Admittedly, I've already spoiled myself by looking at Omega Krypton's "solution", but here's one plausible method to find it legitimately:
OP also indicated that there was a second meaning to the title. Well, even after finding the solution (sorta) legitimately, I still don't have any idea what else it could mean. Some thoughts:
I have 2 possible answers. But let me try this one first.
The writer's going to
The writer here is
As pointed by @oleslaw,
The texts 'i sail eastwards' and 'musings of nights spent oblivious of need' possibly refers to:
The answer corresponds with Hint 3:
Still working on some of the clues, but I may have a lead on some.
Don't get sidetracked - this is probably Denver's first
Don't get side tracked
This is probably Denver's first
Name the cartoon bear that loved honey.