If it is the second, I wonder how long Cirdan would have lingered: there would have to be some limit - he's been waiting a long time! He wouldn't wait for all the elves to overcome their sea-reluctance and we know some tarried, perhaps to this very day: "as by men of later days Elves still at times are seen: present and yet remote, a living vision of that which has already been left behind by the flowing streams of Time."
The passengers that traveled with the Three Rings seem a select group: all linked to the Rings. Gandalf, Elrond, Galadriel, Bilbo and Frodo. Bilbo and Frodo and both borne the One, so the fact that Cirdan had yielded his Ring to Gandalf doesn't rule him out.
There were Ringless companions, Gildor and Co. I don't think Glorfindel sailed with them, he'd be mentioned, but I can't see him being excluded from an eventual return voyage.
I wonder about the other high elves left behind. Arwen's fate is set, but what of her brothers? They do linger after that voyage, but are not paired off with any mortals. Does Elrond's words about Arwen apply to all his children: "I should still be grieved because of the doom that is laid on us...that so long as I abide here, she shall live with the youth of the Eldar...and when I depart, she shall go with me, if she so chooses." No later trip. Yet we hear nothing of a grievous parting of Elrond and his sons. True, fathers may be partial to daughters, but I still get the idea that Elladan and Elrohir will take a later ship.
Then there's Celeborn. His parting words to Aragorn beg some explanation: "Kinsman, farewell! May your doom be other than mine, and your treasure remain with you to the end!" Celeborn seems fated to be sundered from Galadriel, and his words have an air of permanence which make it questionable that he will catch a later ship when he tires of East Lorien and Imladris, where he dwells for a time with the sons of Elrond.
I don't know what conclusions to draw from this: the evidence seems contradictory. Any ideas?