Fly out of Milan versus Venice

Can you fly into Venice and out of Florence?

It could be cold, just prepare for it and you’ll be fine. We spent 2 weeks in December from Rome to Venice many years ago and we were bundled up pretty much the whole time. I much prefer it to the heat, though.

That would be the ideal and what I originally wanted to do, but the place I wanted to stay in Florence is booked for the last week of December. Seems like the nice places at a decent price are booking up already during the holiday. My husband works at a school, so not much flexibility.

Weather probably better than at home and less likely to have rain.

A 6AM flight .... UGGGGHH

(A vote for Milan)

I've gone to Venice flying into and out of Milan. Nothing to it. It was also in December and I ended up going to a Sunday night soccer match, AC Milan vs Napoli. Wasn't that cold.

There isn’t much difference in temperature in December between the Seattle area and.Northern Italy, just less rain in Italy. Coming back to the US is always a pain since flights depart in the morning. Flying out of Milan would not be any different, since there are no flights from Milan to Seattle and the Malpensa airport is even farther from Milan than the Venice airport from Venice. Unless you want to visit Milan I wouldn’t bother.

I have wanted to see the Last Supper, so if not much hassle and the same difference either way, airport hotel, I kinda figured, why not.

Sure, why not. If the weather's good (no wind or rain), you can roam around the roof of the Duomo, and walk through the lovely Galleria Vittorio Emanuele II (enclosed so even in the rain . . . ). From there it's a short walk to La Scala.

Milan is never a bad idea, and changing hotels for your last night is less hassle than waking up at 2 (or staying up all night) to get to Venice airport...

For our Veneto trip in 2019, we flew into Verona and out of Venice, going through Amsterdam both ways. Our flight from Venice left at 4:55pm --- it might be interesting for you to see which European hubs you can get to with a later flight from Venice and compare the time spent on the train to Milan and a pre-flight hotel (which, yes, is perfectly easy and we've done that, too) vs the stopover time in Amsterdam or elsewhere. Just another idea! It sounds as though you'd really like to see the Last Supper and Duomo in Milan!

We've never been cold in either Florence or Venice in December, but Venice can be foggy (and beautiful) or just humid, so avoid wearing cotton (which gets damp and stays damp) --- layers of wool, down, and various miracle fibers are your friends. I wear my down coat just while boarding the plane, then put it into a soft bag or pillowcase and use it for a pillow.

"Milan is never a bad idea"

Ah, music to my ears!

An advantage for Milan is that there are likely more options for direct flights to the US from there.

I have done early flights home from both Venice and Milan and, to me, its about the same. When I had a 6:00am flight out of Venice I used Motoscavi private taxi to meet me at the dock near my hotel and shuttle me straight to the airport dock. I believe they picked me up around 3:30am and the trip cost about 100 Euro. I had a 6:40am flight out of Milan and we used Suntransfers as our private taxi and it also cost around 100 Euro. There may be more flight options out of Milan so if you are looking to sleep a little later Milan may be your best bet. We have an upcoming trip to the Cinque Terre and we are spending our last 2 nights in Milan because Genoa, Pisa and Florence airports didn't offer the flight options we were looking for. This will be my 3rd time in Milan and each trip has been 2-3 days at the tail end of a trip. I think Milan is easily seen in 2-3 days but we always plan to return so we don't feel rushed to see everything.
Good luck with whatever you decide.