Not to discourage you too much but at least a year working the ramp. Then the problem is which operator will give the chance to somebody from Italy when there are so many pilots from the local area looking for jobs. It may be that Canada is easier for low time pilots to start out as compared to Europe, but if your not from here it will be that much more of an uphill battle (that is even if you can get a work Visa). On the other hand where I work there are two pilots from France and one from Belgium. Though they did all there training here and have all lived here for a decade. So if you want to do it badly enough it is possible, just don't expect to jump on a plane and get off in the Canadian north and expect to be flying in the Canadian bush overnight.