One of the long-running tasks on my to-do list is figuring out exactly how many times I’ve visited Walt Disney World. The childhood trips mostly roll into each other, so I need to sit down with my parents and figure out the chronology. This is definitely not a complaint; the fact that I even have this task reminds me how lucky I was. The long car trips to Florida from Missouri did not happen every summer, but they were frequent. I’ve continued that legacy with my girls, though we’ve realized that flying (when it’s feasible) might be a better choice for us on vacations.
I’ve been looking back at old photos lately and thinking about the fun of those childhood vacations. It was definitely a different era, especially before the resort expanded in the ’90s. As I compiled this list of my top Disney World vacations, certain memories stood out from the rest. The recent family trips as an adult are clearer, but moments remain in my mind from earlier visits. There have been good times on each of our vacations, so this was not an easy list to compile.
It would be easy to include our most recent vacation in January, which was a blast. We took a slower pace, and that approach made the parks seem less daunting. It’s a telling reminder that I’m not ranking these vacations based on how many attractions we did. The choice is more about the whole experience, where I was in life, and the resort’s total offerings. I hope you enjoy this look back at some of my favorite memories from four decades of Disney World vacations.
5. January 2012 (Best Off-site Visit)
My older daughter Elise was born in April 2009, and I started planning her first trip in my mind very early. We waited a while (relatively speaking for an avid Disney fan) and took her in January 2011. It was a fun trip overall, and we stayed at a solid off-site condo. She was a little too young to enjoy it, however. I’m not criticizing any parents that take their kids that young and earlier; it just wasn’t the best for her. One year later, we returned when she was just shy of three years old. We also traveled with my wife’s parents, which provided some extra support.
There were quite a few changes on this trip from the previous year. We adjusted to traveling with a child; it’s an entirely different experience. We also stayed at a massive off-site condo at the Grand Beach that worked perfectly for the group of five. When fans cite the benefits of staying outside the bubble, I can definitely understand. The space of a three-bedroom unit and the convenience of a full kitchen helped so much.
Along with visits to all four parks, we also spent a day at Universal Orlando to see the Wizarding World of Harry Potter. Despite the lack of many attractions for a two-year-old, it was worth it to experience that stunning land. We also spent a day at the Canaveral National Seashore, which is a gorgeous way to escape the masses. It’s only about a 90-minute drive from Orlando and a pleasant change of pace from the parks. Everything just fell into place in this trip.
4. May 1998 (End of Early EPCOT Center)
During my college years, my interest in theme parks fell by the wayside. I still thought about Disney World, but there were too many competing priorities. Even so, it sounded like a great idea to take a trip to Florida after graduation with my brother and his girlfriend. It was the first time I’d visited the parks apart from a family vacation, so it all felt different. In hindsight, this era also included the last gasps of EPCOT Center.
We weren’t rolling in money, so we stayed at a nearby Days Inn and drove to the parks. We also spent a lot of time at Pleasure Island, which was still popular. The revelation was the Adventurer’s Club; I knew nothing about it until we visited. We also enjoyed the Comedy Warehouse, which felt different from typical Disney entertainment. Disney Springs is nice, but it still lacks the charms of these two spots.
Another benefit of this vacation was getting a final chance to experience Horizons and the original Journey Into Imagination. Both would close within the year, and their replacements fell short. I didn’t realize how lucky we were to see them at the time. Future World also still included Wonders of Life, The Living Seas with the Sea Cabs, and Food Rocks. All of these attractions would be gone by the next time I visited the parks. We visited less than a month after the opening of Disney’s Animal Kingdom, so it was cool to explore an entirely new theme park. We also spent a lot of time at the Disney/MGM Studios enjoying attractions like the Tower of Terror.
3. June 1984 (First Trip to EPCOT Center)
The Tomorrow Society (and my Disney fandom) would likely not exist without EPCOT Center. The Magic Kingdom is a wonderful park, but experiencing Disney World’s second park made the biggest impression. I still have clear memories of my first trip to EPCOT Center in the summer of 1984. We first walked into Spaceship Earth, and I had no clue what was coming. The opening scene of the cavemen was ominous and a little frightening, but I was hooked.
I have no memories of where we stayed on this trip; it could have been anywhere. What I do remember is the wonder of visiting the World of Motion, Horizons, Journey Into Imagination, and Spaceship Earth. I’ve never lost that feeling and still have goosebumps every time we stroll up to the massive geodesic dome today. Epcot may not match its early days, but there’s still real power in those first moments walking into Future World. They changed my life for the better.
2. January 2016 (Holiday Weekend Trip)
We’ve been extremely lucky to take our girls to Disney World regularly since that first 2011 trip. My younger daughter Etta was born in March 2013, and her first trip happened in 2015. We stayed at the Grand Beach again, but the resort was showing its age. The drive down to Florida also had more traffic and took its toll. For our next trip the following year, we decided to change up our typical Disney vacation.
The first step was deciding on the length; one week is a long time when traveling with kids. The girls were in school, so taking them out for a week in January was no longer possible. We also decided to fly due to the shorter time and stay on site at a Disney resort. I hadn’t stayed on site at anything but Pop Century since the early ‘90s, so this was a big change. We found a good deal at the Animal Kingdom Lodge, and the rest is history. I’ve been hooked on that resort (and staying on site) ever since. This vacation was a game changer for me in many ways.
I discovered that three park days was perfect for a family trip, and two days at The Magic Kingdom gave us more time for secondary attractions. We also just lucked out with mild temperatures, manageable crowds, and even with the buses. This was my final viewing of the Main Street Electrical Parade, and we lucked into a close spot in Liberty Square. Everything just clicked, and it will be hard to recreate the magic again.
1. January 2005 (Empty Disney World)
Following the post-graduation trip in 1998, I didn’t visit Disney World again for nearly seven years. Exiting college with a journalism degree, I had limited funds and traveled with friends that didn’t care about Disney. I’m not sure why, but I randomly picked up an Unofficial Guide in late 2004 to become reacquainted with the parks. My girlfriend Erin (who I later married) hadn’t visited since she was young and thought it would be fun. The result spoiled me for all future trips in terms of prices and crowds.
We booked a room at the Pop Century (which was still fairly new) for $53 a night. Disney was still recovering from 9/11 and offered crazy deals at the time. Airfare and tickets were still very reasonable, and a vacation didn’t break the bank like today. The resort and the parks were ghost towns, and that allowed us to see everything repeatedly over five days. I’d never ridden Test Track, Rock ‘n’ Roller Coaster, or Buzz Lightyear before this trip. I lost at Buzz Lightyear repeatedly to Erin (I still do), which I was able to do because queues were empty. Even popular attractions had no waits, and we experienced the parks without any congestion.
These were also the days before the rise of the Disney Dining Plan, so eating at a place like Le Cellier was truly something. I know that what I’m describing sounds too good to be true, but it’s an accurate description. Paper FastPass was available, but we rarely needed it. Disney had yet to figure out how to capitalize on the international market, so it was mostly adults without kids visiting in January. I doubt we’ll ever see Walt Disney World in this state again. It was amazing.
Related Articles – Disney Vacations
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Tomorrow Society Podcast, Episode 37: My Disney World Trip Report
Disney’s Animal Kingdom Lodge Review, January 2016
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