I just had customized t-shirts made up through the Disney Store.com -- they are currently on sale: kids $9.99, adults $12.99. I also made up a different one for each day. Since the trip is a surprise 5th b-day trip for my DD, one of the shirts says "Mary Pat's 5th Birthday Surprise Trip to Walt Disney World". The other's are variations of "our family trip to Walt Disney World/Feb. 2005".
Since you have certain things scheduled on particular days, I would reference the activity on those days shirts "[our family's] Grand Gathering, October 2004". How about black shirts with glow-in-the-dark letters for
MNSSHP? Then maybe do some park-specific shirts: i.e. an animal print for AK, with "[your family's name] on Safari in Animal Kingdom, October 2004"; maybe a shirt with a globe on it for your Epcot day.
Just so you know, if you order through Disney, you must spell out "Walt Disney World" fully; but if you order elsewhere, I would check with the merchant -- they not be willing to print "Disney" because of trademark/copywright laws. But trademark/ copywright violations usually only come into play when someone is making $$ off of someone else's material. Since the shirts are for your personal use, if you make them yourself, you should be okay.
Have fun!
