The Original Plan for the Fellowship?

[William Cloud Hicklin]

Originally Posted by Tuor in Gondolin

It makes sense to take a dwarf to help getting through the borders (probably by some underground passage---did Aragorn know about Shelob and Co.?).

Aragorn had interviewed Gollum (or been present when Gandalf did so) and knew that Smeagol had gone in and come out. I doubt Gollum actually said how or gave directions, but the Ranger probably reckoned that if there was a way he could find it.

Moreover, Aragorn had spent time in Gondor, and it's clear from Faramir's comments that something at least was known of Cirith Ungol. Now, whether Aragorn would have dared bring the Ring so close to Minas Morgul is another question.