There are frequent posts here from people who are overwhelmed with the amount of planning required for their WDW vacation. This is understandable - for many people it is the first time they are doing what I call a “destination/activity” vacation as opposed to a “relax at the beach” vacation, and this sort of vacation requires a lot more research and planning. Add to this the high cost of a WDW vacation, and there is a lot of pressure to “get it right”.
The first thing to acknowledge is that a WDW vacation in and of itself can be a stressful thing. Take for example the experience of a typical non-Liner family at WDW:
- They get up when they feel like it (“I’m on vacation, dammit!”), and stand around the resort lobby trying to figure out what park to go to and how to get there
- They arrive at a park well after rope drop, and immediately start their day standing in lines for bag check and park entry
- Once entering a park they get a map and try to figure out where to go – however, at this point it doesn’t matter because there are lines everywhere
- They try to get FPPs at a kiosk, and discover there isn’t much available except for it’s a small world
- They go to a TS restaurant for lunch, only to discover that they are not going to be able to get in because they did not make a reservation six months ago
- They stand in long lines, march all over the parks in the hot sun, and inevitably have a meltdown (“I paid a lot of money for this, so we are going to have fun, dammit!”)
- After a week of this they go home, and complain to everyone about how bad a time they had
The main objective of planning is to take that stress away from vacation time and spread it out over the months before your vacation. The fact that there are all these different “days” to keep track of (ADR day, FPP day, online check-in day, etc.) seems to cause additional anxiety, but I think that they actually help things, as they provide a framework that tells you what you should be focusing on at any particular time in the process.
More than a year out:
(What? You don’t plan vacations more than a year in advance? DW and I have been discussing our plans for a Fall 2018 vacation for months now…)
During this time period you should be working out when you want to go to WDW and how long you want to go for. There are several reasons you may want to be thinking about this so far out:
- If you are planning on using/renting DVC points, the first (and sometimes only) reservation window starts 11 months out
- If you are going to use frequent flyer miles, for many airlines the reservation window opens 330 days out and the available seats can go quickly. Ditto for hotel points, although they vary wildly between the major programs (for example Starwood starts at 18 months out).
- The base prices for WDW tickets only go up, so if you see a good deal for tickets that will be valid for when you want to go, jump on them
- If you have a particular WDW resort in mind, you might as well book it as soon as you know when you will be going. If a discount is offered after that, you can always call WDW Reservations and have it applied to your reservation.
One year to 180 days:
During this time period you should be working out what park(s) you want to go to on each day – your go-to source for information to help out here is the touringplans.com Disney World Crowd Calendar, which gives you predicted hours, crowds, and special events. As you get closer to 180 days, the calendar will be updated with actual park hours posted by WDW and revised crowd predictions. Once you have determined your park plans you can then figure out what ADRs you want to get (or vice-versa, if certain dining experiences are a priority).
Many people (myself included) also like to start making Personalized Touring Plans to get a better idea of what each day may look like. The thing to bear in mind here is that the predicted Crowd Levels are going to change, so these plans are definitely going to require some further work. However, it is useful as it gets you comfortable with the software and it helps you determine if you have a reasonable number of activities planned for each day.
Note that the main WDW calendar only has park hours posted up to 180 days out. See this post for ways to get accurate park hours beyond this limitation.
180 days – ADR Day!
My main tip here is to open up separate browser windows and set them up for each ADR you want to make, and then once the reservation window opens launch them all at once. Then keep cycling through each window as you progress step-by-step through the reservation process. If you can’t get all the reservations you want, don’t despair – try the touringplans.com Disney World Dining Reservation Finder. Many Liners have been able to get hard-to-find reservations using it.
Another tip is to avoid the traditional meal times when planning your meal breaks – most people are creatures of habit and want to have lunch at 12:00 and dinner at 6:00. If you schedule your meal breaks before these times you will avoid the crowds at the restaurants and then you will be back out touring when many people are trying to eat. Zig when they zag!
Bonus tip: Before you reach day 180, log into your Disney account and make a few practice reservations. This way you are familiar with the process and how the website operates, and you can make sure that your credit card info is correct. Just remember to cancel the practice reservations. 
180 days to 60 days:
Now is the time to start to get serious with the park planning! Use this time to start making and/or revising Personalized Touring Plans for each park day. The goal here is to make plans based on what you want to see and do and then use them to determine what the best FPP options are for you – I have another forum post that sets out a methodology for doing this.
60 days – FPP Day!
Try to get the FPP reservations that will work best with the Touring Plans you have made. However, don’t worry too much if you can’t get the absolute best FPPs – remember that having a good plan in the first place is the real time saver here, and FPPs are just icing on the cake.
60 days to Day 0:
Adjust your Touring Plans based on the FPPs you were able to get, and re-optimize when the predicted Crowd Levels are updated (tip: use the touringplans.com Disney World Crowd Tracker to get e-mail notifications when predictions are updated). However, don’t stress too much about this or start to re-arrange everything – you have a good plan in place, and it will make a big difference no matter what the Crowd Levels actually turn out to be.
Another thing to do is to get your room request submitted to WDW if you are staying on site. Touringplans.com makes this very easy with their Automatic Room Request feature. Just follow the instructions in the link, and touringplans.com will automatically send a room request fax to your resort 5 days before your stay starts. (Thanks to @PrincipalTinker for suggesting to add this!)
Day 1 and Beyond:
Use the touringplans.com Lines App to track your progress in the parks. Avoid the temptation to re-optimize throughout the day – my recommendation is to only re-optimize if you start to go significantly off plan. If you do re-optimize, make sure that all the things you have completed thus far are marked as “done”, with the most recent thing you completed marked last so that the app knows where you are.
Final thing to remember:
“In preparing for battle I have always found that plans are useless, but planning is indispensable.” - Dwight D. Eisenhower
In other words, don’t despair if on the day your plans don’t work out exactly as you would like them to. There are so many variables here that are not within your control, and something unexpected like a headliner attraction going off-line can cause major crowd movements and throw everything off. The upside here is that with all the planning and research you have done, you will be in a better position to react to what is going on and deal with it in an efficient manner.
