As for why Gandalf went with Frodo and Bilbo in the end, I personally think all the ring bearers went on that ship. Galadriel, Elrond went, and didn't Cirdan go too? I'm not sure about that.
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'It must often be so, Sam, when things are in danger: someone has to give them up, lose them, so that others may keep them' ~Frodo
"Life is hard. After all, it kills you." - Katharine Hepburn
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