We currently are booked to thru Dreams to WDW in late August/early Sept for a week. However, we are in Canada and things haven't opened up to a point where we can travel without 14 day quarantine, so I'm going to have to cancel (again....second time cancelling!). Our kids are currently 5 and 7, so young enough that I don't mind if they miss school. They've been to DL but not to WDW, and so we are more attraction driven and aren't too fussed about festivals etc. What time of year would be the BEST time to go, for crowds to not be too busy? I don't mind taking them out of school for a week, but would really like to not go at a time with massive crowds. Our school breaks in Canada don't always line up with when they are in the US, so I'm not totally certain when the peak times of year are down there. Thank you!!
So we've been most every month other than September, Oct and December. While it used to be back in the day summer was peak and that's just not the case anymore. There are really crowded times, like pre-covid shoulder to shoulder and you can't hardly walk times, even a few where they close the park to new guests for some times though-out the day. Those days are rare but they do happen. The crazy crowded times may be back or may not be, it's anyone's guess what will happen with park pass but I guess it's around until at least fall of 2022. I think the days of predicting crowds are now a bit harder and I also feel like being in the parks since Covid, the crowded feeling is definitely there even though it's really not crowded. So a really popular attraction may only have a 15 min wait, but the park can feel like everything is swamped. I hope by the anniversary, that most if not all, entertainment and shows are brought back so this will alleviate this issue.
If you can pick any time that works for your family, I would steer clear of June-September just given the weather. I'm not from Canada but I would imagine, the heat and humidity alone would be a deal breaker, let alone a hurricane. Throw in August/September peak hurricane season time, and I'm going to say you should pass since you are traveling from so far away. We are a few hours away so it's easy enough to change plans so we don't mind going that time of year but if I had to book tix, that would be a hard pass for me. Even though most hurricanes are a non-issue in central FL, it still can wreak havoc on air travel. We usually go early June and early August because of lower crowds and even our trip last August, Hurricane Isaias was off the coast and may or may not affected air travel but we just drove down a day early to avoid the rain.
The other times I'd be cautious of are American spring breaks (March/April), Thanksgiving and Christmas. The spring break season is a tough one since school breaks vary but usually the the week leading up to Easter is the busiest and the weeks where Osceola/Orange and other surrounding counties (locals) have break is also fairly busy. We really like visiting mid November after Jersey week (some teacher convention in NJ that for whatever reason, most of the New Jersey folks infiltrate WDW, IDK, it's a thing LOL) and it is def more crowded in early November because of it. But mid Nov before Thanksgiving are busy but not insane and it's typically great weather, cooler, not as humid and not rainy. Also, at this time, most of the Christmas decorations are up. We last visited this time back Nov. 14-19, 2018 and it was wonderful but we've not been able to pull our kids out of school since as they're older. We could swim, we enjoyed all the holiday treats, did a
MVMCP and more. It was one of our favorite visits.
Another great time we like to visit is Jan/Feb. It will be more crowded closer to President's day but there is a lull mid January up until the holiday. Later April and most of May is also a nice time, it's hotter than most would like and can be rainy but it's usually not crazy crowds. October has gotten to be a fairly busier month too even though it is usually still pretty hot. I've never been the first week of December but that's also known to be a sweet spot for lower crowds, relatively speaking, than Thanksgiving and Christmas.
If I can go anytime with no regard to schedules, I'd pick January/early February or mid November. Both times have nice weather. If swimming is super important, you could also look at late April/May. I know the pools are always open all year and yes they are heated. We don't usually swim since it's too chilly for us but I suppose it's relative. Our kids are a little older so swimming is not super important to them but even in cooler weather, they'd usually swim and we'd sit that out.