When did the last of the High Elves leave Middle Earth ?

[Inziladun]

Originally Posted by Lindale

Inziladun, my reading of that Silm passage is this: What is the "then" Cirdan talks about? The last ship that will sail, or the return of Gandalf? I think it's the latter. Didn't Sam follow Frodo to Tol Eressea? So the "last ship" isn't the one Gandalf was in.

The 'last ship' could be taken to mean the one carrying Gandalf et al, the last voyage of the Noldor. Certainly he didn't mean to infer it was to be the final ship ever to leave the shores of Middle-earth.
'Then I will await thee' appears to say Círdan is waiting for the return of Gandalf to the Havens after the completion of his mission, which is when that ship was to set forth.