Plane tickets are booked for Italy. We have a rough itinerary but still debating on a few things before starting to book, probably gonna book the train tickets and the Sicily flights after as well. The order is going to change as I saw Serie A starts on August 20th, going to try and work around to be in Milan on that date now.
Basically the plan is 4 days on the Amalfi Coast, 1 in Pompei, 1 in Naples, 4 days Rome, 1 day Assisi, 3 days Milan, 1 day Venice, 3 days Sicily, 4 days Florence.
The big debate was spend more time up North and or some time checking out Lake Como and some of the mountain area's or Sicily. Timewise we couldnt do both and we ended up settling on Sicily. The flights are super reasonable - basically can fly there and to whereever we need after for about 150$ cad.