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  • Was Cirdan the Shipwright a better sailor than Earendil the Mariner? Doubt it. :)
    – Shamshiel
    Commented Oct 26, 2021 at 11:54
  • 1
    @Shamshiel given that Cirdan was, when he left, probably the oldest corporeal being ever to be in Middle Earth, I'm going to bet on him for being best at the stuff he did. Earendil was only ~30 years old when he left.
    – OrangeDog
    Commented Oct 26, 2021 at 13:25
  • 1
    The trip into the West was not one-way for the mariners who sailed the ships. For example, Gandalf and the other Istari got to Middle-Earth by ship. And this was in the Third Age, after the Downfall of Númenor.
    – Spencer
    Commented Oct 26, 2021 at 15:48
  • 2
    @Spencer there's no evidence that any Elves sailing from the Grey Havens ever returned. There's also no evidence of any Elves sailing from Valinor after the Downfall. You need some actual evidence that the Elves were operating a shuttle service, when the simpler solution is that Elves who wanted to leave simply sailed themselves, or waited for another Elf to sail with them.
    – OrangeDog
    Commented Oct 26, 2021 at 16:55
  • 3
    @Spencer I wasn't, but so what if I were? He was sent by the Valar - it makes perfect sense if Manwë gave him perfect winds or just told Ulmo to pull him across. Or Gandalf is simply capable of sailing a small craft by himself, if for some reason Manwë wasn't going to help his own messenger get where he was sent. And I have no idea what relevance you think Círdan giving him the ring has.
    – OrangeDog
    Commented Oct 26, 2021 at 18:23