I’m in the middle starting to plan our first trip back since my oldest’s MAW trip in 2012. We have 3 kids (12, 9 and 18 Months) We are trying to decide when to go. Our options are May 2019 the month before our middle turns 10 (the oldest will be 13 and the baby will be 28 months) or the week after Christmas thru New Years 2019/2020 which is the month before the baby turns 3 (older kids would be almost 14 and 10).
Pros of December trip, youngest is older and presumably a little easier to travel with plus still “free”. The weather will be better. We’ve been in February and March and felt that was ideal.
Pros of May trip, middle will still be 9 so not a Disney adult. It’s sooner
We won’t know the school calendar until spring 2019 so we won’t know for sure when school is back in session for January 2020 making it harder to plan December/January travel dates.
Extra info: I think we will plan 5-6 days at Disney Parks and 3-4 days at Universal Parks. My oldest is a huge HP fan and isn’t interested in Disney much. My middle has just started liking thrill rides and sadly isn’t into princesses anymore. The toddler? Who knows what he will be into by then but hopefully he’s a big Mouse fan. LOL!
Pros of December trip, youngest is older and presumably a little easier to travel with plus still “free”. The weather will be better. We’ve been in February and March and felt that was ideal.
Pros of May trip, middle will still be 9 so not a Disney adult. It’s sooner

Extra info: I think we will plan 5-6 days at Disney Parks and 3-4 days at Universal Parks. My oldest is a huge HP fan and isn’t interested in Disney much. My middle has just started liking thrill rides and sadly isn’t into princesses anymore. The toddler? Who knows what he will be into by then but hopefully he’s a big Mouse fan. LOL!