Just back from our second trip, time to plan the 3rd 
I have taken my kids out of school the last couple of times but my oldest son will be in middle school next year so I don’t think I’ll be able to skip out on an entire week of school again (he’s having a hard time catching up from this years trip). I teach at college level and my breaks are never the same as my kids. So I’m left with 3 options; the week surrounding Memorial Day weekend, the last week in June, or the end of August. Which would you choose and why? We’ve only gone in October and the first week of February. Both trips were amazing in terms of crowds and weather. I need some insight into disney during my potential travel dates!
I’ve wondered how we will handle future trips when my kids are both in school!
Are there any long weekends where your time off coincides with your son’s? Maybe take advantage of those dates? You could still stay for an entire week but only be out of school for 2 or 3 days?
Of the three, the weather will certainly be the most tolerable around Memorial Day. And if you’re there at that time, if they have it this year, you could participate in the MK 24 hour day. The last week in August will probably have the lowest crowds of the three, but the weather will be like being in a sauna all day, every day. Late June will be the worst of both worlds; very hot/humid and larger crowds.
Even though I live in (NW) FL, I cannot do the mid-summer heat in Orlando, so for me it would be an easy choice - Memorial Day. I was there 2 years ago over Memorial Day; the weather was warm, but not unbearable, and the crowds were not bad either (not like Jan/Feb, but reasonable).
This is helpful, thank you! The heat would put a damper on things for us, my kids cant stand it! I wondered about the crowds over memorial week though. Thanks for the input!