Okay this is a strange one, at first I thought it was just going to your car 60 times in game but in fact during missions you get a message pop up saying "GO TO CAR " I think you gotta hit 60 of these messages, I went through the game twice and the trophy still didn't unlock. So then I rinsed chapter 1 and 2 over & over until it finally popped, both chapters are really short and easy too...
Hope this helps...