Quote:
Originally Posted by The Mouth of Sauron
It's by no meams certain that Legolas and Gimli left via the Grey Havens. Rather Legolas "built a ship in Ithilien" and therefore probably sailed west via the Anduin.
Also I'm not sure that the Grey Havens were simply ports. Even in the Fourth Age there were still High Elves left in Eriador and it's possible that they used these Havens as a place to live.
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I've also wondered if the Grey Haven's might have been a sort of "way station". Based on the description, most of the regualar boats were crafts of at least reasonable size, and so would need a decent size crew* (maybe 10 or so, or double that if elves tire and need to work in shifts). Since all trips from the Grey Havens are essentially one way, that means that each trip needs about a dozen people. Unless elves tend to get the call en-masse, or form alliances where the weary agree to wait until fellow elves get weary before they leave, this would mean that every now and then, an elf might need somewhere to wait till there was a sufficent party for a voyage (this seems not to have happened in the case of the Fellowship, but by that time elves were leaving fairly frequently, so finding five to seven others might not be hard.) The Grey havens might be there for just that purpose, an Elven community that, amongst other things, houses waiting elves until their turn comes up.
* Legolas in all probabilty did not take anyone except Gimli with him, but Legolas built his own boat, and presumably bult a smaller one, that only needed a crew of 2 (or 1 to allow him and Gimli to share the work) Even so, I imagine that, in terms of sheer labor, Legolas and Gimli had a somewhat more arduous and strenuous trip than most to the Grey Havens.