For the Castiel Club's secret santa this year (I forgot to do one earlier, sorry :S)
I love confused 'doesn't get it' Cas stuff, anything where he's literally a god damn puppy, over-running amounts of fluff. But like all Supernatural fans I have a dash of masochism and love really sad/depressing reminders of past events.
Traditional holiday things like decorating christmas trees, drinking egg nog, getting drunk and passing out on the sofa x-mas eve, trying to fight a war against over zealous sticky tape as you wrap presents - you know, the usual. I'd love to see Cas dealing with stuff like that.
As far as ships go I'm a fan of Cas/Crowley,