To what extend did Istari know Middle-earth?

[Morthoron]

Originally Posted by William Cloud Hicklin

Given the context of that quote, I had always assumed the reference was to Valinor, not to the Great Lands

I'm thinking the Elves in Valinor wouldn't necessarily need promptings of wisdom or fair things, would they? Unless, of course, we are talking about just prior to the Kinslaying.

There is precedent of many Maiar (Melian being one who remained) and a Valar (Orome along with his entourage) visiting the Elves in the 1st Age. It's not like they had any prohibitions in that early age of Arda. Olorin in spirit form would not require a ship as a conveyance.

Consider this quote:

"That Olorin, as was possible for one of the Maiar, had already visited Middle-earth and had become acquainted not only with the Sindarin Elves and others deeper in Middle-earth, but also with Men, is likely, but nothing is [> has yet been] said of this" - Peoples of Middle-earth

And then there is a possible meeting of Olorin with Galadriel in the 2nd Age concerning the "Elessar"

"...Olórin (who was known in Middle-earth as Mithrandir) brought it with him out of the West. And on a time Olórin came to Galadriel, who dwelt now under the trees of Greenwood the Great..... And when Olórin had told her many tidings she sighed, and said: ‘I grieve in Middle-earth, for leaves fall and flowers fade; and my heart yearns, remembering trees and grass that do not die. I would have these in my home.’ Then Olórin said: ‘Would you then have the Elessar?’ ....And he held before her the Elessar, and she looked on it and wondered. And Olórin said: ‘This I bring to you from Yavanna. Use it as you may, and for a while you shall make the land of your dwelling the fairest place in Middle-earth....' " -- Unfinished Tales