Suggestions for my 2 weeks in Italy trip

I think dropping the CT would be a good idea - what you have is an awful lot for only two weeks. Everything on your list is accessible by public transportation. Having a car would be a pain, not only because of the expense and parking difficulties, but also because of ZTLs (areas of cities where you can’t bring a car).

You won’t need or want a car anywhere in your itinerary

A 2 night stay means only one full day
I’d drop Como or CT and to Amalfi

If you want to see the Last Supper start looking now for tickets- not sure if October available yet but they sell out within minutes

I agree that you should forget about using a rental car for any part of your trip. It would be a major headache, and all are doable by public transport. I would also eliminate CT, giving those 2 nights to any of the other places.

However be aware that Praiano has probably the fewest transportation options of the usual AC towns. Since it doesn't have its own ferry dock, you would need to taxi or bus to Positano or Amalfi. Your choice of restaurants will also bs more limited.

Thanks @Cjean for the input on Praiano. I was looking at accomodations etc in Amalfi area and picked that town because it was not as touristy but still able to get to other places. I have to admit that I get motion sickness pretty easily so I was trying to avoid getting on boats if i could. But with that said, how are the ferry rides in that area in terms of being turbulent?

If the seas are too turbulent the ferries won’t run

If your flight home is TBD, I would not go further south than Rome (and conceivably just fly back out of Milan.) Everything until Amalfi/Naples is pretty smooth and easy, it’s a huge outlier. Both coasts in one trip is pretty redundant, so focus on one. The Amalfi Coast is great, but you need more than a couple nights to make it worthwhile.

With that out of the itinerary, you’re still at 4 destinations over two weeks. It might feel a little rushed, but it’s also not crazy. Think carefully about your objectives. Florence in particular, has days of sightseeing packed into it. If you’re not interested in the sights and art, then maybe a couple nights in Lucca or Siena would work better. Alternatively, if you’re very interested in Florence, you might consider making it the focus of this or another future trip.

I don’t see any reason for you to rent a car here. There’s good and frequent train service between all the places. CT will be hardest to get to, but also the one you least want a car for. I don’t think you’ll have a great deal of time for side trips either. You don’t need the complication.

We were in Milan, and did not do the obligatory Last Supper. Plenty of other things to do - Castle Sforsa, roof of the Duomo, interior, museum of La Scala (where you can watch rehearsals).

If you enjoy your drink, Milan had the best apertivo culture. You get your aperol spritz and they give you peanuts or chips or something. One place we got little pizzas.

In 2 weeks, I'd cut my locales to 4. Remember, FOMO means "fear of missing out". You got FOMO. Tame it by spending more time in each place. Florence in particular could stand an extra day, maybe 2. I'd suggest dropping the South and sticking with the northern part. There is Pisa. There is Siena. There is Orvieto. There is Assisi. You have no hill towns near Florence. Add Siena (2 night) and another hill town.

I would advise keeping Lake Como and dropping the CT. I love Lake Como, as it's beautiful and peaceful. Probably add another day to the AC- just traveling to the AC is a full day's experience.
I'm curious- do you have lodging yet? Even October will be a a bit busy, as shoulder season seems to be fading away with this year's surge in travel.
Perhaps share your interests before we advise on " must see" sights.
Safe travels!

I agree with the others and feel you are trying to fit to many locations in two weeks. I think you are better off using the trains and not renting a car as well. I have been to Italy numerous times and I feel you should just go to three locations during your two week visit and really see the sites. I would just visit Milan, Lake Como, Florence and perhaps visit Siena and Pisa (closeby).

The Amalfi Coast has numerous sites to visit, which you could not do in such a short span of time. If you returned on another trip you could do the Amalfi coast and make sure you had time to spend on Capri, see Ravello, visit Pompeii, Herculaneum, etc. This would also be a good opportunity to rent a car and visit the area of Puglia. In Puglia you could visit Alberobello, Locorotondo, Monopoli and Lecce. Italy is so amazing it must be seen in various trips.

Just agreeing with the posters above that you don't need (or even want) a car for your itinerary.

This?

I have to admit that I get motion sickness pretty easily so I was
trying to avoid getting on boats if i could. But with that said, how
are the ferry rides in that area in terms of being turbulent?

I have a stomach like yours and would be FAR more concerned about exploring the Amalfi Coast by road (bus, private driver, etc) than by ferry. The roads are VERY twisty!!! I was positively green just in the back of the transfer van we took between Sorrento and the Naples airport, and that wouldn't be a particularly difficult stretch for most folks with moderately touchy tums. Honestly, choose a location with a ferry dock - which would not be Praiano - and try to do most of your exploring via water. As said above, if the seas are too rough, the ferries don't run but that's been more apt to happen with boats out of Positano's dock than Sorrento, Amalfi, etc.