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What if someone came to the shores of middle earth and built their own boat to sail on the sea? Could they reach the West where the elves have departed to?
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I would recommend that you read
The Book of Lost Tales I and II. The framework of the
Lost Tales involves a Man, Eriol or Ælfwine, that has found Tol Eressëa and is being told the "stories" of the Elves. Although the
Lost Tales are Tolkien's very early work and is not exactly what I would call "canon", they show the possibility of just what you ask.