Traveling in Novmeber for 10days in italy

Italy is a big country, and your question is too general to attempt to answer. I think you need to do more research and see what interests you. My "bests" could be a snooze for you. Watch the RS Videos, get a guide book, Draft an itinerary, and then ask for more specific advice. Enjoy the planning.

Here's a place to start:
https://www.ricksteves.com/europe/italy
Se what appeals to YOU.

How many nights will you sleep in IT? What airports are you flying into and out of?

Personally, I would choose a city or cities with many museums and cafes in case it’s raining or cold. Maybe one or more of the big 3: Venice, Florence and/pr Rome. Each of those is wonderful in every month.

We're in the planning stages of our trip in November. We are flying into Venice and going to Florence and Sorrento. My 4th trip but it's been a while. As others said, it depends on what interests you. We're planning some museums, some relaxation and lots of walking and eating.

*Milan, yes, my wife loves high fashion.
*Rome,I'm enthused with Rome and its history as a believer in Christ although I'm not catholic.
*Naples, we love pizza and its origin.
Florence ????
Venice, I hear this can be seen in one day, but my wife would love the canals and boat rides.

With 10 days without the traveling to and from. We are wondering if 5 city's may be to much we don't want to feel like its work, haha

I’m assuming you have not bought your plane tickets so fly into one city and out the other which is known as multi-city (open jaw) when booking your flights. All five cities have airports so check what city pairs are the cheapest and then decide on where to go. If you choose to fly home from Venice, make sure it is not an early morning flight to avoid a costly water taxi ride from your hotel to the airport.
Don’t expect to do much on arrival day except settle in. With that said Milan deserves two nights, Rome five nights and that includes a day trip to Naples on the fast train. Florence and Venice three nights.

IMHO, Venice cannot be " done" in one day. If you try that, you'll hate it.

How many NIGHTS will you have on the ground in Italy?

To get 10 full days you need 11 nights

If that is all you have then 5 cities is too many
Pick 3, 4 at the most

You can’t go wrong with the popular
Venice-Florence-Rome itinerary

If you must go to Milan
Fly to Milan
Milan 2 nights
Train to Venice 3 nights
Train to Florence 2 nights ( no time for day trips)
Train to Rome 3 nights
Fly home from Rome

If you have 11 nights add a night to Florence or Rome

According to this post you’ve already allotted 4 days for Milan - that would be 5 nghts
https://community.ricksteves.com/travel-forum/italy/looking-for-the-best-fashion-exsperiance-in-november-for-mialn-we-will-be-here-4days

There are so many places to see in Italy. I do think that Pisa is worth a couple of hours at the Leaning Tower site.
I also think you might be advised that the length of time to "do" a place is so personal.

I once visited both Pisa and Florence in the same day, enough to get the immersion and vibe of each place. Not to any great detail, yet sufficient to have enjoyed myself.

Venice is my favourite Italian city for tourism. I recommend staying on Lido island. The view of the city from the Vaporetto is amazing as you cross the lagoon.

I am not a fan of Milan. Yes the Duomo cathedral is pretty., I think you will be underwhelmed with the rest? You could see the Duomo whilst changing trains from somewhere better to somewhere even better.

I adore the coastine from basically Rome all the way to St Tropez in France through Pisa, Genova, San Remo, Monaco, Nice and Cannes That would be a memorable trip and can be done by train.

You are welcome to PM me for more travel tips...

source European expert former travel agent, age 60, living in the UK and have visited all of Europe, lots of Asia and USA