Venice, Milan, Lake Como itinerary suggestions

There are several threads on Northern Italy that can give you some ideas.
I assume you have 7 nights: a typical time allocation would have you spend 3 nights in Venice, 3 on the shores of Lake Como (Varenna is v convenient and scenic), and 2 in Milan.
Where do you fly in/out?

We are flying from Boston. Do you suggest flying to Milan and departing from Venice or vice versa?

If you can easily do so, then yes, otherwise you will need to spend your last night close to where you started.

There are usually some direct flight options into Milan from the US, which make it a good entry point.

if you plan to fly home out of Venice you will often find that the flights leave at the crack of dawn so you will be getting up shortly after you go to bed and need to consider middle-of-the-night transportation options. As well as rubbing what sleep there is out of your eyes.

Conventional wisdom is to fly into Venice and out of the other airport.

8 days isn’t very long so I would definitely fly into one city and out of another to save travel time.
We just flew into Milan and out of Venice with a direct flight to Atlanta on Delta. It left at 11:20 am from Venice which we found very doable.
We found Venice much more crowded than Milan or Lake Como snd we were glad we were not jet lagged as well. Everybody talks about recovering from jet lag in Venice but personally I was glad our two week trip ended rather than began there. It takes more focus to figure out your way around than Milan or Lake Como.

It’s easier to fly IN to Venice than out of although a bit more complicated not impossible
We had a departure at 11 something like Beth and found it easy

Since you’ve been to Venice you might consider just 2 nights there
Lake Como 3
Milan 3 - I haven’t been to Milan but am compiling a list of things to do there and I can see filling 3 nights easily

Another idea fly RT Milan then head to Verona first for 2 or 3 nights before Lake Como

Whatever you decide be sure to allow time to get tested before your departure flight
( although you don’t say when this trip will be)

We are planning for early October.

Then you will likely need to be tested before departure
Don’t think that requirement will be dropped

Are you aware of criteria to enter Italy?

No, I am not aware of requirements to enter Italy. My husband and I are both vaccinated.

Valerie
If you are fully vaccinated you are good to go
Keep an eye on the entry requirements as they may change

You will also need to complete the euPassenger Locator Form

You can use this tool to confirm now and see the official wording
https://infocovid.viaggiaresicuri.it/returningtoitaly.html

You will need to bring your original CDC card- you will need that to board your flight and will need it to enter museums, indoor dining, board trains/ buses etc

And whatever you do- don’t book a flight that transits thru UK- that would require a 5 day quarantine when you get to Italy ( those are rules now)