I'm in your boat as well! (and in your city - Winnipeg!) Due to my fiance's mom being a teacher and our various siblings being in university, Christmas break seems like the only time everyone can go.
We had our hearts set on Cuba for a long time, but now after the chilly winter they had this year, we're considering other options as well. I don't know what to do either. Cuba appeals the most to me (I've been there once in January, and the weather was really nice, although it rained for 2-3 days.)
Have you decided what you're doing yet? Also do you have a travel agent yet?