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Disney Dreams and Dramas: My Top Unforgettable Moments

Walt Disney World Cinderella Castle
Credit: Disney / Canva Edit

I’m a Walt Disney World Annual Passholder, Disney Vacation Club Member, runDisney participant, and I adore all things Mickey Mouse. For multiple years (before I was old enough even to remember), Disney has been part of my life. And while Disney has changed repeatedly, year after year, one thing remains… the memories.

You know the memories I’m talking about, right? Those magical moments during a visit which seem to be imprinted on your Disney-loving soul. And while ideal experiences would all be positive, sometimes the dreams become dramas. Let’s dive into the dreams and the drama with our top unforgettable Disney moments.

Seven Dwarfs with Jamie and Mike

Credit: Disney Dining

First, the Dreams:

VIP Access Inside EPCOT’s Spaceship Earth

EPCOT’s Spaceship Earth is one of the most iconic Disney park landmarks. The massive “golf ball” (as my kids call it) was formerly sponsored by Siemens. We thankfully had a contact at Siemens that would regularly welcome us into the VIP section of Spaceship Earth, allowing us to relax and peek into the stunning business room that overlooked EPCOT’s former Fountain of Nations in Future World.

Spaceship Earth EPCOT Disney Imagineers Scoff New Designs

Credit: Disney

Free beverages, air conditioning, lounge chairs, and a secret path to skip the line for the Spaceship Earth attraction was a family experience we enjoyed time and time again.

Flag Family at Disney’s Wilderness Lodge Resort

During pre-COVID days, Walt Disney World’s stunning Wilderness Lodge Resort quietly offered resort families the chance to sign up to be a “Flag Family” for the day. This family would arrive in the resort lobby on their scheduled day and help an informative Cast Member raise the flags guests can spot on the resort’s rooftop.

Our family was lucky to be selected. Looking out over the massive Disney property on a resort rooftop is a memory I’ll never forget.

Mickey and Minnie Surprise Hugs

Our family had an early breakfast reservation at Cinderella’s Royal Table. As we left the Main Street, U.S.A. crowd and approached the Cinderella Castle for breakfast, Mickey and Minnie Mouse came walking out from the Castle to do what looked like an early morning photo shoot.

Instead of hurrying by, they stopped us in our tracks and hugged everyone in our 8-person party. From young to old, that 1-2 minute moment with Mickey and Minnie unexpectedly all to ourselves will never be forgotten.

Being in Disney World the Day it Reopened

COVID was a time we’d all like to forget. But, when our family had a chance to be in Disney World on the day of its reopening, we were there. Although there were masks, social distancing rules, plenty of missing attractions, entertainment, and experiences – we had the most AMAZING visit ever.

Parks during COVID

Credit: Disney Dining

Cast Members at Magic Kingdom Park lined Main Street, U.S.A., to wave and welcome guests. They cried. Guests cried. I think we all knew this was finally a step back to normalcy. We walked on rides without waiting. We took photos of the nearly empty park. And for a brief moment in the midst of a pandemic, there was a dose of comfort in knowing things were looking up.

Riding in Walt’s Vehicle at Disneyland

As a child, rides on Dumbo the Flying Elephant or Mad Tea Party’s tea cups may be the highlight of a Disney experience. But, as a self-proclaimed “Disney adult,” I find joy in the moments that seem to be surrounded by pixie dust. Riding in Walt’s car at Disneyland Park (and the last Main Street, U.S.A. vehicle he was pictured in) was a dream come true for this Disney fan.

Alas, the Dramas:

Family Separation

I had a very close family member who was experiencing separation from a long-term relationship. The trip was planned well before the separation, and we were obviously missing a key person in our travel party. While this was one of our most difficult trips to Disney, the drama had moments of joy.

This was the one and only time my family succeeded in pulling the sword out of the stone in Fantasyland at Disney’s Magic Kingdom Park. Yes, we all cried when the sword started sliding out… it’s like Disney knew we needed a winning moment.

Miscarriages and Broken Hearts

I’m blessed with two healthy children who have experienced Disney more times than they can count. Despite their smiles when we mention a Disney trip, anyone who has ever experienced a recent loss or miscarriage knows the pain that can follow when attempting to do something positive.

Jamie and Mike

Credit: Disney Dining

Two different years, two different miscarriages, and I found myself with a broken heart in the middle of the most magical place on earth. I’m not sure what it is, but I swear without saying anything, Cast Members (especially favorites like Mickey Mouse, Minnie Mouse, and Pluto) seem to know how to hold onto a hug a little longer when it’s most needed.

Scarring My Grandmother for Life

I remember visiting Disney’s Animal Kingdom Park, where my grandmother and I were in one of the many gift shops. I knew my grandma was petrified of snakes, so of course, I thought it would be hilarious to ask her to hold on to a rubber snake for me while she was distracted.

“Grandma, can you please hold this?” …. A willing grandma holds out her hands while looking at something else…. It didn’t take her long to look down at her hands…. And the next thing you know, the Disney gift shop is filled with blood-curdling screams from my sweet grandmother and a rubber snake being chucked through the air. Sorry, Grandma (and sorry to the Cast Members who were not pleased)!

Getting Caught in the Rain

Caught in the rain on a tram at Disney

Credit: Disney Dining

It’s Florida, people! If you don’t prepare for rain when visiting Walt Disney World Resort, well, you’re going to be very disappointed. That said, getting caught in the rain is no fun – especially with a dramatic husband and child. We’ve been caught in the rain numerous times, but for some reason, one tram ride in a torrential downpour was memorable as rain blew in from all directions. As you can see in the picture, my daughter and I thought it was hilarious… my husband and son… not so much.

Dreams and Dramas

While I’ve only listed a few dreams and a few dramas, the list could go on and on. I think the takeaway from our many Disney trips is that whether it’s a day trip, a two-week vacation, or simply a quick two-hour meal, there are going to be those positive and negative moments.

Kids at Disney

Credit: Disney Dining

Yes, I miss the free FastPass+, Disney’s Magical Express, and an affordable Disney Dining Plan, and I have those same woes many Disney fans have had or are experiencing now. But, at the end of the day, when I think about Disney, those not-so-great dramas are quickly forgotten or brought into a positive light when I think of the many memories that make Disney feel like home.

What are your top unforgettable Disney moments? Let us know in the comments!

The opinions expressed in this article are the author’s own and may not reflect the views of Disney Dining as a whole.

About Jamie Sylvester

I'm a Disney nerd! A kid at heart who loves the magic and memories of Walt Disney World. I follow all things Disney and enjoy the vacations, day trips, weekend getaways, and geek out over the planning of such events. My goal is to experience as many Disney desserts and cocktails as possible! Married to another Disney nerd and blessed with a daughter and son, we thoroughly enjoy the magic at Disney and are here to help others experience the magic as well.