The Original Plan for the Fellowship?

[Tuor in Gondolin]

I think Aragorn says somewhere he had tentatively planned to go with Frodo and Sam (and Gimli) with Boromir taking Merry and Pippin to Minas Tirith. Not sure about the skate boarding elf. 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.?).

[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.

[Belegorn]

Originally Posted by Tuor in Gondolin

I think Aragorn says somewhere he had tentatively planned to go with Frodo and Sam (and Gimli) with Boromir taking Merry and Pippin to Minas Tirith.

When Frodo went off to think about what he would do they were discussing themselves what to do. The Hobbits were debating whether they should convince Frodo not to go to Mordor if he wanted to go. Aragorn told them that it was the Ring bearer's choice. If Frodo did choose to go, Aragorn said he and Sam would go, and Gimli said he'd go too, and that Merry and Pippin go with Boromir to Gondor with Legolas unless he too chose to go with Frodo.