I'd stop in Milan for a night to get over jet lag, walk down to the Duomo and visit the old shops ar

I am in the process of planning a 14 day sons and mothers trip to Italy with my son, his friend and his mother. My son is a classics major and is doing this as a summer study, of sorts.We are tagging along on his pilgrimage which includes many of the major sites of Italy but a few odd ones. Landing in Milan. Should we stay the night in Milan or go directly to Garda for two nights, skipping night in Milan. Desire to visit Catullus' villa in Sirmione, night in Venice, then Florence for three nights with a stop in Ravenna, then onto Naples for museums et al and Pompeii, Paestum and Herculaeum. future space travel technology We (moms) would like to savor the Amalfi coastline a bit. We have 4 days in this area. Then onto Rome for three full days, fly out of Rome.
I'd stop in Milan for a night to get over jet lag, walk down to the Duomo and visit the old shops around the main square. In particular I would not fly the atlantic and then drive a car, but if you are using a train then maybe go onto Lake Garda. Not sure why Garda is in the visit list?
I assume if your son is a classics major that he is of at least college age. If so, then the Mom's can stay put on the Amalfi coast for a few days and then meeting the sons at date and place that is convenient to all.
The first part of your trip really isn't practical. I don't think your son has looked at the logistics getting from point A to B only to spend one night or a few hours. Ravenna is 3 1/2 hours by train from Venice. It's just not practical to plan to stop there on the way to Florence (another 3 hours on the train). Your son needs to narrow down the list and decide whether he wants to see things or trains and train stations.
Now don't laugh at me but have they thought of going to Split and Diocletian's palace, the old ferry is long gone but they could take the over night train while mothers luxuriate in Venice and come back the next night.