Tales From The Walt Disney World Planning Trenches


We’re finally doing it – we’re going to Walt Disney World. In a couple of months, we will fly down to interior Florida and spend six days within the 40 square miles hailed as the Most Magical Place on Earth. Earlier this year, I wrote about all the reasons why we’ve chosen other destinations over Walt Disney World for vacations so I do have to chuckle that we’ll end up visiting Mickey less than a year after I published that post. Why the change of heart? Well – there are a handful of reasons why we decided to bite the bullet sooner rather than later…

  • Our kids really want to go. People certainly don’t accuse us of taking kid-centric vacations (pictures from our visit to Stonehenge exemplify this fact). When we visited Disneyland almost three years ago, Clay and I planned the trip with the idea of “We’re doing this for the kids…“. Well wouldn’t you know – I think Clay and I ended up enjoying our three days at Disneyland more than the kids. While our kids really do love our families adventures, they’ve mentioned a few times how they’d like to visit WDW. And truth be told, Clay and I do too.
  • Armed Forces Salute tickets aren’t getting any cheaper. Look – Disney World is not an inexpensive vacation. Disney has offered the Armed Forces Salute off-and-on since 2002 at varying discount levels. Since 2009, the Armed Forces Salute ticket prices have increased each year. We’ve always known we’d visit WDW eventually so early 2020 seems as good of a time as any to finally take the plunge. According to the WDW website, a 4-day non-park hopper ticket that allows guests to visit one park per day is $335/ticket. For comparison, we purchased 6-day Park Hopper ticket vouchers at Fort Belvoir for $301/each.
  • We want a winter escape. Washington DC is the winter is beautiful. There is nothing quite like seeing all of the monuments covered in snow. But by the end of the January/beginning of February timeframe, we’re always itching to escape somewhere warm for a little while. Only caveat? It is not cheap. When pricing tropical destinations to visit this winter, we mentioned, “Geez, visiting these places will cost more than Disney World!” We originally started to plan to visit over Spring Break (apparently we felt like being gluttons for punishment) but last week, we decided that we wanted to go as a mid-winter break from the gloomy DC weather instead.
  • We don’t know where we’re going next. We’re anxiously waiting to find out where the Army will send us this upcoming summer. We’re hopeful that we will be able to go on another big adventure this summer (Italy? Road trip up into the Canadian Rockies? Alaska? Ireland?) but with so much uncertainty tied to report dates and unknown locations, we’re bracing ourselves for the possibility of needing to scale back our big summer trip this year. We’re going to try our hardest to squeeze something in though!

The Not So Overwhelming But Still Intimidating Planning Process. This picture of Violet at Disneyland is exactly how I felt going into the Disney World planning process. Before kids, Clay and I would fly across the country without hotel reservations – instead choosing to Priceline a hotel upon landing. We loved the adventure of the unknown. And we love a good last minute trip. For example, a couple of years ago, we received our household goods and booked a vacation package to Deerfield Beach, Florida that had the four of us flying the next day. That’s how we like to roll, which is pretty much the opposite when it comes to a WDW vacation. It didn’t help that people would say things like, “Wow – you really are booking your trip last minute!” Since when is booking a trip 70-days out considered last minute?!?

So last weekend, I put out an SOS message on Facebook and within minutes, I had a bunch of people holding my hand telling me that it would be okay. By Sunday night, we had reservations to stay on-property and reservations for one sit-down meal each day. By Tuesday night, we had ticket vouchers in hand and plane tickets reserved. And now here we are – just waiting for the 60-day FastPast window to open up. We chose not to use a Disney Planner because we actually found ourselves enjoying the planning process and sitting side-by-side on our laptops researching various aspects of the trip. If that isn’t romance, I don’t know what is. In the past five days, we’ve completely planned a WDW trip, we’ve watched the first two episodes of The Imagineering Story on Disney+, and we’ve binged on related YouTube videos so we’ve pretty much jumped into the WDW pool cannonball style.

The excitement is building and we’re fully embracing the dorky Disney family vibe. Will mouse ears be involved? Yes. Will we wear coordinating Mickey shirts? You bet. Will this trip launch a yearly pilgrimage to WDW for our family? Nope. But I have no doubt that our visit to the most Magical Place on Earth will be a fantastic week for our family.

What are you MUST-DO’s at Walt Disney World? Those of you who are well-versed in Disney culture or have visiting WDW before, I’d love to hear your favorite things to do while in the parks. Is there a certain restaurant that you love? A ride that’s worth waiting in line for if a FastPast+ doesn’t work out? A certain snack that no trip to WDW would be complete without having? What is your favorite life-hack related to WDW? I’d love to hear it!

5 comments on “Tales From The Walt Disney World Planning Trenches”

  1. My FIL and SIL both work at Disney World, so we’ve spent way more time there than I ever would’ve planned 15 years ago! My must do Disney advice isn’t a location- it’s a rule we now live and die by. We call it the “one thing rule” everyone chooses the one thing that is most important to them, it can be a ride, experience, restaurant, photo op (that’s usually me) etc. I’ve found it’s really helped manage expectations especially if you’ve got a grandparent involved who expects your three year old to be filled with awe and wonder every single moment- but that’s a story for another time! Our rule is we will do everyone’s one thing unless extenuating circumstances occur, the second part of the rule is when we’re doing someone’s one thing, there is no whining, fussing, complaining or otherwise ruining it for that person. I’ve found as my oldest has gotten bigger, it helps to watch Disney Food Blog on YouTube and ride reviews to help him choose. Sometimes our one thing is per day/park sometimes it’s for the trip. It depends on the group etc. I also have everyone list their top five choices to help me plan! Good luck- you’ll have a great time!


  2. Oh, I so needed to read this today. We’re a military reserve family–are you still staying on Disney property with the Armed Forces tickets? I am panicking because I have not done much of anything and we are hoping to visit WDW in April/May. We have historically vacationed the same way as you–we love to just wander and explore (cities, mostly) but that is NOT (apparently) something you can do with Disney. Any essential military planning tips? Our kids are 8 and 5 for what it’s worth.


  3. We are staying on a Disney Property with the Armed Forces Salute tickets. They’re actually vouchers, but they have the ticket number on them so we were able to link them to My Disney Experience. When we arrive at WDW, we will just have to exchange the vouchers for actual tickets at any ticket window location (including the one in Disney Springs!). We were able to order our Magic Bands have them linked with the vouchers. Our kids are 10 and 6 so like yours, they’re the perfect age because they’re able to go on almost every ride. 🙂 Have fun planning your trip! We’ve enjoyed the planning process more than we thought we would!


  4. How cool is it that you have family that works at WDW? You have some great advice and I LOVE the ‘one thing rule’. We’re currently applying that as we prepare for our FastPass day.


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