There should be no considering at this point. Its one thing to say, "I'm going to miss you, I wish I could go to Italy with you!" It's entirely different to say, "Hey, don't go."
This guy is concerned with himself, and obviously would rather have you turn down once-in-a-lifetime opportunities so you can make him happy instead.
Drop him. Do it before you miss out on anything else. There are more than enough guys out there who would be willing and able to support your dreams, not talk you out of them.