Trip Report Three Teachers Go to Orlando for Disney, I mean a Conference.

I am an artist and educator who has been teaching photography at various levels for the last 15 years. Shamefully I must admit that I am that guy who hides massive portions of himself at work. Well, it turns out two of my coworkers have been doing the same thing. We all love Disney! When a conference opportunity popped up in Orlando we decided to put together a proposal and make it happen. The following are the ramblings and photographs of a somewhat neurodivergent Disney fan.
Inspired by this trip I've created a new Instagram account : https://www.instagram.com/death_metal_disney?igsh=a2VyMzl5MTRjemY4&utm_source=qr

Please follow along!



When: January 10, 2026
Where: 1 Night at AoA
Remainder of trip was spent at the conference hotel, Rosen at the Orange County Convention Center

I am a father of two amazing boys aged 6 and 4. In fact, our first family visit came last July. Despite my wife and I being pretty experienced and passionate Disney fans, that was something new and it hit us in unexpected ways both in raw emotions but also in our perception of WDW is this chapter of our lives.

Back to this trip. We departed school after our last block on Friday and had a smooth ride down to MCO from Boston. I seemingly always miss big security lines and all the messes that you see online. From MCO we hopped into an uber and headed to Art of Animation. This was the first time staying there for the crew. I'll try to avoid being judgemental as we typically stay at deluxe level hotels but the AoA was an interesting experience and kind of perfect for what we needed, a bed and a quick hop to Epcot for our only planned day in the parks.

The conference ran Sunday to Wednesday and I must admit that the idea of bailing one on the workshops for an additional day crossed my mind. Despite the high cost of daily single tickets I was more than willing to do that, more on that later!

Before our Saturday at Epcot, we simply dropped our bags at roughly 645PM, freshened up a bit and headed to Disney Springs. We were amped, fans down in Orlando without families and a reminder of the freedom we all once had. I don't say that in a negative sense towards my family as they are everything in my life but it certainly is not the norm for me anymore. It felt strange having less plans and I wasn't prepared for the lack of chaos over food and what the lads wanted to do. It was absolutely packed at Springs and we stopped for a quick meal at Chicken Guy. It may be my favorite quick spot in all of Disney, bold take!

The vibes were up, just a loads of folks enjoying themselves. We left Boston in a relative "heat wave" of 45 degrees but Orlando was perfect. 70 degrees, I mean how can you complain about that! I was on a mission to snag some gifts for the family and my first stop was at the CoOp for the Drop Factory. My wife was really after some of the mystery Trash Cans. Unfortunately they were sold out and despite my constant mantra of "if you see it and they have it, buy it" I passed on some mystery style LaBubu backpack things. I told myself I'd be back at springs later in the week and I'd get them. Nope, when I returned later in the week they were long sold out. Bad moves! Walking around really set the tone for the trip. We were close to the magic and helped build that anticipation. I can't remember the name of these performers but they were fantastic.

AoA was a bit tricky to navigate with the buildings. We stayed in the Little Mermaid section, the rooms were lightly decorated but were also pretty small. I kept thinking to myself that it would be tough for a family of 4 to spend much time in the room.
We landed back at the hotel around 11PM and quite frankly, we probably overstayed a bit at Springs. Exhausted we stumbled back into bed and off to lala land we went.

Day 1 in the books.

 

[ddbowdoin]

That wrapped up a pretty magical day at EPCOT and really set the tone for the week ahead. Once the conference schedule was in place, we made it a point to do something Disney every day. One night took us to Disney Springs for dinner at Homecomin’, another to Animal Kingdom Lodge for Sanaa, and another to the Polynesian for dinner at Wailulu Bar & Grill, capped off with fireworks at the resort.

Being surrounded by friends and fellow Disney fans made the experience even better. At the same time, it was an emotional trip—spending several days immersed in the Disney atmosphere made me miss my boys. Even at just six and four, they’re huge fans, so they knew exactly where I was, and we didn’t try to hide the Disney side of the trip.

 

[ddbowdoin]

However, there was a surprise headed my way. After an epic day at EPCOT—and a few check-ins with my wife throughout the day—I received a late-night DM letting me know that a Magic Kingdom Extended Evening Hours event was happening while I was there. Normally, we’ve never been an extra-ticketed-events kind of family, largely because the timing of our trips has never lined up with the Halloween or Christmas seasons.


I went back and forth on it. My twenties were defined by a string of questionable financial decisions, and that old FOMO is still very real. As I’ve gotten older—and especially since becoming a father—I’ve grown much more practical with money. I floated the idea to the group and casually mentioned the $189 ticket price. Much to my dismay, Matt #2 immediately said he was in.


By the time I went to bed, I’d made up my mind. I was doing it. Yes, it was expensive, but it was only one ticket—not a family of four.


Bam. Booked.

 

[ddbowdoin]

 

[ddbowdoin]

This was the first time I’d ever seen the Magic Kingdom in its holiday dress. Even in the second week of January, with decorations slowly being stripped away, there was still a quiet power to it. Friends had warned me it wasn’t the full setup, but at night it didn’t matter. What remained glowed—soft, deliberate, almost defiant against the darkness.

Main Street will always own a piece of me. It’s controlled perfection. The music drifts just loud enough to feel intentional, the people-watching feels intimate, and the air carries a strange emotional weight. Families stepping in, full of anticipation. Others drifting out, already preparing to return to reality. Hellos colliding with goodbyes along a stretch of pavement far too small to contain everything it represents.

 

[ddbowdoin]

Despite the event officially running from 10:00 p.m. to 1:00 a.m., I hadn’t realized Disney allowed entry as early as 7:00. After an early dinner at Homecomin’ around 4:30, we lingered at Disney Springs for a bit before taking a bus over to the Contemporary. Around 6:15, we started the short walk to Magic Kingdom.

During that walk, my mind was racing. How was this event actually going to unfold? Was attendance capped? Would it be packed and leave me disappointed? As we turned the corner from the Contemporary walkway, I saw what looked like absolute hordes of people pouring toward the park. A knot of dread set in—were all of these people headed to the event?

We were directed to the far-left entrance, a separate line reserved for the event. It was already full with guests waiting for the 7:00 p.m. entry, and the sight of it did little to calm my nerves.

As it turns out, perception and reality were about to tell two very different stories.

 

[ddbowdoin]

My wife and I have a great travel relationship. We’re both teachers, but we sit on opposite ends of several spectrums. She teaches kindergarten; I teach high school. She’s in public education; I work at a private prep school. On paper, our professional worlds couldn’t look more different.

She often has to pay for classroom materials out of her own pocket, while my school sends me on international trips with students—expenses covered and a stipend on top. There’s nothing quite like spending eight days in Paris and coming home with a little scratch still in your wallet.

Because of these opportunities I’m fortunate to take part in, my wife has turned me into something of a travel tester. The flow of trips—restaurants, public transit, hotels, logistics—gets stress-tested on school travel first. Those experiences then shape how we plan our own trips, refining routes, tightening schedules, and ultimately making our personal travel smoother and more enjoyable.

This Disney trip came with a running checklist—some experiential, some very tangible. There’s nothing quite like waking up to a text that reads, “According to Google, Gideon cookies—if wrapped well—will last at least 3–5 days, so let’s get a good box for home.”

For this trip, and especially tied to the event, my wife was deeply curious about how The Beak and Barrel translates from YouTube to real life. As a massive fan of Oga’s Cantina, I was more than ready for that kind of experience to land inside Magic Kingdom. The moment I booked the event ticket, I started stalking the My Disney Experience app for a Beak and Barrel reservation. Fully booked.

Checked again the next morning—nothing. Lunch—still nothing. One more refresh on the way to Disney Springs around 3:00 p.m. and… there it was. An 8:00 p.m. reservation.

Locked in.

Constant refreshing finally paid off.