We usually do pretty well on site. Although with some of the signs, they sometimes seem to alternate what they tell you. Magic Kingdom this way, then next sign is for Magic Kingdom resorts. Then next sign says Magic Kingdom again. You have to pay close attention.
But last year, right after Christmas were visiting relatives in Cocoa Beach and headed over to Gaylord hotel to see huge ice show. Got there just fine. But in attempting to get back on Osceola and then Greenway, ended up on Disney property not once, but twice. Apparently problem was I could not remember whether I wanted to go north or south on Greenway. (the road, of course, actually goes AROUND the southern half of Orlando and both seem to terminate around I-4, so are you going north on the Tampa side or going north on the Daytona side? It took me two tries to figure it out.