This year we took my then 19 month old and 4 year old to the first trip to Disneyland. We weren't sure what they would think about the rides and characters, but they LOVED it all. Yes, even the 19 month old. He was a little ride junkie. Whenever he wasn't on a ride he'd call out "Ry, ry, ry" asking excitedly for us all to go on another ride. We did 3 days in the parks at Disneyland, and I wish we could have done more. Going with them was wonderful!
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FYI Be careful of the water. One of the posters said that her nephew got the runs from excitement. It might be the water.
Not that it's bad, mind you, but that your child isn't used to it. Our DS got the runs and we realized it was the water we were mixing for his formula. We buy bottled water (at Publix if possible).
I also agree that going back to your room for a nap will chew up at least an hour in transportation (unless you're in a monorail hotel and even that will take time).
Stroller naps are your best bet. I have to say I absolutely LOVE the strollers at WDW. We had ds and 2 of his cousins (all 7 at the time) and it pushed like there was an infant in it.
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It's going to be really hot in mid-September, and since you'll be at VWL, getting to and from MK is super-easy. The boat ride is extremely relaxing and takes maybe 10 minutes. I think a break at lunchtime is absolutely worthwhile. I just got back from taking my adult children and three youngest grands. My daughter took the 3-1/2 year old back to VWL every day except one for his nap, and it was definitely the best thing for him. IMO, it's too hot from late May until at least the first of October to stay in the parks all day or have a child sleep in a hot stroller. I'd also skip the water park, but that's just me. I don't find there's that much to do for the little ones, and they enjoy the resort pools just fine.
I don't know how old your in-laws are, but as a grandparent, I can tell you that in the heat, I'm going to be out of the parks by 12:30-1:00 at the latest. There's a good chance I won't go back at all, but if I do, it will be after dark.
It's my understanding that a new Disney policy prohibits passengers from riding up front with the monorail driver.
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