I can't speak for all flights, but our upcoming flight from Venice to PHL leaves at noon.

I agree with StCirq and others and was going to say the same thing...every place you have listed is super touristy. If you are traveling in peak season and want to avoid touristy then skip Italy. We love Rome, been a half dozen times and still can't get enough. As already mentioned, you don't have enough time in most of the places on your itinerary. I would drop something, probably the Amalfi, and start in Rome and work my way North. I personally would get a car in Tuscany. I think it would be faster/more efficient and some trains stop well outside of the town centers where you have to wait for a bus. But not everyone is comfortable driving so it depends on personal preference.

If you plan on tasting any wines, either make sure you know how to sip-and-spit or take a tour.

"I did say not ALL, but most do leave very early AM."

I checked the departure board for today and the first (and only) flight departing VCE to the US is Delta to JFK at 13:20. Maybe these very early flights janisj is talking about are seasonal.

Seasonal flights to the US that I found

AA
Chicago, dep 14:55
Phl: dep 12:00

Delta
JFK: 13:20
Atlanta dep: 11:10

United
Newark dep: 11:05

But if you're heading to the West Coast and some other destinations in the U.S., you would probably choose to connect in Europe, and the first flight would have an early departure time. Taking a non-stop to somewhere on the East Coast first can add a few hours to the overall travel time. Just speaking from experience....

Google flights search, Mid May, VCE to SFO, one stop, total duration less than 20hrs
Some, but by no means all or even most flights depart early.

J62 -- I did say most but NOT all. Of your list of 5 flights, 3 would have one having to leave their hotel between 3 and 6 AM. And the only one with a comfortable departure time is on Gawd awful Untied.

No, not all, but the majority have very early ETD's

Sheez. You're arguing over flight times available out of Venice... and they are planning to CUT Venice from the itinerary! We should be "arguing" about that

Hi everyone, thanks for the replies!

To clarify what I mean by touristy, it's not just about the number of tourists. I've been to Rome before and I didn't really enjoy my time there. I've been to many other European cities that were packed with tourists and I enjoyed them more. Regardless, we are reconsidering staying in Rome longer. Here's our revised itinerary:

Night 01 - In transit
Night 02 - Rome
Night 03 - Rome
Night 04 - Rome
Night 05 - Amalfi Coast
Night 06 - Amalfi Coast
Night 07 - Amalfi Coast
Night 08 - Amalfi Coast
Night 09 - Bologna
Night 10 - Bologna
Night 11 - Modena
Night 12 - Florence
Night 13 - Florence
Night 14 - Florence
Night 15 - Florence
Night 16 - In Transit

We've added a night. We've also cut out Naples, but we may still try to grab some pizza when we stop there on our way to the Amalfi Coast. Right now Venice is still not on the list but all of this outrage may very well convince us to reconsider. The only way I can see us making it work would be to very sadly take out Bologna. The wife really wants to go to the Amalfi Coast so that's non-negotiable.

OK -- so WHY does she want to go and WHAT does she want to do? Your current plan would allow you to see a few things, but not to see all of the highlights of the area. I'm not saying your plan can't work, just that we can't comment intelligently without more information.

Everyone, of course , has different opinions. In essence, most Italian "touristy" places are that way because they are so special many tourists want to go there. I absolutely love Rome, but a trip there takes enough days to enjoy it. Almost everyone I've met that said they didn't like Rome is because they spent just a few days.
Naples is, IMHO, not worth the time being taken away from other possibilities. Amalfi is pretty, but if it's raining, it's a big loss.If it's a must, pray for nice weather.
I like Bologna more than Modena (although we stay at a great place just outside Modena), but no comparison to Florence.
have fun planning.

Apr 4th itinerary looks swell.

I'm just surprised about the number of days in different places. Like Florence getting more time than Rome. You have 4 full days worth of things you want to see in Florence?

No one says you have to go to Venice -lol- to dismiss it because of being "too touristy" is what I objected to (i wouldn't call it "outrage" really )

Q--OP says they are using Florence as a base for "We're hoping to explore wine country while in Tuscany. Would we need to rent a car for this?"

When asked, my rule of thumb is Rome needs, at least, 2 more nights than Florence and Florence needs one more night than Venice.