Not My Vacation. Part One: Before My First Trip To Disney

Hi. My name is Lindsay, I am 33 years old, and I have never been to Disney World.

And here’s another confession- I have absolutely no desire to.

Yep, I said it. Because that’s apparently what happens to children who grow up never having experienced the magic that you can (supposedly) only get at a Disney theme park.

I just don’t get all the hype. Not even a little bit. I don’t know, there’s something about spending thousands of dollars to walk 27 miles a day and stand in super long lines in the hot Florida sun that just doesn’t Tinker my Belle, so to speak. A world of sunburn, blisters, and bankruptcy isn’t my idea of the happiest place on Earth.

But I’m a mom and you know how we try to do better for our kids than we had and all that blah blah blah. So now I’ve found myself facing a dilemma. Mirror, Mirror, on the wall, who’s the coolest Mom of all. Apparently it’s me because WE ARE GOING TO DISNEY!

I seriously considered taking my 5 year old son to Six Flags and telling him it’s Disney. Is that bad? I can just imagine it now- him announcing to his class that he goes to Disney three times every Summer. The one in Eureka, Missouri.

Now come on, it’s no worse than telling him some strange woman flies into his bedroom at night to buy his teeth while he sleeps, right!?

But I’m just gonna be honest. That is why we are doing this after all. For the street cred. That, and so that while he’s sure have a lot to talk about in therapy one day, his parents not taking him to Disney won’t be on the list. Check.

So the first thing I did when we decided to bite the magical bullet was to, naturally, weep over the amount of money we would undoubtedly be spending. Then I asked my friends and coworkers for tips. Which I immediately regretted.

I started hearing words and places and abbreviations I had never imagined; talk of spreadsheets and apps and things like rope drops and park hoppers and magic bands. What?!

Someone said that I would need to choose my meals at least 6 months before the trip. Hold up. You mean to tell me that I have to know what I’m going to want to eat, at a place I’ve never even heard of, SIX MONTHS from now? I don’t even know what fad diet I’ll be on in 6 months, or if I’ll even be alive!

This Disney stuff is next level. I wasn’t prepared for this. Is anyone ever? I had to up my game if I had any hope of finding out where dreams really do come true. There was only one thing to do.

I hired a Disney Planner.

Did you even know this was a thing? I didn’t, but let me tell you this is hands-down the best decision I have made so far and I don’t even want to think about the cluster duck that this whole thing would surely be without her.

Not only has Courtney, my personal Disney princess, I mean planner, answered all 87,000 questions I’ve had so far, but she has gotten up at the crack of Mickey TWICE to nab up my choices for food and events so that, like Sleeping Beauty, I could get a few extra magic hours of my precious sleep. Hiring her ended up saving me time, money, and most importantly, my sanity; and here’s why you may consider doing the same.

The lingo– The first thing that struck me as I began the planning phase of the trip was all the weird Disney jargon and abbreviations; like ADR and cast members, fast pass and memory maker; which at first sounded foreign and annoying but quickly became a part of my everyday vocabulary. Now I’m dropping Disney bombs in random conversation like, “Have a Fantasmic weekend”, in a Minnie Mouse voice. What’s happening to me?

The timelines– If you are like me, I had no idea that there were 4 separate parks. And what that means is that you have to basically study up on which rides and restaurants are at what parks, who has the “Extra Magic Hours”, what the population forecast is supposed to be for each day, what sections are under renovation, and what cycle the moon will be in. It’s freaking mentally exhausting. (Cue Courtney).

My planner provided me with an easy to understand outline of what rides and food joints are in each park, and a list of super secret pro tips you can only get from an expert like her. She’s like a personal genie, but instead of 3 wishes she gave me like 8,000. Courtney will never admit it, but I’m really annoying. Seriously, use a planner. I just can’t stress that enough.

The money– Let’s face it. Disney is not cheap. We could probably go Soarin’ to Jamaica and back for what I’m going to spend in one day at Epcot. And If you think ballgame food is overpriced, wait until you see the price for the food at any Disney park. Has anyone had success with Disney Dine and Dash? Seriously, I considered.

Good thing my girl hooked me up with the dining plan, which is basically like an all-inclusive food and snack package that ensures I’ll gain at least another 20 lbs. I don’t know what the heck a Dole Whip is but it’s on my list and it better be good.

The outfits– Another thing that I can’t quite wrap my head around is all the Disney-themed clothing that seems to be a prerequisite to a day at any park. I don’t know about your family but I’m lucky if the three of us are all even wearing shirts at the same time, let alone custom-made character-coordinated matching family outfits. I could possibly get the kid on board but no amount of pixie dust is gonna convince my husband to jump on this bandwagon and wear a Winnie the Pooh shirt. And do I even want him to??

The characters– When I think of Disney, my mind instantly flashes with visions of oversized ducks, cheerful mice, creepy twin chipmunks, and women dressed like princesses smiling at every turn. Pair that with waiting in super long lines for hugs, and this sounds much closer to my nightmares than any dream I would want to come true.

My own kid said at age 3, “You know the Easter Bunny is just a man in a suit, right?” So at least we are on the same page here, meaning that none of us gives a flying fairy about seeing humans dressed up in furry suits or grown adult women wearing princess crowns to fulfill some sort of prom queen fantasy. So I guess we can scratch this one off the list… (got that Courtney?)

The planning– If you want to do this right, and you don’t have a planner, the truth is that it’s basically a full-time job. “Sorry boss, I can’t come in this week. I’m trying to coordinate our 2019 Disney meals with our outfits. That expense report is gonna have to wait. Do you think Pocahontas likes Italian food?”

If you’re a Disney fanatic and you’ve been recently, you know what I’m talking about. If not, you think I’m flipping crazy. But I basically had to become fluent in spreadsheets in order to maintain some sort of sanity throughout the process before I got my planner involved.

Pro tip- make it a Google Doc and add your Disney planner and boom- instant organizational magic. You can thank me later.

So be smart, and whether you’re a Disney fanatic or a newbie like me, don’t try to do this alone. Its 2018 people. Just call Courtney, her services are totally FREE and you can reach her here.

Everyone keeps telling me that I’ll love Disney World, that there’s no place like it, and that this will be the first of many, many trips there in my future. But I’m not so sure.

I’m gonna make this a 2 part blog series and let you all know how it all goes because so far, the only thing Disney has done for me is to magically drain my bank account.


Lindsay is a full time working mom and wife. She will be looking for side jobs to help pay for this vacation.  



4 thoughts on “Not My Vacation. Part One: Before My First Trip To Disney

  • Lindsey, I understand Courtney is determined to make your trip a special one…even for you! I am her “aunt-in-law” (if there is such a thing). I can help with those shirts if you decide to go that route. 🙂 My sister is taking her grandkids to Disney this year and we made a ton of shirts. Even her husband (grandpa) is wearing them. (We made sure to make his and her grandson’s “male-friendly”.) You can see my work on my FB page under “Kaalee’s Kreations”. Have fun on your trip!!!

  • Wooo!!! That all sounds so exciting! I’m not going to lie though, I don’t get all the Disney hype either. It’s not my cup of tea, but that being said… I’ve never been so who knows, it very well COULD be, I just don’t know it yet!

    A Disney Planner seems to be the way to go! I had nonidea THAT was a thing either!

  • Jane Pesti

    Lindsey!!! Your blog made me laugh so hard this morning!
    A Disney Planner?? Who knew!?? I LOVE it!!!THAT was a good find!!
    My first trip to Disney Land was in my 20’s and I LOVED it!
    Went to Disney World just a few years ago and I loved it again!! It’s bigger and better! A Magical Place like no other!
    Sounds like we will be in Florida at the same time. The weather will be perfect! Not too hot yet! And you’ll even be able to find time for the beach and a well-deserved massage!!! ❤️❤️❤️
    Lincoln, I’m sure, will also LOVE it!!

  • Megan

    I love you and everything you write!! I’m smiling because all this is true! We have Courtney planning ours too🤗There is no way I’d do it any other way!

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