Also just to chime in—- I LOVED my trip with my then 2 year old. Sure we managed expectations, but I love that I have those memories.
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My kids were well behaved. I was trying not to say my bf lets her monsters do whatever they want so I don’t think she’s the best person to take advice from 
and I don’t know anyone else that’s been to DW with toddlers. I don’t know many people with toddlers period.
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Nothing little man does frustrates me. I’m pretty patient and not pushy. If DGS gets fussy, we reroute to quite spaces. I have a list of places. I get like 4 hours every other Saturday to sit down and plan without interruption so it takes me a while.
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This might give you ideas… I’m trying to find another thread that talked about places a toddler could safely let off energy.
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That’s why I threw all this out there. I welcome all advice. I’d like to plan realistically now and can add if it’s seems right but I’d hate to have to take things away bc I went a bit bonkers with adding in too much. My kids didn’t nap much. DS was done naps altogether by 2. DD needed quiet, DS could sleep standing up.
We did a 9 night trip in 2018 with my son when he was 2y8m. We only survived with a happy toddler and therefore a happy family by going back to the room for naps (he was never a kid that could nap on the go). I would definitely minimize the days that you don’t have a home base, and anything you can do to maximize the convenience travelling to the resort is helpful! Resorts with skyliner, monorail, and/or walking options would be amazing. Also, I would suggest a resort with an elevator. We stayed at Port Orleans Riverside and lucked out with a ground floor room, but as soon as we got there I realized the challenges if we had ended up with a second floor room.
We also kept to bedtime. We only had one late night where we booked the fireworks dessert party - with a toddler we wanted the snacks and a less crowded area without camping out to watch the show! We also did it the last night - we didn’t want to be dealing with an overtired and cranky 2 year old from the beginning of the trip and struggling to catch up on sleep. Especially with a longer trip, we definitely planned on taking it slow.
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I have done four trips with a 2yo or near 2yo over the last 3.5 years.
I’ll echo what’s already been said: get rid of the split stays (or at least one of them. I know it seems like park accessibility sounds good in theory but the disruption to routine and having to pack up a toddler’s things that many times in a week is going to cause more stress.
When mine were that little, we’d plan to do AK without a break - we’d get there for rope drop and be out of the park by 2pm. One of mine fell asleep in the stroller easily enough. The other was cranky for missing a nap but rested in the way back to the hotel.
The other park days, without question, there was a three hour break in the middle of the day. I personally chose Contemporary for two of these trips as the walkability to MK (and park hoppers) was supremely helpful to me. The kids didn’t/couldn’t do much at HS at that age, so it was MK and Ep for the most part, so the MK properties won out. But your GS may be different.
My younger one also napped on the monorail for a good hour last year while we looped and his big sister rode the teacups with her dad about a dozen times in a row. So you don’t always have to go back to the room - as you and others have said you won’t know until closer to the time.
But I’d err on the side of planning for purposeful breaks and if your GS is the kind who can and will nap on the go, you have extra time in your days then. If not, you’re ready.
The other thing I’d caution you about is planning for evening events. My kids both needed to be in quiet/wind down time by 7 or 7:30 even with breaks/naps. (But they were up at 6am) Again, you won’t know until closer to the time and can adjust accordingly, but I’d start your plans with the expectation of FAR shorter days than tire probably used to.
My other piece of unsolicited advice is to consider a villa - having the kitchen and laundry for a toddler has been great. We obviously did fine at CR without, but those were both three day trips. I would never do a week with a two year old without access to a full refrigerator, toaster oven, microwave, and laundry….
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One thing I noticed on our trip 2 weeks ago, when baby is tired, if he won’t nap in the stroller (mine wouldn’t), please, please, take him for a nap! We were behind a family in a long (45-min) line for a ride, and they had one that I’m guessing was 3 and one that was around 2. Both kids were crying and fussy, and the older one was begging to “just go to my bed”. (Not saying you would do this, by your post, I’m pretty sure you wouldn’t. Just sayin’). We saw so many little ones who were cranky and crying and looked like they needed a nap. I felt bad for them and thankful that my kids are grown!
When mine were little, way back in our early WDW days, we would do park opening until around 12:30, go back to the resort (always a value then), take a nap, and then park hop for dinner and after until the kids were tired. We did a lot of pre-park opening character meals, but I don’t know if those exist right now and who knows what will be when your trip happens. It was a good way to meet the characters without having to stand in line.
When mine were that little, they didn’t really care what park we were at, they were thrilled with all of it. We spent SO much time playing in those fountains that squirted out of the ground, they just loved it.
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Forgot to add I’m terrified of the Skyliner. I don’t know if I could do more than once.
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I have one bookmarked too. Ill add this one, thank you.
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Definitely only doing rides and attractions that a toddler will be into. If we do the 4 RS rides it will be scheduled for nap time or when he’s doing other things with another adult. Lots of time allocated for The seas area, TSI, and DI animals. We love animals and zoos so this kid will just have to as well
So far Ive planned 3 hours morning, 3 hours evening. Meals and breaks around that. Does that sound reasonable? I’m ok missing most of the night time stuff. I don’t mind going back earlier with GS if the others want to stay, but doubtful they would mind having earlier evenings as well.
Yes. Just remember that the 3 hour evening block will likely also need to include dinner! (Morning block will need snacks but those are easy!)
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It would have to be a 2 BR. But now that I’m chunking AKL (sigh next trip AKL, next trip), I could probably swing it with out DH fussing about $ too too much. (He’s got me on one of those things called a budget, well, unless and Im now just thinking of this, I put up more 
, I like it!)
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I haven’t read all the responses. But I’ve done Disney with toddlers many times. I’ve never worried about making naps happen. My kids always just slept in the stroller. It’s vacation. As long as the adults get the kid might be off and can deal with it, it should be fine. Sometimes I might have to miss a ride to snuggle or walk a kid, or DH would push a stroller and skip sitting to eat. It’s fun if you can do “flexible.”
I haven’t ever stayed on property, preferring sprawling offsite houses. But I don’t think moving twice sounds pleasant. I’m sure there are hacks to make it either that people can help with.
We’ve also always preferred one park per day bc so much time is lost in the hop. And moving with strollers is awful. But the good part of strollers is you can bring lots of stuff to make the day easier and snacks and drinks and OOOOHH. I miss strollers so much. Our upcoming USO trip will be my first vacation without one ever. 
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This always makes me so sad to see. No, I wouldn’t. This trip is about GS and if he’s not happy, no one’s happy! We’ve been so many times so no need to do everything. We’ve also never been the type to forgo happiness and comfort just to do it all. That’s what the next trip is for (and the next one, and the next one)
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I’ve seen this before and had assumed this for our trip but they made us fold up our stroller on the Skyliner. Is it because it was a double? Or have they changed the rules?
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I bet it was because it was a double. We have two strollers for our trips and have never had to collapse one for the Skyliner.
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By the time we made our way to WDW, only my youngest was that young. I think I toured differently with her then (4th born 2 y/o) than I would have with my first (only kid 2 y/o)!
With my little then, she was used to napping on the go at home out of necessity shuttling her siblings around everywhere. With her, we did early morning RD, late night DPs and even DAH!
I think any plans you go in with, just hold loosely. As has already been said, Disney is incredibly overstimulating and he may throw you for a loop and acting off character!!
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This will be out of my comfort zone but we have at least 3 adults to care for the little one. That’s the priority. He’s the first grandbaby and already has Grampsie wrapped around his little chubby fingers. Well maybe Granny too 
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