Last minute trip - can I wing it??

Long story short, I had two other trips in planning that my teen daughter eventually vetoed :)

She has requested a culture/sightseeing/city trip over the 'nature' and 'beach' options. She's had a really tough year and with all the anxiety about heading into high school, I would love to make this happen for her. I have about a month to plan this trip, so here's my first attempt at an itinerary. We will be flying in and out of Rome (only option for a direct flight), which we'll be skipping as we have previously visited:

Day 0: overnight flight into Rome, arrive 7:30 am

Day 1: Rome to Naples via high speed train, Napoli, Overnight in Napoli

Day 2: Pompeii tour, Overnight in Napoli

Day 3: Amalfi coast tour (bus tour or private driver), Overnight in Napoli

Day 4: Napoli in the morning, leave for Florence via high speed train, Overnight in Florence

Day 5: Florence, Overnight in Florence

Day 6: Tuscany day trip (bus tour or private driver), Overnight in Florence

Day 7: Train to Cinque Terre w/ stopover in Pisa, Overnight in CT

Day 8: Cinque Terre, Overnight in Cinque Terre

Day 9: Train to Milan, Overnight in Milan

Day 10: Milan in the morning, train to Venice, Overnight in Venice

Day 11: Venice, Overnight in Venice

Day 12: Venice in the morning, Venice to Rome via high speed train or flight, Overnight Rome near airport

Day 13: fly home

Would love to hear your thoughts:

- We like fast paced, but is it too fast paced? Any suggestions?

- I feel like Milan is a bit of a 'detour' and I wonder if it's worth just for one day?

- Should we get TrainItalia passes? Which one?

- I would love to have some flexibility and not prebook hotels in case we want to linger in one area more - is this too much of a risk? (I wouldn't have considered it but i feel like we could 'wing it' this year?)

- Is there anything else I need to pre-book? (ie. tours, transportation, admission tickets, etc).

Thanks all in advance!

Edited: 11:46 pm, July 10, 2021


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First off- this may be a bit of a 'bouncing around' post. Sorry! Trying to keep it clear...

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I planned to get from Rome to Riomaggiore by train, via Florence, but this isn't booked yet.

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