Free water park day worth it?

For those who fly in it’s not as simple due to transportation, booking a different accommodation, etc.

Personally, if we landed at 11PM the first thing I’d want to do is get into Disney property to start my vacation.

Yup. Last trip we landed after 9 pm. Staying offsite wasn't even an option. I like to unpack and start my vacation. I don't even like split stays because of the unpacking/packing situation.
 
My wife and I are in the same boat and while I'm not sure if it's an option for you we found red eyeing the night before has been the best way for doing it.

I was lucky to make it 3 times last year (meeting family twice and then my wife and I's yearly trip) and all three times I red eye'd. Let me arrive sooner then my east coast family so I could check myself in and then go off and get food/do what I(we) wanted.

We are doing the same thing in August and I'm planning our first day at the water parks because we will be here so early. drop our bags off then head over to the waterpark first thing to get in. We haven't been able to make it to the water parks yet so I'm aiming to do it this trip if not once maybe twice just to do both.
I generally hate the red-eye - we end up bleary-eyed, fighting with each other and unable to get the needed rest because the room isn't ready until the afternoon. Being able to go the waterpark is a great option because, at the very least, you can kick back in a beach chair and get some sleep.
 













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