Disney Nannying: The First Day

If you’ve never experienced waking up at 3:30 to wrangle three to six boys into a two hour car ride to an airport that will take you another two hours to a bus ride that will take you a half an hour to another bus that will then take you to Disney’s The Magic Kingdom (only half an hour back in the direction you started from, effectively canceling the first bus ride), I advise you never to try it. Instead, experience Disney World as it was meant to be experienced, via your own private helicopter.

But lacking a private helicopter, on Monday I wrangled three to six boys (and two parents, for a total party of six to nine people) into Disney World the old fashioned way.


Very bland picture snapped over the head of a child on the bus from the airport to the resort. I was mostly interested in the palm trees. Palm trees!

I’d never been to Disney World. I’d been to Disneyland back in 2007, and I don’t remember much of it besides dragging my poor grandfather on the Indiana Jones ride approximately thirty times. I was at an age where meeting characters was highly embarrassing, and I don’t recall much of my experience besides some admittedly nice snippets of pirates and jungles.

Pulling up to Disney’s Boardwalk Resort was a surprise. I was going into this place blind. Not only did I know little about the park itself, but I had no idea where we were staying.


Hey, this place is pretty nice.


…Hey, this place is REALLY nice.

Stepping into the Boardwalk hotel was everything I expected of a place for rich people to stay. I went back and forth in my head for quite a while about how ritzy it really was. Did it just look ritzy because it was Disney and Disney has high standards? Or was this actually where the elite stayed? The rooms themselves were not overly remarkable, but the hotel and its surroundings were magnificent.


It had multiple chandeliers in the front lobby. It really only takes one chandelier for a place to be out of my league.

I thought about this for a very long time before I remembered I had a smart phone and looked it up. ~$500 a room per night. Two rooms for the employer/nanny party (they all packed into one and let me have my own). Five nights. (For those who can’t do math properly, this is around $178,000 for the total stay.)


It’s a lot fancier than the hotel I used to work at. For a start, this one leaves you chocolate. On your bed! CHOCOLATE! You can keep it and everything, and they bring you MORE.

At this point, it was back into the bus to head to The Magic Kingdom. The boys squabbled. The parents stressed. I was conflicted because I had at that point been working eight hours and it was barely noon, but on the other hand, Disney.

(I note here that people often think I’m younger than I am and I frequently get mistaken as the oldest child of The Family I work for. On the way through the gates, the cheerful Cast Member directed me to scan my Magic Band by way of saying “Over here please, Princess.” Guess what nickname will follow me for the rest of my life.)


After subjecting the poor security people to my endlessly deep nanny bag (I swear I don’t have a gun under all these Wet Ones), we shuffled through to the main entrance. While the whole family stopped to line up and pretend they were happy and relaxed for a Disney photographer, I got a quick picture of the clock on top of the train station.

It was at this point that I also realized I would never get an actually decent picture at Disney World, because I had no time to do anything but follow closely and herd children. All pictures seen here are the result of me holding up my phone and running sideways to stop a small boy from obliviously following the wrong family.


Also, this was “Jersey Week,” when the entire population of New Jersey and six or seven of their closest relations attend Disney World while school is out. There would never not be a crowd in my pictures.

It quickly became clear that none of us had any idea what we were doing, where we were going, or even what we would like to do. I say “we” here, but I was working so I had as much say in the matter as the next random stranger on the street. Vacations with the family can be slightly stressful due to the high pressure to relax.

(And the fourteen hour days.)

We had a few Fast Passes under our belt, but even then that didn’t give us much direction. After stopping to pick up some lunch, we blundered our way down various confusing streets and ended up at one of the places I clearly remember from my California experience.


Because you can never, ever forget it.

Predictably, the eldest boy hated it because it had dolls, and they were dancing, and they were singing, and they had dresses on, and it was girly. Hatred of everything would become a recurring theme on this trip.

To make up for dragging Grumpy through The Worst Most Embarrassing Ride Ever, we split our group by age and I accompanied Mr. Parent and the few older boys to Space Mountain, which fortunately did not feature dolls or girls.


We did not have a Fast Pass for this ride. This is mostly what I remember of it. There was about an hour and a half of this.

When you finally reach the end of the line in Space Mountain you’re loaded into a line of single-seat cars and shot off in the dark through a series of sharp twists, turns, and dips. It would have been more thrilling if I hadn’t been approaching a “working thirteen hours” headache, and I came away with the conclusion that it wasn’t really worth spending an hour and a half in line for.


Picture of the thrilling interior of Space Mountain.

Naturally, when we stepped off the cars the very first thing out of the boys’ mouths was “CAN WE GO AGAIN?!” as though waiting in line was not a real thing.

But by the time we got out, it was dark, and we had dinner reservations approaching, so we hustled out of Tomorrowland and headed back for the buses. We had managed a whole two rides that day, which was a rousing success with six to nine people to keep track of in Jersey Week.


But the thing was… even though I had been working sixteen hours at that point, even though the boys had not stopped squabbling once, even though this vacation (like many past vacations) only served to stress The Family out more… it was magical. Every bit of it. All the waiting in line and the crowds and the brief glimpses of princesses from afar. Seeing that ridiculous, lovely castle lit up under all the “snow” was outrageously beautiful.

Sure, it wasn’t my vacation. I was there to do a job, and nannying with the parents there is doubly difficult, and it was hot and tense and a little bit awful at times. But that first mangled half day was still strangely wonderful.

Leave it to Walt Disney World to make my day so conflicting.


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