I Took a Dream Vacation to Disney World With My Twin Teen Sons



  • I planned a trip to Disney World with my twins when they were 13, but it was canceled three times.
  • It was our first vacation with just the three of us.
  • I was worried that as 16-year-olds, they would be too cool for Disney — but they loved it.

In 2018 when my twin sons were 11, my wife and I took them to Disneyland. They loved taking in the characters, the shows, the rides, and the food. They ended the day in matching Disney T-shirts and Goofy hats — we’d created Disney fans for life.

At least, that’s what I’d hoped. 

As a theme-park enthusiast, when thinking about our next trip, I decided I wanted to spend a week in Orlando, Florida, and go to Disney World — in those seven days, I planned to go to six theme parks. While this would be an ideal vacation for me, my wife had set a personal limit of two theme-park visits a year. She told me to go ahead and book the trip for me and our sons without her; it would be a boys’ trip. 

So at the end of 2019, I booked the trip for September 2020 for myself and my two boys, Charlie and Thomas.

Three years after I first started planning, we finally got to go on our dream Disney vacation

Unfortunately, due to COVID, we were forced to cancel and reschedule this trip three times. During this period, the boys matured, and when we were finally all set to make the trek from Melbourne, Australia, to Orlando, Florida, for our long-awaited vacation in September 2022, they were 16. By then they were taller than me, had started shaving, and were more interested in girls than cartoon characters. 

I asked them if they wanted to cancel the Disney trip and take our boys’ trip elsewhere. 

As I awaited their answer, I held my breath, hoping they would say, “No.”

“Of course, we still want to go, Dad! We love Disney!” Charlie said with far more gusto than I could have hoped for. Thomas nodded enthusiastically; the trip was still on. I had never been happier.

Waking up early was hard for the boys, but a crucial step to taking advantage of the parks

Since our previous Disney trip, the boys’ routines had also evolved. Back in 2018, they were always up bright and early, ready to tackle the day with the enthusiasm of kids in a candy store — which, I guess, in many ways, they were.

Now they rarely get out of bed before noon unless it is a school day. They’ve fallen into a routine of staying up late and waking up for breakfast as I’m eating lunch. While this laziness is OK at home on the weekends, the key to making the most of a Disney vacation is having a strategy — and that strategy involves early mornings. Very early mornings.

Most people on vacations like to sleep in, so to get a jump on the crowds and the inevitable long queues, you need to “rope drop.” This is Disney-speak for being at the park before it opens and first in line when staff drop the rope to allow people in. Of course, as a Disney geek, I am well-versed in all terms Disney aficionados use.

Ash Jurberg and his sons at the front of the line before the park opens.

Ash Jurberg and his sons at the front of the line before the park opens.

Courtesy of Ash Jurberg



I was worried that my sons’ sleep routine would make this impossible, but we quickly struck a deal — they would stick to my rope-drop strategy if I factored in some downtime later in the day. It was a win-win situation.

Having the right Disney strategy saves time and money

Making a deal is different from keeping one, and I was unsure if the boys would hold up their end of our bargain. We were staying at Disney’s POP Century Resort which has free transportation to the theme parks, and I wanted us to be on the very first bus to the park. As I awoke at 6 AM on the first morning to the sound of heavy snoring, I began making alternative plans. 

However, a couple of minutes later, the alarms on both of their phones went off, and my worries eased as they ignored the temptation to hit snooze and jumped out of bed. Minutes later, we were on the first bus heading to Animal Kingdom. While I had coffee to wake me up, the boys’ excitement at heading to a theme park worked as a natural caffeine equivalent. 

By being there early ahead of those enjoying sleeping in, we went on all the big “E-ticket” attractions, which is another Disney term used to define the best rides. By 1:30 p.m., the queues to these rides were huge, and it was time for me to keep up my part of the deal. We headed back to the hotel for a rest. 

As a bonus, heading back in the afternoon also allowed me to save money. Rather than buying lunch in the theme parks, we could eat in the hotel — food that I had preordered to be delivered by Amazon Fresh. Of course, this didn’t stop us from enjoying lots of tasty treats on our visit, such as Dole Whip at the parks — a classic. 

Ash Jurberg and his sons eating Dole Whip at Disney World.

Ash Jurberg and his sons eating Dole Whip at Disney World.

Courtesy Ash Jurberg



Each day, we would nap or chill by the pool to allow our batteries to recharge for a few hours. This would allow us to hit the parks again in the evening with more energy. As we reentered the parks, we would look at the tired families, dripping with sweat in the Florida humidity, who had spent most of the days in queues for the sake of sleeping an extra hour or two. For six days, we followed the same routine, with great success.

The family that Disneys together stays together 

Getting up early to go on rides is one thing, but I also wanted my sons to get into the Disney spirit. I’ve been a fan since I was a child and would watch “The Magical World of Disney” every Sunday night. I grew up in Australia, where Disney was a world away, and unfortunately my parents could never afford to take me to the US, so to taking my own children to experience the Disney magic was a real gift. Now, I was hoping that I could also pass on my love of Disney to my children. 

Ash Jurberg and his sons in the Skyliner.

Ash Jurberg and his sons in the Skyliner.

Courtesy Ash Jurberg



I was excited when, on the first day, Thomas suggested we get matching Disney T-shirts to wear as our official uniform when visiting the parks. We spent a few hours visiting stores, searching for the perfect outfits, and ended up purchasing several T-shirts and an abundance of merchandise. While I wouldn’t wear these outside the boundaries of Orlando, I loved Thomas’ suggestion and was swept up in the father-son bonding session and Walt Disney magic. 

This is the essence of what I wanted to achieve. Quality time with my kids, away from phones and out of bed, enjoying each other’s company. 

I’m now a proud Disney Dad, and my boys and I have a new tradition

I have to admit, even with all my excitement, I had been apprehensive about this vacation. I worried about whether the boys would enjoy hanging out with me, or whether they’d be bored — even despite their enthusiastic agreement to keep our reservation.

I wanted to be the Cool Dad and fretted over the possibility that instead, I would be the Embarrassing Dad or the Dorky Dad. But I quickly realized that I needn’t have worried. We had the most magical vacation, and I found I had a new title, one that I’m very proud of: the Disney Dad. 

And I’m glad to see I’ve passed the Disney gene on — Charlie and Thomas are already planning our next trip. 



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