July ... Or October and HHN?

I wasn't tracking on Disney World's 50th anniversary; to me, that will suck up a lot of the oxygen, especially since it seems likely that Disney could be at 100% capacity that month. But since I've only been to Orlando once, that's just a guess on my part. June isn't really an option; my son has a couple of camps that month. If anything, earlier in July would seem more in play TBH. But we're also considering Volcano Bay as part of this trip, and those are generally blacked out in July.

My expectation is that school kids only have a few days in October available, and that will tend to keep crowds smaller than in July...but I know some parents are more than willing to pull their kids from school for a vacation.

We're not into haunted houses, though my kids enjoy the pumpkin patches. It's not that we hate haunted houses...it's more that it doesn't interest us. I figure there's plenty of things to do that we can just pass that stuff by.

As for the July cruise that was just cancelled...we didn't really expect to go on this one, but put in a reservation anyway knowing that if things suddenly turned around this spring, we'd be set. And if didn't, we'd go to our next option. (Actually I didn't expect our spring break 2021 cruise to happen either when I booked it in March 2020...but again, put your name down and hope for the best.)

I'm tempted to stick with October at this point... I get your point about hotels and Disney being crushed, but airfares look much more reasonable in October than July. That's signalling that October might be preferable. (No annual pass rates for October for me to sort this out...)
 
If your trip will be October, book the hotel room
now

If you change your plans later, cancel the hotel reservation

Hotel rates will increase when less rooms are available.

I booked my onsite hotel at UO last September as rates were low and rooms were plentiful for the trip that’s a year out.
 
October is also hurricane season. Having said that, we are already booked for our HHN trip this year. We've been going to HHN for about 10 years, and only one year personally affected us (on our departure date, thankfully), but a couple of years had big storms before our arrival that didn't affect our dates. Just wanted to throw that out there for your consideration.
 
July is also hurricane season... This table shows tropical cyclones (so that's depressions through hurricanes) hitting Florida since 2000.

MonthNumber of Florida tropical cyclones
April1
May6
June10
July11
August23
September31
October14
November5
December1
 

I agree with PPs that this October is likely to be busier than a "normal" October due to HHN's 30th anniversary, and the fact there was no HHN last year. October also starts WDW's 50th anniversary festivities and I have to think some folks attending that will combine it with a Universal trip as well - we will be.

That said, if you can stay on-site with express pass, I would pick October over July. July is also busy and the heat, humidity, and chance for rain/hurricane can really put a damper on things. Even though its busy in October, the weather makes it much more tolerable. Do keep in mind that Universal will close around 5pm on days with HHN. IOA will be open later to compensate, but it does make it busier. If it were us, we'd reserve the evenings for City Walk or the pool and avoid the parks after 5pm.
 
Just for the sake of giggles, I was looking at hotels during that week, but Hard Rock Hotel wouldn't show up unless I changed my dates to exclude Friday and Saturday night. So that leads to the conclusion that the Hard Rock might be currently sold out on that weekend.
 












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