Ten People, One Dream, and a Whole Lot of Disney Magic!
At our Christmas Eve dinner in 2011, I shared an idea that had been quietly sitting in my heart for a while: a big family trip to Walt Disney World. We’d never gone on a big family vacation like this before, as my parents couldn’t afford to take us on trips like this during our childhood. So, I came prepared with posters of the different resorts, park maps, and dining options. I laid it all out like a dream board at the dinner table and made my pitch to my two sisters, their partners, and my parents.
This was important to me as we were still navigating the heartbreak of losing my younger daughter. I wanted something that would help us reconnect, lift our spirits, and bring smiles to our faces again. My older daughter and niece were seven and five then, a perfect age for meeting your favourite Disney characters and experiencing the magic.
I’ve always loved Disney and dreamed of a multi-generational trip that would bring us all together in a joyful, unforgettable way. This was the perfect time for such a trip.
The Planning Begins
I dove into the planning in the new year and quickly became overwhelmed. Ten people and ten different needs. My mom was recovering from knee surgery and needed accommodations for mobility. My older sister and her husband didn’t have kids yet, so I wanted to ensure something for everyone.
Trying to plan every detail, from resorts to tickets to dining to flights, quickly became a lot. That’s when someone suggested a Travel Advisor. Honestly, that changed everything.
She handled the entire booking. We stayed at Port Orleans French Quarter and scored a free dining promotion. She organized all four park tickets with park hopper access and ensured we had tickets to Mickey’s Very Merry Christmas Party. Every detail, from dining reservations to park logistics, was handled.
She made us a chart showing which parks we’d visit each day and where we’d eat. She also gave us great tips, like booking breakfast at Crystal Palace before Magic Kingdom opened, which allowed us to enter the park earlier. She even helped us navigate the old FastPass system.
The Journey There
We managed to get all ten of us on the same flight, but it was a late one, 11:30 p.m. into Orlando. By the time we got through customs, it was midnight. The Magical Express wasn’t running that late, so we stayed at a hotel near the airport. The next morning, everyone was a little bleary-eyed as we boarded the Magic Bus to get to our resort.
Once we arrived at Port Orleans, we could finally exhale. The resort was lovely. After dropping off our bags, we took the boat to Disney Springs for lunch. We had our first character meal at Mickey’s Backyard BBQ that evening. Getting there involved a bus and boat ride, but it was all part of the fun.
That First Walk Down Main Street
The next morning, we headed to Magic Kingdom. This moment still lives in my heart. Walking onto Main Street with music playing, cast members waving, and characters fully in the moment, didn’t feel like just another theme park. It was like stepping inside a storybook. I saw it on everyone’s face. Something shifted. We weren’t just tourists anymore. We were part of the magic.
The Disney Magic for Every Generation
As the days passed, we explored all four parks, each offering something special. What stayed with me most wasn’t just the attractions. It was watching everyone, from my parents to my sisters to the kids, discover their version of Disney magic.
My parents smiled more than I’d seen in a long time. My daughter and niece were wide-eyed with wonder. My sister and brother-in-law, who didn’t have kids yet, fully embraced the fun. Everyone found their place in the magic. Everyone’s inner child came alive.
Some days we split up, each doing our own thing before meeting again for dinner or a character meal. Those reunions, sharing stories over food, showing photos, and laughing, were just as special as the parks.
A Memory That Lasts
That trip became a core memory for all of us. It was more than a vacation. It was a healing, joyful, bonding experience. It reminded me how powerful travel can be when it’s about more than just the destination.
In 2023, we returned. This time, it was my sisters and our kids. My older sister was now a mom herself. We spent ten amazing days reliving old memories and creating new ones. Watching our children re-experience the magic we’d once seen through their eyes was unforgettable.
There’s just something about Disney. It invites you to play again, to feel again. For our family, it gave us a moment to pause, reconnect, and carry joy forward.
If you’re thinking about planning your first Disney trip with your family, and it feels like a lot... I get it. I remember how overwhelming it was to figure everything out and make it memorable for everyone. That’s why I put together a simple free planning guide to help take the pressure off.
It’s filled with tips I wish I had when I started: a few timelines, some dining suggestions, and ideas to make things smoother along the way.
Your first Disney trip shouldn’t be stressful; it should be full of moments your family will talk about for years. If that sounds helpful, you can download it here.