Just gotta say, the new multi-quote is hard to get used to...that's what happens when you take a year break from the DIS (It is pretty cool that I exited last night and it saved my response though)
We leave in the 9th so I'm planning on telling him on that Friday before we leave. That gives him a few days but most of them are weekend/holidays.
Kids don't need a lot of time just a few days to adjust. So I don't think he needs weeks like older kids or teens.
I Would get at least one FP for one or two rides that are "thrill" rides if you think he might be interested. That way if he says ok you dont have to wait in a long line only to have him decided to not ride after watching/hearing the ride. Sometimes that changed kids minds. Lol
He might surprise you as to what he will do. My favorite old trick is.... He looks younger then you and see he loved it! ( watching people coming off the ride. Lol)
Regardless there are enough rides that he will enjoy to fill your time. I can't stand parents that drag a crying screaming child one a ride even if they end up loving it ( which I don't think you will do )
Right now, I'm trying to decided between Splash Mountain and Thunder Mountain. More from a "where would FP be most valuable standpoint." If he gets up to the front of the line and doesn't want to ride, it's not the end of the world. I'm not a lover of Splash, but I certainly don't want to wait in line for it forever either, and think it would be good to have a FP for it right before we leave for our break that day. I think we could do Thunder Mountain fairly early in the morning after the Mine Train without too much trouble. Soarin' is definitely on the itinerary, but I think we'll skip Dinosaur.
When my kids were 4 and 6 we surprised them.
It was great. We all have a great memory of them seeing the Disney sign and figuring it out. It was wonderful and magical and we ALMOST did exactly the same thing for this trip.
But there were some planning things that I wanted their input on, so we told them a month before the trip. It has been GREAT talking about it, getting excited, watching Disney movies, watching the Disney video (over and over.)
Good things about either approach!!
The planning is difficult, even beyond the FPs. Choosing between Value resorts has been hard, because honestly the only one that appeals to me is AoA, and of course it's completely booked for our dates. So I narrowed it down to Movies and Pop, then chose Pop, because I've always told myself that if I had to stay at a Value resort that would be the one (pre AoA). It would have been nice to have DS's input, but he'll love either. There's a slight possibility that our original quote for CSR was wrong (my TA caught it, but she's super busy this weekend, so she hasn't been able to double check yet, and I just wanted an on property res to lock in FP before it opens to the general public next week) and if that's true, and the new quote is low enough. then we'll be staying there instead. DH loves his creature comforts. So, it may be better that I didn't give DS the super fun kid friendly options, then switch to somewhere else for his Daddy's sake.
DH is basically useless when it comes to planning. He loves Disney, but doesn't love to talk about it. He told me last night that he trusts my planning, which is all well and good, but it's not an easy job, even when it is super fun. Now I'm thinking that if we do switch, I'm going to surprise DH. So he can think we'll be staying in the tiny room with a rubix cube staring us in the face right outside our door. The potential issue with that is if he starts talking up the hotel we're staying at for DS's benefit after we tell him.
I hate surprises, but I know other people, who aren't as much of control freaks as I am, love them.
I am planning to surprise my 5 and 3 year olds a day before our trip with a call from Mickey Mouse himself ! Followed by a surprise goody bag filled with autograph books and such "tinker bell" gifts. This is the first time we are doing the Mickey Mouse call but we do a tinker bell gifts each morning of our trip themed according to the day's activities, just some economical items as flip flops or such for a water park day or glow sticks for a fireworks night etc also for character dinners I make out a cute invitation card that I give out as tinker gift the morning off for surprise!
It's just so magical to see the expressions on there face ! Priceless !
Right now, I'm thinking the best time to tell him would be Friday after he gets home from school. The flight I'm considering leaves at 6:45am on Sunday morning (and we still don't get to Disney until 6pm!) so we'll be driving in on Saturday to stay with one of my parents before we leave.
I do need to start getting all our Disney stuff together. Definitely need to make sure our fans are in working order, and possibly buy a few more. Then figure out water delivery, if we won't have a rental car to go get it ourselves.
We are surprising our two children, age 7 and nearly 3 at time of travel. At the moment we plan to tell them either a week or a few days before. I know they will love it

. When we tell them, we are going to leave out a slight detail, staying at the GF! When we pull up our DD age 7 will not believe her eyes.
One reason we aren't telling them is that we have over a year before we travel and they would not stop asking 'how long until we go'. It doesn't stop me talking about it and looking at rides on YouTube with them though! I just say 'whenever we next go to Disney' and they are non the wiser.
I don't know how I'm going to keep this secret for so long
Haha...yeah...a year would kill me. If we weren't going in 6 weeks, I probably wouldn't even consider attempting a surprise. I did the "next time we go to Disney" thing with DS before our potential trip last year. Maybe that's why he's still obsessed with it? I didn't tell him about that one, because I knew there was a high chance it would get cancelled, and then it did.
My mom said to us when We are young We go to Montreal! When! Now! Go up, pack your things, We take the bus for 6am. I hated that! I loved to go at Montreal (We lived at 800km of there) but i forgot lot of think like my underware! My grand-father was the type We going before you go out of Bed and my mom learn this of him.
I hate surprises! Hate hate Hate!
I am a planner, i plan also the unplanning lol! I like anticipation. I love to Check where i go and all fun i can have.
For the height thig - just because your doctor measured him at 40" doesn't mean the Disney sticks will measure him at 40" but you should make his FastPasses for those attractions you think he will be interested in.
As for surprising at that age, my son and daughter-in-law (well, she became my daughter-in-law on that trip

) decided to not surprise my granddaughter on her first trip. She didn't know she was there until we pulled up to the first purple sign. While the trip was great, what my daughter-in-law said later was that if would have been nice for my granddaughter to have had some input and insight into what she was getting into since the only thing she'd ever been to was Cedar Point and Disney World was much more than that. That's not the case in your situation but the input would have been nice. On their second trip, now with my grandson in tow (five at that time as well), the kids got the news a week in advance so they could help with planning.
He actually measured at 40.5 inches without shoes, and he wasn't standing up very tall. That's something I probably should work with him on too (not being afraid of the stick). With shoes he'll probably be over 41, even if he slumps a little.
The issue with getting his input a week out is that FP availability will be less than what it is now. Restaurants the same deal. So other than, what do you want to do first "Peter Pan or Winnie-the-Pooh" there won't be much planning he can help me with.
I am considering adding Water Parks once we get there, but I think it will be too much, and I'm not sure the budget can support it.
I would definitely surprise him, BUT show him videos of all the fun things you will want to share with him. I would say things like ...the last time we went to Disney, you weren't allowed to ride this, now that you are taller and older, you could. Or this is my favorite ride, maybe some day when we go back, you will want to ride with me.
Stuff like that to get him in the mind set that you want to do all these great rides with him, but that it is in the future.
Anxiety can be very difficult when you have to consider the family dynamic when planning.
For example, we have had annual passes for many years and once surprised the kids with a day off of school to go to Disney (they were still in public school at the time)
My son was in 4th grade and my daughter (she hates surprises by the way) was in 5th.
DS was thrilled to even have a day off and when we drove under the MK signs was fist pumping my DD and all excited.
My DD, however, was upset because she would miss chorus and was afraid her teacher would take her out of the school play because she missed practice.

I am happy to say that the minute we drove into the parking lot she was not at all concerned with missing chorus and had a great time.

Sorry for the digression...I just had to share that with you from another parent who has a child who is anxious sometimes.
That's a good idea. Luckily, he's our eldest, so there won't be much difficultly catering to him. DD won't be able to ride any of this stuff, so if he decides he doesn't want to, we can just move on. I actually enjoyed being able to plan without most of it, during our last trip. We did single rider for some of our favorites. It's easier to fit things in when you don't have to choose between a FP at TSMM and RnRC.
Yeah...most of my siblings would be the kid who would freak out about missing school. I don't think DS will, but it does make me nervous that he hasn't even started the year yet, so I have no idea what he'll be missing. I doubt they'll plan anything super cool that week but...
Since we'll be leaving on the weekend, and he has zero grasp of how long it takes for time to pass, I don't think he'll actually make the connection that he's missing school. But if he misses a jar party, or something like that, he might be upset. I think it's early enough in the year that we'll avoid most of that though.
Was a nervous kid, now a high strung adult...no surprises.
I would suggest if you are set with a surprise idea, tell him you are going to some surprise place and give him really random clues and tell him you will let him know where you are going on a certain day. If he guesses before do not tell him...make the rule that he has to guess everything exactly right for you to reveal the location. Maybe he will guess early, which will hopefully make nervous energy excited energy.
Tell him ahead of time when you are going to be giving him clues, like every Tuesday or after he brushes his teeth or come home from the dentist or some task your child does not like. This will help encourage him to do the task or look forward to it, feeding him positive reinforcement the whole time!
Make up all the clues before you reveal the first one.
When the time comes, do the reveal, and watch videos about the trip! A few years ago, my hubby did this set up as a birthday trip. It was for a weekend away at a beach town b&b and whale watching. His clues where blue, brown, 83, wood, metal, an animal that begins with D, the letter B, sand and a wave symbol. Lol.
Instead of being upset about being surprised, I was excited and engaged in the whole game. All of my coworkers were trying to guess my surprise too. I actually guessed about 90% of it but got the wrong beach city! Lol!
Interesting perspective. He would probably guess Disney World on his first guess though, because for some reason he thinks that's the only place airplanes and trains go....