I am a professional tour director and my work takes me all over the world. I currently live in the United States but I would like to move to Italy. It will take some time for me to get an permanent visa but my work would probably ensure that I am not in Italy for more than 90 days in an 180 day period. It’s a lot to juggle though and would mean turning down jobs in Italy so as not to go over my allotted time. Which would be a shame because I do speak Italian. However, I do have two passports. Would I be able to enter Italy on my US passport, hit the 90 day mark, head to France or Switzerland for the weekend and re-enter using my Canadian passport for another 90 days within that same 180 period?