I've only been teaching 11 years, so I haven't been brave enough to try a vacation when school is in! Also, for 9 of those years I taught Pre-Kindergarten, and the class falls apart if I'm not there for one day, much less 5! I now teach 2nd, and it would still be very difficult to go on vacation during a regular schedule. We have been once in summer, twice on our Spring Break which is always before or after Easter (and also near my son's bday), and now once at Christmas. We liked our summer trip best, so we'll be doing that again in 2006. Where I teach in Texas, we get out right before Memorial Day, so get a chance to go in early June before most vacations begin (and also near my other son's bday.......yep, I got ZERO leave with him because he was born in early summer!). We've never yet had trouble with crowds at any of those times..........the first time we went was summer and we were clueless and there was no fastpass.....but because we were clueless we didn't know we shouldn't have to wait so long. Ever since, we've used fastpass, early entry, leaving in early afternoon, late nights, and park hopping and had no troubles.