Would love some feedback on rainy weather in Orlando. Better to go to the parks in late August or early Sept?
There will be very little difference between those two times. Sept 1st is considered the peak of hurricane season. You can expect brutally hot and humid weather with a passing thunderstorm almost every afternoon. It’s impossible to predict when a tropical system may come through. I live in (NW) FL, and I basically refuse to go to WDW June-October.
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That is excellent feedback.
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How do you feel about the last week in May?
We are planning to go to Universal for 5 days. Probably taking afternoon breaks if its hot.
I do not do well in heat. We will have Express Passes though, so hopefully minimal outdoor waiting.
I was there over Memorial Day weekend one time and it was hot, but tolerable. I had a day trip in conjunction with a conference in later June, and it was too hot for me to really enjoy it.
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We were just there for the second week of September. It rained on us twice, both times for 10-15 mins. I came expecting to be drenched daily, and it never happened 
We have been in Jan, Dec and last year Sept. Planning a return trip this Sept, hopefully. It was hot but we planned for it and crowds were great, the lowest of any trip.
We were in WDW late August of last year. The rain wasn’t terrible. It only rained for about 10 -15 minutes, and only one day was an actual real downpour.
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There is no real difference between August and September as far as weather. On a 10 day trip in mid September it poured at least once a day. It was also insanely hot and humid. I have worked outside for 27 years, temperature very rarely gets to me, it did during this trip. The good news is it was the lightest crowds I’ve ever seen, and we still had a blast. Have a magical time
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We were at WDW in late Aug/early Sept. in 2017 and 2019 and you do obviously experience hot and humid weather…generally 88 to 93 for highs; it does rain every day or every other day; in 2017 there was a day over 95 degrees and in 2019 we had one day and one evening with a deluge of rain…the rest was the standard short rain periods that FL experiences…you plan accordingly with the rain but generally the crowds are lower during that time…in 2019 we also left a little early because of the hurricane
This will be our 5th trip in late Aug. Last year we left the day before the hurricane. It rains-but its quick and if it is longer than 10 minutes it does a great job of clearing out parks. We love grabbing a snack and waiting it out. One of my fave pics is of my son jumping in a puddle in an empty Fantasyland. The heat is worse than the rain!