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Last map of the sea-route before I go to sleep.
I interpreted the second, furthermost brown dot on the OP's map as a cave or a very small town. So I put in an island which has both.
The island at the very end of the route is representative of Thursday Island, the most populous of the Torres Strait Islands. I have not yet put all the finishing touches on the little town, but I think I've got a workable general layout here.
Thoughts?