Had the same confusion with this trophy so leaving this here:
I think you can be locked out from getting all the "Travel" stories if you progress too far because the bird is one of the characters that tells some of the stories and you lose him after finishing the last quest (he goes back to his kingdom) ... so without him those stories don't seem to get told no matter how many times you rest at the camp fire. I had to reload an older save where i still had him.