In order to get the "Out of the Deepening Darkness" trophy in Burly Men at Sea, you need to wear the barrels, win against the Grim Reaper and head left to avoid the maelstrom.
(Remember to make cross saves before trophy related decisions to drastically speed up your play throughs).
Here's the steps from when you enter the Whale, which is an unavoidable incident at the very beginning of the game:
-- Talk to the girls by the fire
-- Go all the way left until you see three barrels, interact with them
-- Interact with them again after the dialogue
-- Head right and go through the door behind your ship
-- Scroll right, get through the dialogue
-- Interact with the uvula, get through the dialogue
At this point you'll get:
-- Swim right, dialogue
-- Scroll right, dialogue
-- Move the cursor to the Grim Reaper and hold X until he falls back to last place (you don't need to follow him with the cursor once you are holding X)
At this point you'll get:
-- Swim right, dialogue
-- Hold L2 (or L on Vita) to escape the maelstrom, dialogue
At this point you will unlock the trophy. You can now exit back to your ship via the main menu rather than finishing the game if you would like, for a quicker route to alternate trophies.