My boyfriend, mother, 9 year old son, and myself will be traveling to Italy for the first time the beginning of November. (It is also our first time out of the United States.) We are aware that it is the rainier season etc but it is the option we have for our work schedules.
My thoughts are to fly from Portland, Oregon into Rome and out of either Milan or Venice. (We have a concert in Milan on one night.) I am planning on being away, including travel, for 2- 2 1/2 weeks. I had wanted to make it to Venice, Florence, Rome, Naples (Pompeii actually) and Sicily. After the reading that I have done, I am thinking I will need to cut a couple things out or maybe just Sicily. I have also read that Naples is not worth visiting. Any opinions? I really think Pompeii and Versuvius would be amazing to see. But, I do have to make it as far north as Milan for the concert. And how many nights do you think we should stay at each? I don't want to cut the time too short for seeing the sights but also don't want to plan more time than needed in a particular city.
I am traveling with a 9 year old and hope that he will not be terribly bored but any suggestions would be great.
I had thought that we would stay in places found on AirBnB but have also read it is not worth it if you are not staying at least a week at a time. Again, thoughts or suggestions?
Anything would be helpful at this point. We do not have a budget per say, however, we like to balance if we can by saving when possible and splurging when it is important to us. Thanks in advance!!!