Círdan probably the longest living elf in Middle-earth has been on Middle-earth since the days of the Two Trees and is the best ship builder of the Elves.
It is interesting that he never left for Valinor first when Morgoth was defeated in Beleriand, then when Sauron was defeated both in the Second and Third Ages.
Did he not want to leave Middle-earth because he's been there so long?
Did Círdan ever depart from Middle-earth or does he not wish to cross into the West and forever stay in Lindon?
Answer
All of the Eldar (the elves that originally travelled west Vanyar, Noldor, Teleri) left for the west at some point in the Fourth Age.
It is said that Celeborn went to dwell there after the departure of Galadriel; but there is no record of the day when at last he sought the Grey Havens, and with him went the last living memory of the Elder Days in Middle-earth.
The Lord of the Rings - Prologue
Cirdan was a Teleri elf so is counted as one of the Eldar. The above quote also indicates that Celeborn was the last of the Eldar to leave middle Earth.
I could assume Cirdan was on one of the last if not the last of the ships to sail west.
The following quote appears to back that up, with Círdan telling Mithrandir when he entrust him with the ring Narya.
But as for me, my heart is with the Sea, and I shall dwell by the grey shores, guarding the Havens till the last ship sails. Then I shall await thee.
The Silmarillion - Of the Rings of Power and the Third Age.
If Cirdan is still counted as a keeper of one of the three (much as former ring-bearers are always ring bearers) then the following would suggest he left before Elrond.
In that time the last of the Noldor set sail from the Havens and left Middle-earth for ever. And latest of all the Keepers of the Three Rings rode to the Sea, and Master Elrond took there the ship that Círdan had made ready... it passed into the Ancient West, and an end was come for the Eldar of story and of song.
The Silmarillion - Of the Rings of Power and the Third Age.
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