Dd is in first grade, but we are doing a few things both before and during our trip:
Dd has compared both her height and ds' height from their growth chart, with the ride height requirements for WDW rides. We have a list of what dd cannot go on, and a list of what ds CAN go on.
We made a link chain to mark off the days until our trip. Dd counted the links up to 100 and predicted the pattern for each link (red, white, black). This also gives her a concrete amount of objects up to 100 which she can see and help her estimate how much longer we have left until our trip.
Dd has already done some map reading. We used the Passporter maps as well as the free Disney ones. She identified different symbols from the key and then figured out where we would get on/off the bus, where the bathrooms are, parade routes, monorail routes and which buildings are restaurants, rides, etc.
Dd is "earning" Disney Dollars for our trip. She keeps them in a wallet and takes them out to count periodically! This is her money to spend during our trip. We will try and guide her, but she will need to figure out what to spend it on and make decisions accordingly.
Dd will keep a journal while we are there. I was going to make one but found Guide to the Magic for Kids instead. It has all kinds of places for her to write short sentences about our trip as well as stickers and other info. The Epcot section has places for her to get her passport stamps as well so we may not have to purchase one! Instead of your kindergartener keeping the journal... you could ask him the questions and record his answers!
Dd will also have her camera so we will help her put together a slide show of images for her to share w/ her class after we return.
I'm going to talk to her teacher at Back to School night as to exactly what steps we need to take to have dd excused. I'm going to show her Beth's journal and explain all she's ALREADY done to prepare for the trip at our parent/teacher conference in November.