Italy in November or June/July

I have only ever been to Italy (4 trips over time) in the period from July to November. Whilst July is hot, I found the November weather depressing, and would expect December to be more so. Note that it may not be a choice of hot vs cool, but hot vs cool and wet. You have articulated the choice well, so it's up to the both of you.

Holly, I've been to Italy a few times in November and December. This year I'm returning on November 20th and will be there till December 10th. The weather is pretty temperate and, even though I live in south Florida, I found the temperatures to be pleasant. More importantly, the crowds are gone. I'm able to travel at any time of year and I refuse to visit from mid-May till the end of October just to avoid the heat and the throngs of tourists.

A issue to consider is that your days will be much shorter as you approach the shortest day so you will have more hours of darkness than sunshine. You can be sure it will be hot to very hot with some humidity in July. Nov can be chilly but it can also be nice. It just depends. You hit one of the weather apps and see what the average daily temp is in Nov. Given your choice I would think Nov works best for you. The discussion of crowds in Rome is crowded and very crowded. I don't I have ever been in Rome when the crowds were not substantial 'cause a lot of people live in Rome.

Thanks for the replies, I will definitely have to consult with my friend who is coming with me as we have very different weather preferences. Definitely want to avoid large crowds, so will have to take that into consideration as well.

Lodging will be cheaper as well In November.
I can see the weather being more unpleasant the further north you go like in Venice.

As a comparison with the heat in an Australian summer, and yes Brisbane and Melbourne are way different, however the heat of the day is less relentless in Italy compared to here. Even after a hot middle of the day, the late afternoon and evening can be very pleasant, especially in the north.
If you minimised time in the south during late June ... Rome > Siena > Pisa > Florence
Then maximised your time in the north during early July ... Venice > Verona > L Como > Milan

November/December weather can vary quite a bit. Layers, warm socks, a jacket (perhaps with a zip out lining?) that is rain-repellant might be a good idea for you.

Lots to do after dark, although museums won't have extended hours.

Summer can be miserable while November is moderate in my opinion. November and December are my favorite months in Venice particularly as the crowds are thin. You can always put on a sweater or a coat and raise an umbrella and carry on. It's harder to go on in the heat. And it seldom rains all day!

Ahhhh the ever changing weather. I remember leaving warm Rome one October and arriving in Florence where it was freezing in our hotel. We inquired about heat (we had a student who was ill) only to be told that they had just turned off their air conditioning for the season and wouldn't be able to turn the heat on for a few more days. We just asked for extra blankets for the chilled student.

It was like switching from summer to chilly autum in that one day. If you do go in the fall it might be desirable to start with your most Northern city first and work to your most Southern location, tracking the hopefully temperate weather south.

I was in a warm Berlin once in October, travelled to Prague for the weekend, before returning to a freezing Brrrrrrrlin.