My Worst Trip to Walt Disney World Ever

Posted by on September 15, 2020 in Thoughts and Opinions | 0 comments

September 15, 2020

By Caitlin White, Vacation Experience Architect

My last trip to Disney World with my boys was the absolute worst trip to Disney in my entire life. Even though the trip started to feel like a comedy of errors, that’s not how they remember it. Spoiler alert: Even when a trip goes off the rails, it can bond you closer as a family.

While visiting family in Florida last October, we made a day trip to Orlando to go to Mickey’s Not-So-Scary-Halloween party. It was my first trip to Disney after becoming a Wishes Family Travel Concierge Agent and I had been planning that brief trip for months. Halloween costumes that wouldn’t be too hot in the Florida heat, check. Gallon baggies to hold all the trick-or-treating candy, check. Ponchos in case of rain, check. Charged cell phone and backup battery charger for tons of happy family photos, check. I was ready to make some memories! We certainly did-just not the kind I had originally planned on!

Our trip started off great. We spent the day at Disney Springs shopping and having lunch before heading to Magic Kingdom for early entry into the Halloween party. We rode a few rides (Haunted Mansion- my favorite!) and then decided to ride Splash Mountain. My boys were thrilled we were lucky enough to ride in the front row. We, of course, got soaked. My phone was less thrilled with the ride and stopped working because it had gotten so wet. Mistake #1- not putting my phone in plastic baggie or even just my backpack to protect it from water. My plans for taking lots of photos went out the window. (Mistake #2- not purchasing Memory Maker. In hindsight, I should have purchased Memory Maker. I hadn’t because it was “just one day”. I learned my lesson and will always purchase it from now on.)

We spent a few hours trick-or-treating through the park getting so much candy that the gallon baggies I packed were bursting with treats and taking up lots of space in my backpack. We took advantage of the short wait times to ride lots of attractions.  It had started to rain some, but it didn’t slow us down since we had ponchos.  The weather cleared and we did some souvenir shopping. At that point, I was running out of space in my backpack and decided to ditch the ponchos since the rain had passed.

As we exited Space Mountain around 11 pm, the skies opened up. Rain poured down in sheets.  And we began to slog through puddles on the long walk back to the parking lot. The temperature dropped and what had been swelteringly hot was now chilly and uncomfortable. Main Street started to flood with standing water up to our ankles. The boys began to whine. They were tired. They were cold. Why was it raining so hard?! After a long walk and a freezing ferry boat ride, we got back to our car. The boys changed into dry clothes and promptly fell sound asleep. I drove home soaking wet and questioning why I even wanted to go on vacation in the first place. Mistake #3- the rain has never really passed in Florida. Always keep the ponchos.

The next morning, in the light of day and in dry clothing, it didn’t seem quite so bad. It was actually kind of funny. As the boys talked about the trip, they weren’t focused on the bad parts. My youngest talked about how much he loved his “three favorite mountains”- Splash Mountain, Big Thunder Mountain Railroad, and Space Mountain. My oldest was excited for the souvenirs he bought for friends back home. They raved all the trick-or-treating and riding Pirates of the Caribbean with their grandparents and getting to meet Jafar. The rain became a funny story to tell their friends- the amount of rain and their peril at walking through the flooded Main Street getting greater with each retelling. It became something we “survived” together, making us even closer as a family.

Looking back on the trip months later, it isn’t the mistakes I remember (although I will definitely learn from them!). I remember the joy of spending time with my children at Walt Disney World. I remember how important it is to travel and explore as a family. I remember that even when everything seems to be going wrong, we are making memories together. And that makes even a long walk in soaking wet shoes totally worth it.

I would love to help you make memories with your family and plan your next vacation! Contact me at 443-299-9197 for complimentary vacation planning services.
Instagram: caitlin_wishesfamilytravel

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