I printed a Disney calendar page on the Disney site for last April (the month we would have gone.) Then I got a small Mickey head paper punch, and punched enough Mickeys out of black paper for every day of the month until we were to leave. I ran the Mickeys through my Xyron to make them into stickers on a strip, and DS5 would put one Mickey on the calendar day each morning.
We had to cancel that trip, but I'm doing the same for our upcoming September trip.