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We have "surprised" our kids mulitple times. That being said, our original surprise setup was my favorite. It involved a scavenger hunt with clues containing subtle Disney references. The last clue took them to a decorated custom cookie in the shape of Mickey's head that the local bakery made for us. We go one to two times a year. The only surprise left is when we will go, the meals, and any special tours or activities I have planned.
We've done the surprise multiple times as well. Once we mailed a Disney postcard to our house addressed to the girls ftom Mickey telling them he would see yhem on Sunday. Here it is:
I left a Red envelop from Santa on the tree with the trip documents in it one year. After everything was opened my DW, playing along said, "what's this, did Santa leave another present?" When my DS opened it he knew what it was and started yelling.
Wrap up their suitcases in wrapping papeer all packed and ready to go? My mom did something like this years ago! I have to say I was a little confused but I got the point. I hope someday I can do this. What a great gift