Winging it (Or “Why I’m not actually making plans for my upcoming WDW trip”)

I’m a planner by nature. Whether it’s school, work, or vacations, I have every single detail handwritten in list form in my planner. Generally, things are color-coded. I have to have every detail written down or my anxiety tells me I’ll miss something. My lists have lists.

Usually when I go to Disney World, I have an extensive, organized itinerary. I spend up to a month before-hand planning which park we’ll go to on which day (based on which parks have EMH, because we stay off-property and try to avoid EMH crowds), and which restaurants we’ll eat at, and what our Fastpass+s will be, etc.

MyDisneyExperience, the (relatively) new Disney planning app, has made this a breeze. By pre-planning FP+s and dining reservations, we can create a fully scheduled day easily.

However, when I was on my Disney College Program last year, I got to learn the importance of “winging it,” or going to a park with no set plan in mind. And it was great. I kind of loved waking up on a day off and saying, “I want to go to (insert park name) today!”

Since I left WDW in August of 2014, I’ve been back four times. In October, I went with friends, and while we had somewhat of a schedule (we had to figure out which parks to do when because we were using specific convention tickets that were only good at certain parks), we were fairly spontaneous in our activities. 

In November and January, I went with my family, and, as usual, we planned out every detail of every day. It kept everyone on track, which was especially nice in January when we had a party of 7. MyDisneyExperience was a lifesaver, and every morning before we left the house, I’d read off exactly what we had planned — FP+ times, dining reservations, etc.

In March, I went to WDW with my mom, sister, and a friend from college. I kept saying I was going to wing it, but about a month before the trip I put together an itinerary to make it easier on my mom, who could only come for a few days and still wanted to do everything. Before I knew it, yet again, every detail was planned out. My sister and I even scheduled in a “winging it” day, our last day, and as soon as she arrived in WDW we ended up planning out that day, too.

Planning is important. Especially if you’re an obsessive organizer like me. But again, on my DCP I learned the importance of “winging it,” too.

My next trip is June 4-10. I started making the plans for this trip back in early March, as soon as I found out that my best friend and CP roommate, Nichol, got accepted to do the Summer Alumni DCP. As soon as I found out her program dates and looked up the dates of my summer course, I picked a week and booked my flight. However, I soon realized that I would not be planning every single detail of the trip. In fact, 20 days out, I’ve only booked my flight, my hotel (Pop Century), and one dining reservation — lunch at Be Our Guest on June 5th (because it was available and why not?). 

So what makes this trip different? Why am I not obsessively planning every detail? Plain and simple — Nichol doesn’t have her work schedule yet. And since this trip is for me to visit her (and visit WDW), I don’t want to make set plans until we know what days and hours she’ll have off. 

We have noted a few things that we know we want to do as soon as we have her schedule — spend as much time as possible at Epcot, go see La Nouba (shoutout to a former coworker and good friend of mine for offering us her lightbooth seats), and (if we can) go to Ohana one night. We also want to explore resorts, walk the World Showcase before it fully opens, check out the new Downtown Disney offerings, and watch Wishes/Illuminations/Fantasmic as much as possible. But none of these have a specific date yet, and probably won’t until I actually get there. And even though I love planning, I’m actually enjoying NOT planning this trip. It’s interesting not knowing what I’ll do when I get there (though I’ll likely drop my stuff at the hotel and go straight to Downtown Disney, as usual!).

I’m fortunate enough to be an annual passholder, and to have spent enough time at WDW, especially over the past year and a half, that I don’t feel like I have to do EVERYTHING on each trip. However, I’m already planning my next-next trip for the fall (and then hopefully my next-next-next trip will be for a job interview next spring). I’m excited to (hopefully) make Orlando my forever home next year, and be able to “wing it” in the parks whenever I want. 

Like I said, planning is my thing.

Even though I may not be planning each detail of this trip, I do have my packing list done…

And even though I don’t leave for another 20 days, I’ve already got stuff in my suitcase.

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2 thoughts on “Winging it (Or “Why I’m not actually making plans for my upcoming WDW trip”)

  1. Rosemarie S. says:

    I so agree! I have just begun packing for my July trip (not to Disney, unfortunately) And the first time I ever went to Disney I read one of those “Disney World for Dummies” books cover to cover before going. My friend wanted to “wing it” but I knew that it was too big and we would see nothing if we did it her way. Planning is good – very good! 🙂

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