First trip was in 1999, with my parents and sister, while I was in the third grade. Pre 9/11, you were able to go through airport security without a boarding pass. My mom made up a story about having to travel for work, and we all went to the airport to see her off. As she's about to board her flight, her and my dad let us know that she's not going on a work trip, but that we're going on a vacation to WDW. Hell of a surprise! My first time on a plane AND I'm going to Walt Disney World.
I fell in love with it immediately. We stayed at All-Star Sports, and being a sports obsessed kid, I thought it was the greatest hotel ever built. I remember loving every aspect of the parks, the transportation (I've always been a big fan of trains, so I thought the monorail was the coolest thing in the world), the resorts. It all just felt like I was on a different planet or something. I have no clue if it's because I grew up in hillbilly town or if they've changed since, but the last thing I remember doing was eating Casey's fries on the old bleachers, and thinking they were the greatest thing I ever tasted. I could continue to attempt to wax poetic about the trip, but I'll save you all from that.
When I got back to school, I think my friends stopped hanging out with me for a bit, because I wouldn't shut the hell up about Disney World. Heck, two years later, after "graduating" fifth grade, we had to put together a memory book. One of the sections was to say what you wanted to be when you grew up, and I said either a professional baseball player or an Imagineer hahah. As you can guess, neither one came true.
Well, I was big into sports, and played year round, so it was really tough for my family to find time to vacation. We had about a week stretch between baseball and football, and until about the time I graduated from HS, our family trips consisted of traveling the country and knocking out multiple baseball parks each year. So, I had a long, long break between Disney trips.
Five years ago, my girlfriend and I (now wife), and I were looking for last minute vacation ideas. We both travel for work, and were looking to use some air and hotel points. I'm not sure how or why, but we settled on a short WDW trip. For some reason, we booked it between Christmas and New Year, and to this day I'm not sure why, but we LOVED it. I hate crowds, I hate rude people, I hate waiting, but for some reason that didn't matter to me when I was back in Disney World. We were hooked.
A few months later, work took us out to a conference at the Disneyland Hotel. We loved it there too, and that's when we realized we were the weird Disney adults for sure. I somehow convinced her to make a third Disney trip that year, back to WDW in November, when it would be less crowded and when we could stay for longer. We ended up getting engaged that trip, in front of the castle before the park opened, and were able to enjoy an 11 day "engagement honeymoon". That was our first time staying at Swan & Dolphin (Marriott people), and I ended up falling in love with the Crescent Lake area. There's not much I enjoy more than walking out of IG, after a long post IllumiNations (RIP) stroll around WS, and then taking the long way back around the Boardwalk.
Anyway, as noted, we travel a lot for work, so we ended up going back down again the next year. That's when we decided to become Annual Passholders, which was one of the best decisions we ever made.
Fast forward, our APs just ran out this month, and we decided not to renew them. The "magic" definitely hasn't been lost, but we aren't traveling as much anymore, and just wanted to take a bit of a break. I'll miss it, but this gives us an opportunity to go elsewhere for a bit. They say distance makes the heart grow fonder, and I'm sure that'll be true with WDW. I can't imagine it'll be a long break, but even by taking 1.5-2 years off, there's no doubt I'll be itching to get back.
I've often compared WDW to a PG version of Las Vegas, where the parks/casinos aren't the only draw. I'll always be grateful we had APs for a bit, because it allowed us to not spend all our time in the parks, and to really take in all that WDW has to offer. We spent a lot of afternoons at resort pools, and really got to unwind and relax, which was very different from our first few visits. Again, the magic hasn't faded, but I'm excited to get that "child like" feeling again, after a "significant" break from the World.