Who steered the Grey Ships into the West?

Question

The journey into the West by Elves leaving Middle-Earth was a one-way trip. Not a shuttle service.

That would imply that any nautical crews on the ships also weren't coming back.

However, floating the boats isn't a task for amateurs: you'd need to make sure that any trip had properly trained crews.

I had this silly image in my head where things go something like this:

Elrond: Avast, ye landlubbers!

Galadriel: ... what?

Elrond: Just lightening the mood. We're outta this here sad and sorry lands. Next stop: Tol Eressea. Now, everybody call me captain!

Gandalf: I've got your "captain" right here, boyo! Now, who knows how to steer one of these things? Cirdan gave me a ring, not a Boating for Dummies book.

Galadriel: Is this thing supposed to be taking on water?

Elrond: No idea, but we can always throw one of the hobbits overboard. They're really just ballast.

Bilbo and Frodo: ...

Seriously now:

Who steered/crewed the Grey Ships and where did the crews come from seeing as it was, by definition, an attrition process?

Were they "magical", imbued with some pathfinding auto-pilot by Cirdan? Then, how did Legolas' ship work? He was a landlubber, from Mirkwood.

Did Cirdan keep training crews among those who had decided to leave, with just enough minimal personnel to get them safely into the West?

Was it just one of those "Elves instinctively know bloody everything"?

Answer 1

Reading the Silmarillion gives the impression that a lot (almost all) elves eventually spent some time on ships - either when the sons of Feanor returned from the West, or up and down the coast and around Belfalas.

It's also possible that the Valar simply take control and help the ship cross over - as we see Ulmo do at various times (including the crossing of Glorfindel).

Answer 2

While most Elves were heading west at the end of the Third Age, there is nothing to stop a few going in the opposite direction. It is likely that there had been sailors going back and forth between the Grey Havens and the West since the start of the Second Age.

Keep in mind that Gandalf and the rest of the Istari arrived by ship at the Grey Havens from the West.

Answer 3

Most of the Elves living at the Grey Havens, and most of the Elves in Middle Earth in general, were Teleri.

The greatest host came last, and they are named the Teleri, for they tarried on the road, and were not wholly of a mind to pass from the dusk to the light of Valinor. In water they had great delight, and those that came at last to the western shores were enamoured of the sea. The Sea-elves therefore they became in the land of Aman, the Falmari, for they made music beside the breaking waves.

^{― Quenta Silmarillion, "Of the Coming of the Elves and the Captivity of Melkor"}

They were especially noted for being expert mariners, and none of them would have any trouble steering ships to Valinor. They didn't all leave at once, but gradually, so there were always someone available if some land-lubber Noldo turned up. Legolas and Gimli sailed there in a ship he built himself ("it is said"), so you don't need lots of people.

Círdan in particular, who ruled the Havens and made sure he was the last to leave, was possibly the greatest sailor ever known.

The Noldor weren't incompetent sailors either, half of them having gotten back to Middle Earth by boat in the first place, and the other half only walked the long way round because the first half burned all the remaining ships. Though arguably that was before you had to find the Straight Road.

So in short, most Elves were skilled sailors. Being skilled at everything (due to their long lives) being one of the primary Elven traits.