Choosing WDW travel dates (Part 1)

McSweaty Family - Animal Kingdom Park. When should we go to WDW?
McSweaty Family – Animal Kingdom Park

As we previously discussed, our trip window opens this fall. Now we look at when we should go to WDW. If we want to go before the end the year we’ve got a few options. I mentioned my wife, Ashley, is a teacher. Because teachers get a pretty decent number of days off in general (summer anyone?), she doesn’t get a ton of personal days. For the year, she gets five personal days total. She actually has to pay for her fill-on on the fifth day.

As such, we usually try to vacation when school is closed. Unfortunately, those dates typically coincide with some of the busier or more undesirable (summer anyone?) times to be at WDW. You might say, “But Aaron, doesn’t scheduling your Disney trip around school closing also benefit Lorelai, your first grader?” and I would say “oh yeah…I suppose so, probably.”

When should go to WDW? – some options

Back to options. If we’re going to try and go when school is closed (or partially closed), we’ve got Labor Day weekend, fall break, Veterans Day weekend, Thanksgiving, Loi Krathong, and Christmas. How about a pro / con list to organize our thoughts?

For our pro / con list, we’re using MouseSavers’ WDW 2019 resort rack rates to look up rate “season” classifications. Crowd classifications are based on inside information from Kenny the Pirate. There’s also a very real chance they are based on Dave Shute’s site and his best weeks ranked.

We haven’t nailed it down yet, but we’re going to assume a 5 night stay on this trip for the time being. We’ll use a Pop Century standard room as our sample resort to show you the pricing differences per night.

Labor Day Weekend


  • Earliest date in the fall trip window – it’s been a while and we’re itching to go as soon as possible.
  • Have had some of our best WDW trips on Labor Day weekend. Granted, most were during “Great Recession” of 08-10 where you could stay concierge at the Polynesian Village for less than a cup of coffee a day, but still…
  • In “Value 2” season pricing ($144/night), seeing lower ticket costs ($114ish), and better package discounts (e.g. “free” dining promo) for these dates.
  • Week after Labor Day weekend historically sees some of the lightest crowds of the year…even with the recent trend of crowds shifting from summer to fall.


  • Still hot, still humid, still hurricane season.
  • Limited time due to only one day of school close (Labor Day) – will have to miss an additional 3 school days to squeeze in a 5 night trip.
  • College football season kick-off weekend – we’re playing Duke so I don’t expect a nail-biter. Course, said same about Clemson in January…and it wasn’t a nail-biter. Still biter bitter.
  • We’re still waiting on firm opening dates for Mickey’s Runaway Railway at the Studios and the IllumiNations replacement Epcot Forever over at (you guessed it) Epcot. However, with Disney’s construction track record, I’d say there’s a better than 50% chance that we’re too early for both with a September trip.


  • Not-so-scary Halloween party dates give us opportunity to take Lorelai and Ben to their first party (cheaper ticket in September) but also closes Magic Kingdom early for the nights we don’t attend.
  • Food and Wine Festival – gives us more food options at Epcot than normal (though you have to work hard to find Epcot in a non-festival state these days) but makes World Showcase more crowded and unpleasant overall – especially on the weekends. The “Eat to the Beat” schedule release may help us better classify depending on the band.

Fall break (early October)


  • Weather a touch better than early September.
  • Into “Fall” resort pricing now ($159/night), but still reasonable.
  • Tickets prices essentially same as September.
  • More time as school closed for 2 days – only need to miss an additional 2 school days to squeeze in a 5 night trip
  • Probably up to a 75% chance that both Runaway Railway and Epcot Forever are open – might even put Epcot Forever up around 90%.


  • From wait times and trip reports over the last few years, October is one of the more crowded months of the year – we’ll miss the typically busy Columbus Day Weekend so that’s something.
  • “Free” dining promo option goes away as we get into October.


  • Not-so-scary Halloween party dates – see previous – party tickets more expensive in October
  • Food and Wine Festival – see previous. Again, “Eat to the Beat” schedule release may help better classify depending on band -example, “Baha Men” drop Food and Wine Festival into “con” classification.

Let’s pause here and pick up with the rest of our 2019 date options in the next post. We’ll also see if we can make a decision on when we should go to WDW before moving on to picking a trip length.

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