How far out do you start planning?

After our 2014 trip when DD8 was 4, I decided I wanted to come back when she was 8 during her Spring Break so I had April 2018 on the radar since then. I started to really start to think about where we wanted to stay about a year out, then rented DVC points at 7 months which gave me a month to figure out ADR's. We live on the West Coast so it's a big deal to come out compared to DL - I am hoping we can go again to WDW in 2022 when DD is 12. I figure at each 4 year interval, she's a totally different kid with different interests so it will be a new experience each time for us all and in 2022 we'll be able to see Toy Story Land and Star Wars land too.
 
I like to start planning as soon as I know for sure I will be going. I already reserved my room for my March 2019 trip, figured out what ADRs I want at what times, and which FPs I want at what times. I can’t figure out HS FPs yet, but the rest I already know. Now I just need to wait until October to start booking ADRs!
 

I guess it depends on what "planning" means to you. We've been enough times and I stay updated on what's going on at WDW enough that I can put together a good trip as long as I'm within the 180 day booking window for dining. We know what we like, we know how things work, so I don't need a ton of time to make it happen. I come up with a rough "we'd like to go in 20xx" and then fill in the details when needed.
 
Currently planning our 3rd trip in 17 months. Booked at 205 days out and I look up information every few days. I love planning trips, not just to WDW, so having one booked even if it’s months out is necessary for me!
 
I'm in a constant state of planning for Disney. Right now I have the trip coming up in June of this year. All that's left for that is FastPasses and I'm set. But the deposit is already paid for DVC rental for June 2019, and I've knocked together a rough plan for that one too. And my hope is that I'll basically be returning every June (or maybe December some years) for the foreseeable future. 2020 is already in the back of my head because I don't know if Star Wars land will be open yet in June 2019, so I'll have to return in 2020 if it's not! I figure after a few more visits, I'll have my WDW routine down. It's weird that I've actually only been three times in the past 20 years (one of those times was almost 20 years ago, once in 2016, once in 2017). I feel like I know the place like the back of my hand, but I have the DISboards to thank for that! That and my relentless Clark Griswold-esque devotion to vacation planning. LOL!
 
I’m currently pregnant with baby number 2, and I’m already dying to start planning his first trip! DH and I are talking about going during either February or April school vacation weeks in 2020, so about 2 years from now. I’ve already started to try to get rough estimates on cost for a family of 4, list things we haven’t done yet, look at crowd calendars for those times of the year, etc. I’m not crazy for thinking about this stuff already right?! (If I asked my husband it would be yes, he loves Disney almost as much as I do but he’s super laid back about planning and such haha)
For our past two trips I booked everything around 6 months prior and spent that entire time until we left on here/mde/etc. working on the details. So I feel a little silly thinking so much about a trip I can’t even book for quite a while, I just miss WDW so much!

So, what do you typically do?
Planning is half the fun of the trip! There is so much information to process between here and Pinterest! I love it! I bookmark tons of websites. It's gratifying gathering the information to put it all together. It makes me feel so prepared for my trip. I love reading all the updates about the park, rides, foods. I have packing lists ready to go, including Fastpass options, & Disney dining options in each park and other options. My husband thought I was obsessed doing all the research, but he realized it causes a great relaxed trip. Enjoy it!
 
I have planned WDW trips anywhere from 17 days (current trip) to 10 months out. That said, the majority of my trips are planned 5-7 months out.
 
Christmas Day of 2017, we booked our first Disney World trip together for December 4-11, 2018!!!! Sooooooooo excited!!!!
We both have been to Disney World many times before, but this is a special first trip together!! :)
 
Planning a one day trip in April (will be in Orlando for work), family short time in September 2018 and also starting to plan November/early December 2020.
 
So thinking about? We are going again in 2020 and I'm thinking about it now! :rotfl:

Usually we book a year out, but this next trip will be different. We are planning to stay at Yacht Club in May of 2020. By then Star Wars Land will be open and I'm expecting an uptick in reservations/booked hotels in that area. So we are actually going to book a room only at 499 days, which will be sometime this December, just to make sure we've got a room locked down. First time doing that!
 
We go the same time every year, and I always start thinking of our next trip on the way home from our Disney trip. Drives DH nuts, the whole car ride home I’m talking about where we should stay, what we should do, lol. I love planning and it helps with the Disney depression.
 
Here is a follow up question-
We just booked about 11 months out. I LOVE countdown chains- those with kids, do you countdown the days (361) or the weeks (45)
till Disney?
Our last trip we booked and counted down from 27 weeks and then did a 30 day downtdown.
This time I am thinking of days, but breaking up days till our Sept Beach trip and then from beach to disney so it would be about 153 days on each.
 
...Start??

I guess I started planning six months before our first trip (several years ago) and have never actually stopped planning since!
 
We watch a Disney movie every weekend in the months leading up to the trip to get everyone psyched for the trip, and more frequently in the weeks before we leave (and in the van on the drive down). They enjoy the parks more when they can recognize the connections to the movies they’ve watched. I go to the library and find old Disney movies I don’t see elsewhere and kids haven’t seen before, like Swiss Family Robinson and Country Bears. Also starting 6 months before, half the kids monthly allowance is given on a Disney GC. They also get a Disney themed item weekly (things they need for the trip-new Disney clothes, new autograph book or whatever) before the trip. So we don’t do a countdown per se, but we do things to get them excited and ready.
 
We haven't even gone on this years trip yet and I'm already planning next years! :rotfl2:
 


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