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Interesting point Essex. You said the following:
"And I like the idea that it's a 'tradition' that Sam followed Frodo 60 years later. Did he actually get to the undying lands? did he meet Frodo? was frodo dead already? Was Sam actually allowed to follow him, or did he spend the rest of his years looking out over the gulf of Lune and die peacefully at the Havens?"
May I point out that in "The Letters of Tolkein" he informed one inquirer that Frodo would never be able to come back to Middle Earth, that once he set foot in Elvenhome, he was bound to stay there. And no, Frodo was not dead yet. "The Letters of Tolkein" is a treasure trove of additional information dealing with many of the characters and the choices they made. Tolkein indicated that Frodo lived a very long time in Elvenhome (for some reason the number 300 years comes to my mind), but that eventually he did die, as did Bilbo.
However, Gandalf, being a servant of the Valar, would have been able to come back to Middle Earth. He and the other Ishtari, including Saruman, had been sent by the Valar to Middle Earth when the Men of Numenor were washed upon it's shores. They were guardians then, they are guardians still. Gandalf could go where the Valar sent him.
I also think it interesting that none of the hobbits of the story died in the Shire. Merry and Pippen died in Gondor, Frodo and Bilbo went overseas. Sam was never heard from again.
I want to think like Elenor - he went overseas.
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