This will be our 2nd 4 day cruise....so I am new to the
Castaway Club also. Like you, we only received a letter

I even called and asked for the CD. They said that they would send one....that was 2 months ago. AS far as a get together

the way I understand it is that there is a Captain's reception that only Castaway Club members are invited to. On these boards I have noticed that fellow DIS board members have set specific places and times to meet on another. I think that would be FUN!!!
We DO NOT have passports, since we have never been "forced" to have them. I just could not justify spending the money...especially since we have had no problems so far. BUT next year will be a different story.
We did sail around the same time last year. My kids last day of school is always the first week of June. We found June to be perfect weather, seas, etc. YES, there were crowds at Disney, but with a little planning and fast pass we were able to do everything we wanted to.