Your cart is currently empty!
Prologue – Planning ✈️
If there’s one thing I love, it’s planning. Trips especially. I always have a dozen itineraries tucked away—some lived, some still waiting, and some crafted for other people entirely. (Like our couple friends’ honeymoon in Ireland? Yeah, I planned that.)
So when it came time for our first big Disney trip—my first visit as an adult, his first ever—I was giddy. I remember sitting at work, headset on, pretending to talk to insurance companies while secretly scrambling for last-minute dining reservations. And somehow, I got them. The thrill of snagging Cinderella’s Royal Table felt like a personal victory spell.
We opened our first big credit card for this trip: a Disney Chase Visa with a $4,000 limit, and yes, I used every single penny (Chase, take me back 😭). I stalked airfare daily until I figured out that Cleveland, even with an overnight hotel and parking, was cheaper than flying out locally. So, Cleveland it was.
Disney made the whole thing feel easy—and expensive. I squealed when our vacation box arrived, complete with MagicBands and glossy pamphlets for our resort. It felt like a prophecy delivered by mail.
We wanted to do it all. And despite being overweight, footsore, and averaging about four hours of sleep a night, we did it all. First bus out in the morning, last bus back at night.
Of course, we weren’t as travel-savvy back then. We hired limo services instead of trying rideshares, and we thought shipping distilled water for his CPAP to the hotel was smart—until it arrived exploded. Rather than just hopping in an Uber to Walmart, we panic-ordered pharmacy delivery. Rookie mistakes, but at the time, it all felt like part of the chaotic magic of a first big trip.
October 3 – Arrival Day 🚌
Orlando quickly became our third most-visited airport (with Detroit as our home base and Chicago still holding strong at number two). From the moment we landed, we followed the signs for the Disney’s Magical Express (RIP)—Disney’s free bus service that whisked resort guests from the airport straight to their hotels. The moment you boarded, you were already inside the bubble. They even played a welcome video during the thirty-minute ride, designed to hype you up before you’d even seen a castle spire.
Our stop was Port Orleans – Riverside, a resort styled after an old-fashioned southern riverfront. But we didn’t even settle in. Instead, we hopped straight onto the hotel’s riverboat to Disney Springs (which I still called Downtown Disney at the time). Floating along the Sassagoula River, we passed the famous amphicars—those retro convertibles that literally drive into the water and become boats.
Our first destination? Disney Quest (RIP). It was an interactive, wand-waving adventure experience where you carried a magic wand that triggered effects throughout the building—treasure chests opened, crystals glowed, runes lit up. It was very “Disney adults playing D&D-lite in public,” and I loved every second.
It was also where we picked up our bride and groom Mickey Mouse ears. My ex-husband had proposed a few months earlier, and this felt like our first newly-engaged souvenir. Corny? Yes. Magical? Also yes.
October 4 – Islands of Adventure 🦖✨🪄
Our first limo ride (because Uber was still in its “stranger danger” era) took us to Universal’s Islands of Adventure, and we spent most of the morning darting between shade and splash zones to survive the Florida heat. The Jurassic Park area became our refuge—towering gates, jungle pathways, and a water ride with no line where you could cool down in seconds.
But the real reason we came was The Wizarding World of Harry Potter. This side of the park had the iconic Hogwarts Castle, and even though we were too overweight to ride the attractions, we still got to walk the castle. Stained glass glowing, talking portraits on the walls, Dumbledore’s office brought to life—it felt like stepping straight into the books.
We bought wands and joined in on the interactive spell adventure, tracing runes in the air and watching shop windows spring to life. We downed more frozen butterbeer than I’ll admit publicly and ate at the Three Broomsticks, complete with rustic beams and hearty wizarding meals that made you feel like you’d stumbled into the Leaky Cauldron. Outside, we caught a performance from the Beauxbatons girls and listened to the Hogwarts Choir sing.
Somewhere between all the magic, I picked up a Dobby doll for an old coworker’s daughter who had just discovered Harry Potter.
We wrapped the night back at Disney Springs with dinner at the T-Rex restaurant—basically the dinosaur version of Rainforest Café, complete with meteor showers and animatronic giants. Looking back, my daughter who’s obsessed with dinosaurs now would absolutely lose her mind there.
October 5 – Universal Studios Florida 🎬🧟♂️💍
By day three, our feet were killing us. We limped our way into Universal Studios Florida, telling ourselves we were there for Harry Potter but stopping every chance we got to rest along the way.
We caught the Graveyard Mashup, a campy rock show where Dracula, Frankenstein, and other Halloween monsters performed while Beetlejuice himself played MC. He actually came into the crowd, noticed my engagement ring (thanks to those celebratory buttons), and made a big fuss about it.
✨ Travel Tip: At both Disney and Universal, you can stop by Guest Services and grab a free button to mark special occasions—birthdays, anniversaries, engagements, first visits. Cast Members and performers often notice them and will go out of their way to add a little extra magic to your day.
We also stopped for photos in the Jaws section, met SpongeBob and Patrick, and rode the E.T. Adventure—which still smells like childhood. The park was decked out with décor for Halloween Horror Nights, Universal’s separately ticketed evening event with haunted houses, scare zones, and live entertainment. Even in daylight, you could feel the spooky energy creeping in.
Then it was on to Diagon Alley. We ate at the Leaky Cauldron, explored Weasleys’ Wizard Wheezes, got lost down Knockturn Alley, and stopped for a photo with the Knight Bus, its driver, and the wisecracking shrunken head who accused me of being a Death Eater because I had a skull on my tank top. 😂
We returned to Disney Springs that evening to eat at Planet Hollywood. Somewhere I was excited to return to having remembered eating there when I was younger but was, unfortunately, not as impressed as an adult.
October 6 – Animal Kingdom & Magic Kingdom 🦁🏰🌺
This was our park-hopping marathon day, bouncing between kingdoms like we were trying to squeeze a week’s worth of magic into twenty-four hours.
We started the morning on the Animal Kingdom safari tour, rumbling through the savanna in an open-air truck. Halfway in, our driver had to stop because a group of giraffes decided to camp right on the trail. They weren’t in any rush, and honestly? Neither were we.
After wandering the shaded trails and marveling at the Tree of Life, we headed off to Magic Kingdom for our coveted lunch reservation at Be Our Guest inside the Beast’s castle. Back then, this was the impossible booking—and somehow, I had snagged it.
In the afternoon, we circled back to Animal Kingdom for the Finding Nemo musical, then took the train to Rafiki’s Planet Watch, where we met Rafiki, Chip, and Dale.
We closed the day with the Spirit of Aloha Dinner Show at the Polynesian Resort. It wasn’t just dinner—it was a full luau-style performance with hula dancers, fire twirlers, and island music woven between courses of tropical flavors. At the time, it felt like the perfect finale to a long day. Looking back, it also felt like a whisper of our future—a little bit of Hawaii foreshadowing the honeymoon we’d take on the real islands not long after.
October 7 – Epcot & the Food & Wine Festival 🍷🌍
We spent this day deep in Epcot’s Food & Wine Festival—that annual event where the park becomes a tasting buffet of global flavors, food booths pop up around World Showcase, and you sip your way across countries like a slightly tipsy diplomat.
At the Rose & Crown Pub, we met the sweetest waitress named Amy from Scotland. She told us stories about her mum, laughed with us, and made us feel like we’d wandered into a local pub back home. We tipped her 100% and called management to sing her praises.
Later, we caught the Eat to the Beat concert featuring Smash Mouth (RIP Steve Harwell, 1967–2023). The crowd sang along to “All Star” like it was a hymn of our generation.
We finished the night with IllumiNations: Reflections of Earth, Epcot’s grand fireworks and fountain show celebrating our planet in three movements. It was one of those nights where the air smelled like wine and fireworks, and everything felt whole.
October 8 – Hollywood Studios 🎬🌙
By this day, my period showed up uninvited. Because that’s just how women’s bodies roll—right in the middle of magic and adrenaline. But I refused to let it steal the day.
We met Donald and Daisy (my sister’s favorites), posed on Hollywood Boulevard, and explored the beginnings of Galaxy’s Edge—just a gift shop called Tatooine Traders and one ride, but still exciting.
Lunch was at Mama Melrose’s Ristorante Italiano—good, but heavy—and afterward we realized there was a Pizza Planet, which would’ve been way more fun (and easier on the stomach).
We also racked up the most PhotoPass pictures here. (For the uninitiated, PhotoPass is Disney’s in-park photography service where professional photographers capture your moments so you can actually both be in the photo for once.)
And because sometimes love looks like doing the thing you dread, I went on Tower of Terror and Rock ’n’ Roller Coaster—both of which I loathe. I hate heights, drops, and going upside down, but I did it for him. He was thrilled; I was proud of myself for surviving.
We caught a Beauty and the Beast stage show, wandered through the golden-hour glow of the park, and ended the night with Fantasmic!, a mix of water, fireworks, and Disney dreams.
October 9 – Magic Kingdom 🎠🎃✨
Our final day started slower. We had a later breakfast reservation, so we finally took time to wander Port Orleans – Riverside, the resort that had quietly been our home all week. It felt good to notice the details we’d been too busy to appreciate before—the water wheels, the bridges, the way the morning light hit the river.
Then we headed to the Contemporary Resort for breakfast at Chef Mickey’s, where the characters make their rounds between pancakes and coffee refills. After that, it was off to the Magic Kingdom.
We met Tinker Bell, Woody, and Jessie, then—of course—made a beeline to The Haunted Mansion and Pirates of the Caribbean. Afterward, we met Peter Pan, floated through It’s a Small World, and somewhere along the way I realized my autograph book was gone. Between the exhaustion and my period hormones, I was devastated. A kid probably picked it up, and I hope they loved it.
We caught the parade, got caught in the rain (classic Florida), and returned later that evening for Mickey’s Not-So-Scary Halloween Party. We got PhotoPass pictures with ghostly magic, watched the Hocus Pocus Villain Spelltacular, and sang along to the Boo-To-You Parade, surrounded by families dreaming of future trips with their kids.
October 10 – Departure Day ✨🏰✈️
Before heading home, we had one last royal sendoff: breakfast inside Cinderella’s Castle. The park hadn’t even opened yet, so walking down Main Street in the quiet morning light felt like trespassing in a dream. Inside the castle, we dined beneath vaulted ceilings and stained glass windows, greeted by Cinderella herself.
After breakfast, it was time to face reality. We returned to Port Orleans – Riverside, picked up our luggage, and boarded the Disney’s Magical Express for the airport. The ride back was quieter—no hype video this time. Just the hum of the road and the ache of leaving a little world behind.
We ended up re-visiting several times after that for various reasons that will appear in future Travel Thursday posts. Disney runs in this witch’s blood. 🖤✨
Leave a Reply