy (which is the obvious answer to the flexibility we need, but we just don't want to do that for various reasons).
Our plan (as of right now) is to fly into Rome, use the Fiumicino Express bus service to Naples where we'll meet a private van to take us all to Positano (we do not want to take the Circumvesuviana and then buses). I'm assuming I need to book our driver in advance of getting to Italy, not on our way from Rome to Naples. Getting the timing of that reservation right while having to rely on a bus service I know nothing about has me biting my nails. Are there better options? Will I just need to add extra time into our plans for catching the bus so as to properly time the driver meet up? How flexible are most car services with meet up times?
We also want to go to Pompeii while in the area, so we're considering a detour to the site on our way from Positano to Florence instead of taking a day away from our time on the coast. It will make for a very long day, but it's a travel day anyway and it's on our way to Florence, so it seems sensible (is it?). We'd get a driver from Positano to Pompeii, ask the driver to stick around while we do a tour, and then they'd drive us from Pompeii to Naples for the train to Florence. Are there downsides to doing it this way, like is it expensive to have a driver just wait around for you? Of course, I can check with the transfer company, but I'd like to hear from anyone who'd done this first. (If this option is cost prohibitive, we'll have to drop our luggage at a storage area and I'm not too happy about that.)
The rest of the trip is A LOT easier! Just direct trains and more gelato. :-)