Trip Stop Advice - Rome/Florence/Venice/Como/Milan

Option 4: Rome 3 nights, Florence 4 nights, Venice 4 nights, Milan 2 nights

To be transparent, I have not been to Lake Como in 5 trips to Italy. Too many good things to see elsewhere and, to me, Venice is more of a draw. If you must do Como, then drop Venice. It's your vacation. :D
I only give Rome 3 nights since you say you'll go back and it's easy to add a few days to Rome since you're most likely to fly into/out of there.

Start checking flights and see if any deals pop up to any particular entry/exit city. It's so easy to get around by train, I wouldn't pay a pile extra just to do a multi-trip, but it's always good to check because it might not be any extra. Our next trip, flights were cheapest into and out of Rome, so we're training to Venice on arrival. A prior trip, we got great business class fares to and from Milan, so we arrived and trained directly to our first stop and then spent a couple of days at the end in Milan.

If you are going back, I would probably skip Como this time too. However, if it's a must, I spent one day (no nights) in Milan the first time I was there (I've been 3 times, which I mention bc it gave me perspective on that one day/first time) and did a lot and felt really satisfied. We arrived in Milan at around 8:30 am and departed around 5p, and walked all day. We saw the Duomo and Last Supper and walked so thoroughly around. On subsequent trips we did much the same but walked farther afield, and I was impressed by how familiar I was with everything from that one day. So you could do Rome 3, Florence 3, Venice 3, Como 2, and Milan 1. That's a rushed trip. I would probably do Rome 4, Florence 3, Como 3, and Milan 2, only because I get burnt out on city city city city. I like to plan city country city country etc when possible, so Como would be a breather.

Como is a must do per my wife so I don’t see us cutting that. I think the 1 night in Milan is possible.

How does this sound?

Rome (3) Florence (3) Venice (3) Como (3) Milan (1)

Have you thought about flying into Milan, going to Lake Como, and then working your way south and flying out of Rome?

We are wanting to fly out of Milan on Emirates 5th Freedom using points. We want to do that last since it will be in business class.

Personally I would pick 3 locations for longer stays. Your travel days will basically cost you a half day of travel each time. That and transporting luggage would make it less enjoyable for me. I understand the thought of seeing the locations, but ultimately it is a vacation. I think a slower pace suits me. Just my opinion..

We just returned from some of your proposed cities. I do need to write a Trip Report, but a few initial thoughts-

We love Lake Como, have been to Varenna before, but it's getting too crowded, just like the CT and Amalfi. Sadly, we won't return. The regional trains and ferries can't handle the crowds, (basically don't try), and there's no shoulder season anymore. The influencers seem responsible, and it's intolerable by mid-afternoon. It's also getting expensive and difficult to find reasonably- priced accommodations. I'll attach the previous threads. This is all pretty sad.

Avoid at all costs the holidays and weekends around them. We ran into May 1 ( Thursday) holiday crowds, which extended into the weekend. Also avoid the full week before and after Easter. I believe April 25 is also a holiday- the Italians have many.

We love Venice, and stay away from St Marks Square, so don't experience the crowds. We love the Cannaregio area, and Hotel Ai Mori d' oriente, on the quiet back canals. Will return again. I would stay four nights here. Many options for day trips out of Venice.

Not a big fan of Milan, except for flying into/ out of and sleeping over. Hotel Berna is great for this.

We used Milan Linate airport, in town, with much easier access than Malpensa, which is 45 min express train out of the city center.
So- maybe Rome, Florence, Venice, and overnight in Milan?

Have a great trip!
https://community.ricksteves.com/travel-forum/italy/is-lake-como-getting-crowded-like-the-ct-and-ac

https://community.ricksteves.com/travel-forum/italy/private-transfer-from-varenna-to-milan-centrale