Hi we will be in Milan for a convention for 5 days and have 5 days before going home,
is the weather too bad or is it too far to drive to Rome and make stops in-between?
Is the truffle season on?any suggestions?

We will be traveling by mid November

Are you saying you have an additional five days after your time in Milan? If so I would definitely say go to Rome. I would not drive there, take the train. Very fast and efficient and having a car in either of those cities is a major PIA. If you wanted to see some of the region between Milan and Rome then a car could be useful, but if you only have a total of five days it's probably not a good idea. Book the five days in Rome and if after a couple days you are bored (highly doubtful) you could do a day trip (also by train) to someplace. Orvieto is a good choice of a day trip from Rome (1 hr by train) that has a bit of small town feel. Another option would be to split the time between Rome and Florence but I would still opt for just Rome.

If you want truffles you should skip the idea of going to Rome and go to Piemonte instead. You will find truffles there in abundance, especially if you rent a car and visit the countryside. However, you should also be able to get plenty of nice truffle meals in Milan's better restaurants. Many of the best truffles of the Piemonte area are sold to Milan restaurants (because that's where the money is!)

The weather in November anywhere in Italy can be intensely rainy, especially in the first 3 weeks. It is not a time that I would plan a driving trip where I was forced to keep driving because I had a plane to catch hundreds of kilometeres away.

Since November is not a very, very busy tourist time in Italy, something you might consider is taking the train from Milan to Florence, and booking a hotel for two nights. If the weather turns out to be fantastically dry and sunny, rent a car and spend the next 2 nights in the countryside, heading to Rome. Drop off the car in Chiusi or Oriveto and take the train to Rome.

If the weather turns out to be horrible, skip the idea of driving to Rome and either get on a train and go to Rome and enjoy some indoor activities (or stay in Florence and take a day trip by train to Pisa or Bologna or Arezzo, etc).

You could do the same substituting Torino in Piemonte for Florence. Book 2 nights in Torino, rent a car if it is glorious weather and visit the hills and wine country and eat truffles -- but then I'm afraid you need to go back to Torino to drop off the car and take a longer train ride to Rome. It would work much better if you were flying out of Milan.

wow thank you very much on the insight.
So maybe not a definite plan is the idea?
If it is wet Florence and/or Rome by train.
If it is dry the Piamonte, Torino and Verona ?

I think committing yourself to a definite driving plan is not a good idea. Anyplace you want to go by train is fine. But rain can be so intense in November that you really don't want to be committed to driving until you can see a short-term weather forecast.

If you want to combine Torino and Verona then I very much recommend doing that by train, not renting a car. Also, while I think everybody would agree that Torino has many day's worth of indoor activities for rainy days, there are fewer in Verona. It is mostly a city enjoyed walking around outdoors. Florence is a very good "rainy days" city. Bologna is good too for rainy days, with a number of unusual museums and covered streets. It's only an hour from Milan. Rome also has plenty of indoor activities, and from Milan, it's 3.5 hours by fast train.

Thank you very much, I think we have a good idea of our options and will be making plans once we are there as advised.