First-Timers: Don’t Make These Totally Embarrassing Disney World Planning Mistakes

by | Apr 8, 2025 | Walt Disney World

Heading to Disney World for the first time? They are the Disney World planning mistakes to avoid, according to an expert.

I always say the ultimate Disney Dad is our old pal Goofy. His heart is always in the right place, even when his head isn’t. That’s how I was many years ago when we were planning our very first Disney World adventure, and I made some of the all-time classic newbie Disney Dad mistakes. But you don’t need to make your own version of these Goofy mistakes because I already went and made them for you. You. Are. Welcome.

Disney World Planning Mistakes to Avoid

Wear the Right Shoes

As a first-timer, you don’t entirely realize exactly how much walking you’re signing up for, and that’s why you “saved all that space in the suitcase” by planning to do the entire holiday in last summer’s largely defeated walking sandals. Not a change of footwear in sight.

You probably thought you were being really clever, because I sure did when I made the same mistake. Fortunately, I married someone a lot smarter than myself who wasn’t above re-packing my suitcase when I wasn’t looking. (Gawrsh, thanks, Mama Bear.).

Strollers May Be a Must

Back home, my daughter had graduated from the stroller set long before we made our first trip, and it never occurred to me that she would be taking a trillion steps a day on her tiny little legs. Rent a stroller? “She probably wouldn’t even use it.” She was a trouper. Kept up with the group. Never complained.

stroller rental at disney world

Photo by Cliff Wang

And after a few days of nonstop strollerless fun she was so exhausted she passed out at the table in ‘Ohana, after eating exactly one peel-and-eat shrimp (easily the most expensive single crustation I have ever bought.). Needless to say, she rode the rest of the holiday in style.  

Forgetting to Make Dining Reservations

It’s an easy mistake to make… Advance Dining Reservations feels like a competition. Sixty days until “GO” time, and you haven’t had a chance to take much official action since you booked the holiday in the first place. It’s only natural for a well-meaning but extremely Goofy Disney Dad to book three sit-down meals per day – a.k.a. an entire holiday’s worth of breakfasts, lunches,s, and dinners. Isn’t it? Whoever has the most wins, right? At least, that was what I thought.

Fortunately, we had some more experienced Disney friends who were able to talk Mama Bear and me out of this particular banana tree by pointing out that if we stuck to this schedule, we would spend the entire holiday eating frantically, with both hands… if we could even get to restaurants that were often far afield and not necessarily anywhere close to our park plans for the day.  

Involve Your Family in the Planning

YouTube, social media…, and even Disney’s own advertising all teems with perfect videos of perfect parents surprising perfect children with news of a surprise Disney vacation. It’s only natural to want to try it yourself. Besides, how many times do you want to answer the question, “How many days until Disney, Daddy?” Keeping it a secret just made sense!

disney world for multi generational families, disney world tickets vs annual passes, cinderella castle

Photo by Marisa Alvarado

Like a lot of things that “just make sense,” it was a mistake. Luckily, my wife, and I are terrible at keeping a secret, and we told our mini-menagerie the news much earlier than we intended. As it turns out, with enough time to involve them in some of the planning and to discover that there were things they were dreaming of that we would never have guessed! And to top it all off, when we told them, the little stinkers didn’t even believe us! So much for our photo-op surprise, but ever since, our kids have trip-planned with us at every step.  

Get ready to make your own mistakes!

Because you will, and they’ll be spectacular! Years from now, you’ll laugh about them as you dish out tips and tricks like the expert Disney Dad you’re already turning into. But whatever they may be, as long as they come from the heart, you’ll never go far wrong!

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Authored by
Gregg Taylor

Gregg Taylor, Disney World Expert and Dad | Gregg has been with WDW Magazine since 2020, where he serves as Membership Coordinator. He has been planning and executing awesome Walt Disney World adventures for more than a decade. Gregg has written and produced nearly two hundred full-cast audio drama episodes for the Decoder Ring Theatre podcast, as well as a number of direct-market print and audiobook adventure and mystery novels in the continuity of DRT’s programs Black Jack Justice and The Red Panda Adventures. His comic-book adaptation Mask of the Red Panda, created with artist Dean Kotz, was published digitally by Monkeybrain comics and in a collected print edition by IDW Publishing. Gregg was nominated for a 2016 Canadian Screen Award for Best Original Interactive Production Produced for Digital Media.