So for this trophy, you want to basically go all the way up to Little Tipworth. That way all the shortcut gates are open, all you have to do is go through them and that is it. You need to go through all 5 and can be done in any order once they are opened.
Here is a video to show you where to go and help you along the way.
Credit for the video goes to PS4Trophies from Youtube.