When would you go if you were me

We like to go as soon as school lets out, which is before Memorial Day for us. There is no way I would go Christmas week with the crowds, but that is just me.
 
It seems you made up your mind already but I'll vote for xmas time too. I can't deal with heat AND crowds. But I think I work better with crowds. I have been to Orlando too many times in the heat where I've been too hot to even take out my phone for pictures. I just wanted to get in a/c.

Have you thought about Disneyland in California? It can get crowded but the weather is beautiful.
California is a very expensive flight from Toronto. A bit too much for the budget right now! One day!!!!
We like to go as soon as school lets out, which is before Memorial Day for us. There is no way I would go Christmas week with the crowds, but that is just me.
Our last day is June 30. It's a late one here.
 
Given that you're from Canada, I'd definitely choose Christmas over summer. FL summer days can be unbearable at times, and this is from someone who lived there for over 10 years. Have fun!
 
I am a teacher too! This year we are going the week after school gets out in June, and have before. We have gone during spring break and the crowds were crazy! We also used to live in FL so we have been several different times of the year for shorter visits.
One year, which was my favorite, I used both my personal days and went just for four nights the last week in September. It was, by far, the best time of year I have gone (while not living in FL).
 

We're also a teacher family. We've done six summer trips to WDW and are planning this summer as well - middle of August. We strongly prefer a long trip, ten days if possible, which lets us break from the heat mid afternoon if it is horrible; somedays it is, but not all of them. AK always seems to be the hottest park, mostly because there aren't as many indoor spaces for respite. Seeing Disney at Christmas is on my bucket list, but I'll never be able to do a long trip at that time of year. Some summers are HOT, but crowds and costs are lower in August than Christmas.
 
Here is another vote for Christmas. We went a couple years ago -- arriving on NYE - so still crazy Christmas season. It was busy, but if you adjust your expectations, plan ahead all dining, take advantage of EMH and being at the park for RD, then you can still have a great time. If you have never seen the parks decorated for this time of year or the castle draped in icicles then you have to go at Christmas. It gives me chills just thinking about it. Despite the crowds -- the weather will make it a much more enjoyable visit. Try and go for as long as possible so that you don't have to be park commandos to see everything.
 
Now that I see that you live north of Toronto, you should also consider the impact that winter weather will have on travel at Christmas and plan for any delays that might cause.
 
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I would love some input as I am having serious second thoughts about my planned WDW trip.

1. I am a teacher so cannot go during the school year (not complaining love my job)
2. My daughter plays rep hockey so spring break always falls during playoffs (she can't miss)

That leaves Christmas (a lul time for us in hockey world) or summer.

My plan was Christmas but it is scary to read about the craziness. Summer is also crazy, plus hot, hot hot!

I appreciate any advice/insight

What's your school calendar like? Depending on the part of the country, there's going to be some overlap, where you're done, but others are still in school. If you're a more traditional start after LD and get out in June, I'd def. go as close to the end of Aug. as possible. If you start in Aug. and get out in May, then I'd go as soon as possible once you're out of school. Yes, it'll still be busier than the beginning of Sept. or slow times during the rest of the year, but it won't be as bad as regular summer crowds and def. not as bad as Christmas.
 














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