Sam's final journey

[Guinevere]

originally posted by Formendacil
He also says that once the Ring is given up, the Ringbearer would just pick up where he left off (my words, and interpretation).
I've always taken that passage to mean that Bilbo, once he gave the Ring, was essentially still a 50 year-old hobbit.

Quite right. But what happened after the One Ring was destroyed ? I think that then, the real age of the person would show!
Arwen told Frodo about Bilbo:

For you know the power of that thing which is now destroyed; and all that was done by that power is now passing away. But your kinsman possessed this thing longer than you. He is ancient in years now, according to his kind."

I wonder what would have happened with Gollum after the destruction of the Ring, if he hadn't fallen in the lava with it.. Would he perhaps have crumbled to dust?

Back to topic! (Sam). Tolkien states in his letter (about mortals in Aman)

and they would eventually pass away (die at their own desire and of free will)

If they die "at their own desire and of free will" (like Aragorn and the old kings of Númenor) then Frodo surely would wait for Sam to join him! After all, he had, at his departure, told Sam "your time may come".