I'm currently re-reading Lord of the Rings for the umpteenth time, and a question occurred to me.
When Gandalf hears from Faramir that Frodo and Sam were heading for Cirith Ungol, he is shocked. Obviously, he hadn't planned to take them that way if he had survived Moria. So, what was his plan? We know he couldn't have got into Mordor via the Morannon. Is there any clue anywhere of the route he had been planning to take to get to Mount Doom?
Answer
As Others have already answered, there was no distinct plan other than to send the ring off towards Mordor in hopes of destroying it. Elrond specifically calls this out and suggests that the lack of a plan is a virtue in and of itself:
I think that this task is appointed for you, Frodo; and that if you do not find a way, no one will. This is the hour of the Shire-folk, when they arise from their quiet fields to shake the towers and counsels of the Great. Who of all the Wise could have foreseen it? Or, if they are wise, why should they expect to know it, until the hour has struck?
Before the fellowship departs he cautions:
Look not too far ahead!
The Plan, espoused by the Wise is to not hold too dearly to any one course of action. A loosely formulated plan allows the hand of Providence to play a role in its success. Boromir provides an example of a specific plan, influenced by ideology and carried out by force of will, that goes astray. Boromir's singular goal is to bring the ring to Gondor, unable to deviate from this plan he uses coercion and force to further his plan and ultimately is tempted by the Ring to attack Frodo.
Evil, in the Lord of the Rings is often characterized as unyielding uniformity, a Plan; while Good is aligned with natural and organic processes that deal with change rather than trying to control it. So Gandalf's plan allows events to unfold naturally without the domination of his, or anyone else's will.
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