Planning a Disney World Vacation: Part 3

(You can find the previous posts here and here!)

OK.  Now we’re getting into the actual planning process.  This goes beyond dreaming and into the “Hey, I’m thinking of going for it” phase!  So, where to begin??


There are several things to think about when planning for a trip to Disney World.  

  • When do I have vacation?
  • When are the kids out of school? OR do I take them out of school for Disney?
  • When is it busy, less crowded, or outright insane at Disney?
  • When are special deals offered? Are certain times more expensive than others?

For us, the when was easy for two reasons.  I already knew that Disney has lower crowds at the end of the summer when lots of kids are already back in school, but mine aren’t. (Lucky!)  And, since our nanny goes back to college before my kids go back to school, we had a week with no childcare anyway!  My Mom is retired, so she’s good to go as long as she doesn’t have another trip planned (She’s the queen of chartered bus trips.  Seriously, she goes on about 1-2 per month!) My sister works for a school district in Kansas and they will be back in school, but she is able to get off with enough notice.  

Also, last time we went we got in on the “Free Dining” deal that comes out almost every fall.  We also got that deal again this time.  Included in our package is one “table service” (sit down and get waited on meal), one “quick service” meal and one snack per day plus a refillable mug for drinks at the resorts.  (More info on the dining plan later!)

Here’s where the 3 levels of planning come in.

As a reminder, I’ll be breaking everything down into 3 levels.  MUST-DO (The minimum amount to get by and have a great trip!); EXTRA-MAGIC (Knowing those special details that will make your trip even better); and MUST KNOW EVERYTHING (For those who want to fall down the rabbit hole with me and become a Disney World know-it-all!)

MUST-DO: The best way to plan when to take a trip to Disney, is to look at reputable crowd calendars.  The best look at the year overall (from my very favorite Disney planning site– more on this later!) is THIS ONE at  It shows the easiest way to see the most important thing to think about: CROWDS! It’s awesomely color-coded so you can see the most and least busy times during the year.  If you have all the flexibility in the world, look for those bright green dots and go for it!  If you have some flexibility, use the chart to find the best dates for the times you have available.  AND, if you only have one week of the year to go, and it happens to be Christmas week (the busiest time of year at the happiest place on Earth…), well, a good touring plan and great running shoes will be your best friend!  (Touring plans to come in the details section!)  The week we are going is listed as “Light Crowds”.  We found this to be true on our last visit with little waits at most major attractions at certain times, but longer waits during peak afternoon hours no matter what.   

EXTRA MAGIC: If you want to think about more than crowds, digging a little deeper will help you figure out more info that may help you decide when to go.  You may want to know if there are any deals being offered during certain times of the year, any special events held at Disney World that you’d be interested in, crowd breakdowns by day and by parks, weather during certain times of the year, etc.  Josh at has some great “extra magic” details.  You can go through his month-by-month breakdown HERE where he talks about costs, weather, crowds, park hours, entertainment options, refurbishment schedules (when your favorite rides may be closed!!) and special events.


  • There are tons of crowd calendars out there.  I linked to two above, but google for more and see when they all agree on the less crowded times! (Try this one or this one to get started!)  
  • Go to and search packages for several dates/times to see when the best deals are offered.  Click through several package options to see which is the best for you.  Is Free Dining a better deal? Or would you rather just get a 30% room discount?  (I may or may not have several spreadsheets with various dates, prices and package configurations listed so I can compare!!) 
  • Sign-up for the mousesavers and earsthedeal newsletters to get notified of upcoming discounts on and off property.  
  • Thinking of going often?  Maybe look into the Disney Vacation Club option! You can even rent points to use at DVC resorts if you don’t want to buy in right away!

Ok, I was totally planning on talking about how long to go and when to book, but this is long enough!!  I promise I’ll get to that next time!  Stay tuned…


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