Two Questions about Gandalf in the Undying Lands
 

Before I go any further I am well aware these are more along the lines of speculative rather than factual questions, since I don't think that Tolkein wrote much of the more intimate details of the Fellowships post-grey havens lives. And indeed the day to day affiairs of the people of Aman may be "beyond mortal ken". But I think these may at least provoke a little discussion.

1. If I recall part of the deal with the mortal sailors is that, while they are allowed to be in Tol Eressea, they are not allowed to go to Valinor proper. But this stricture would not apply to Gandalf himself. So my question is as follows; once the boat got to Tol Erresea, do you think Gandalf stayed around there for a while (defined as "until Bilbo, Frodo, Sam and Gimi died) or did he immediately head off for Aman itself. On one hand, he might stick around so that the hobbits and gimli wold have some familar faces around. After all Frodo and Co. dont reallty know a lot of the other people there. They know Elrond, they know Galdriel and that's really it (unless Bilbo in his sojurnment in Rivendell got to be on friendly terms with some of the members of Elrond's court who either sailed before or with (I still maintain that Elrond, Gadriel, Gandalf and two hobbits is a rather small crew to sail a grey havens boat (especially as neither hobbit probably knows much of sailing) (Yes, Legolas manages with a crew of two, but he built his boat so he probably bult a smaller one than an official "grey havens special" so I think they may have been other elves on the boat of lesser importance (members of Elronds, Galdriels and Cirdan's courts also making the journey) to do the actual crew work. I'm sure Tol Erresea is wodnerful, but I can easily imagine the hobbits feeling a little alienated without familar faces around, and Gandalf might very well, decide to stick around to keep them company.
On the other hand, Gandalf is a Maiar, and as such Valinor is his home, not Tol Erresea. I Imagine he misses his friends back there (the unfinished tales say Alatar took Pallando as a friend on the trip there, so it is obvios that Maiar do form attachments between each other.) He may miss his home in Manwe's gardens and seeing Irmo and Nienna. He may want some insight into what happened to Alatar and Pallando (assuming the Valar know) or on what the Valar plan to do with Radagast (leave him be as is in ME? Take away his immortality and let him die? give him a second chance to make it back?) I suppose this isn't really an either/or choice (Gandalf go stay in one place and visit the other frequently) but it is worth consideration.

2. Once he gets to the Undying lands, does Gandalf stay....well....Gandalf. The Unfished Tales say the Ishatri came to Middle Earth in the guise of old men, which seems to indicate that that is not their default appearance (I know maiar can shapeshif in thier non-incarnate state, but the meetings between them and the rest of the people seem to indicate that most have some body form that is a preferred "default" one. Presumaby, now that Gandalfs mission is over, and he is no longer under the strictures of the mission, he is no longer obligated to keep that form. So do you think he does. I can sort of imagine him keeping it as long as Frodo and Bilbo are around, for the same reason I stated above for him possibly sticking around Tol Erresea, so they have something familar. But has Gandalf gotten so used to being Gandalf that that is how he will stay, or will he turn back into whatever he looked like when he was Olorin?

I don't see an issue with Gandalf traveling back and forth from Aman to Eressëa as he pleased. As you note, Gandalf was in a different category than any other of the ship's passengers, and he could presumably keep the hobbits and Gimli company as long as their natural lives endured.

I think you're right. The reader isn't told the total number on board the ship, and I always for the idea that Elrond, Gandalf, et. al, were not required or expected to contribute to the actual sailing tasks.

Well, we are told in The Silmarillion that the Valar and Maia were capable of presenting themselves in any form, or in no perceivable form, at all. The difference with the Istari in Middle-earth was that they were bound to permanently inhabit those bodies while there. After Gandalf's return to the West, he should have no longer been subject to that rule.

Wind
 

I've always presumed that Radagast -- along with Bombadil, Goldberry, Shelob and other odd beings of great power -- were left alone.

I'll note that in Saruman's case, a shape of mist formed over the body, looked west, but was dismissed with a cold wind. I think this left Saruman, like Sauron, as a spirit of malice unable to take shape again. I'd like to think Radagast would be accepted, that should he die he would be allowed to return over the seas and take another shape. He might not have been as aggressive as Gandalf in fighting Sauron, but he was no traitor.

No one is sure where to tuck Bombadil and Goldberry, but I wouldn't be shocked if they had that option too, or if they just continued to dance and sing though the Fourth Age.

But we don't know.

I can accept that fate for all of them, except possibly Shelob, who, unlike all of the others, represents a very real, palpable danger to people (I had always assumed that, as part of any attempts to "restore" Mordor somebody (If not Aragorn himself, then possibly Eldarion or if they reached sufficent might, the people of Nurn) might (as soon as they were no longer needed for more pressing restorative matters) have sent a large consort of very well trained, very well armored, very well equipped with lights knighs specifcally to track down and slay Shelob, and so clear the Cirith Ungol Pass (leaving it as is not only means leaving Shelob free to potenially prowl munching on travelers (with no orc sacrafices to feed her, hunger might lead her to leave her lair to hunt at night) but a back door open for anyone to pass in (Mordors secutrity problems remain the same no matter who is actually in power))

Spider Hunt
 

A Shelob hunt would be a pure noble and appropriate task. Very glorious.

Alas, I'm not feeling any great need for additional glory. I'll let you handle that one.

I imagine Gandalf would change his form into a younger more energetic form. He loved hobbits, and it wouldn't suprise me if he took the form of a hobbit, just like Aule did when he settled in the old forest.
Radagast was probably allowed back, Bombadil and Tom are most likely Valar and so they could do as they pleased. Shelob was just a spider...xD

I don't know that I buy Bombadil as Aulë, but that's another thread.

It seems to me much more likely that Gandalf would have appeared, to the hobbits at least, just as he did in Middle-earth.
If he indeed, as I think, wasn't bound to any particular form and could change at will, why not keep on the "clothing" with which his friends were familiar?

I haven't the time for searching at the moment, but I recall a very good thread here about the fate of Radagast in the not too distant past. If I think of it later, I'll edit it in here.
Basically, Radagast, to my mind, failed in his primary task, since it was said the ultimate mission of the Istari was to rally Middle-earth against Sauron. Radagast instead got caught up in flora and fauna. He was probably allowed back to the West eventually (if he even wanted to return, that is).

It sort of depends on how "accurate" the clothing was. In other words, did Gandalf in his Middle earth guise merely look like an old man, or since it was an incarnate body, would he also feel like an old man. It is mentioned that the only thing that aged the Ishtari was the rigors of their labors, but Gandalf's labors were pretty rigorus (not to mention that, if the UT tales chapter is taken as canon, Gandalf came in a form much older than any of the other Istari right off the bat. They all have staffs, but Gandalf is the only one specifcally described as NEEDING one to get around.) If the latter, I can imagine Gandalf, once he was permitted to do so, might very well at least take on the form of a somewhat younger man; one free of whatever aches and pains the age of his "Greycloak" incarnation plauged him with. He could still look enough like his old self to be recognizable to his friends as Gandalf, just a healthier, fitter, more nimble Gandalf.

If I'd be Gandalf I would take the form of a young woman. Like after having spent some thousand years as an old man it would be nice to try something different. :D

Well, in Middle-earth Gandalf was given that particular body for a reason, I think.
Even though his spirit, as divined by Círdan. was the "greatest", his physical embodiment was the weakest-appearing. Perhaps the purpose of that was to reinforce his humility, with a side-effect of reducing his chances of being able to intimidate weaker beings by his looks.
In the west though, he would no longer have been "trapped" in that body, and could therefore have had any body he chose without it affecting how he felt physically.

Tolkien sadly never said what happened after they arrived in Aman, but I like to imagine that they had a first stop at Tol Eressea (cause the Hobbits can´t enter Valinor, so they had to stay on Eressea I think) and that there were solemnities to honour the ringbeareas for their work against Sauron and all important people of Valinor attended, maybe even some Valar. Then, after a few days the elves would continue to Valinor itself (the hobbits of curse would have gotten a nice home) and there I think Gandalf would change his appeariance.

The fate of Radagast is interesting and can be argued either way. But since Saruman, even after Wormy whacked him, tried to seek the West you'd think Radagast would be admitted back in Aman---if he wanted to.