Single-Parent Vacations: Michael & James’ Story

Traveling has always been a passion of mine. I love new experiences and the excitement of submerging myself into the unknown.

Whether it’s a backpacking trip through Europe or a lazy beach vacation with a loved one, I’m here for it. And while I enjoy trying new foods and sightseeing, the main reason I love it is because of the lasting memories.

It’s fair to say my travel preferences have evolved over the years. Fifteen years ago, I was an ambitious traveler, but as a single father to a 5-year-old boy, well … I now prioritize convenience over adventure.

After all, single-parent vacations with a 5-year-old are an adventure of their own.

Let’s face it … parenting is tough. As rewarding as it can feel at times, it is without a doubt the hardest title I will ever hold in my life.

I recall the days when I was a carefree, single guy in my early twenties. What did I worry about back then?

If you’re a single parent and need some insight — and inspiration — on what it’s like to vacation with your kid(s), this is my story of love, loss, adjusting to a new life and figuring out new ways to make travel memories with my son.

Our Family’s Story

Life is a rollercoaster. Well, at least for us it’s been. After losing my wife and partner of 16 years to breast cancer in 2019, I was back where I started … single, anxious and undoubtedly lost.

Except this time around, I wasn’t alone. Two years before my wife Laura had passed, life gifted us with a beautiful boy, James.



We experienced all the typical struggles commonly associated with early parenting.

In between the doctor’s visits, new parenting classes, and playdates with other kids and their parental units, we found a few hours here and there to rest.

Life was crazy, no doubt, but it was fun because we did it together. Laura was the captain of our family’s vessel and always kept us on task and on track.

And yet, all of that changed when she passed 3 years ago. And for the first time in a long time … I was lost.

Almost as if I was transported back into that 20-year-old body, except this time, I had a few more miles and pounds under my belt.

I decided early on that this tragedy would not define us nor dictate our future. It had, after all, taken too much already.

I spent months in deep reflection, wondering how life would have been different had Laura not been taken from us so suddenly. But that approach, as we all know, only leads to one place … back to where you started.

So, I changed my approach. Instead, I sought to answer one question and one question only, “If Laura were still here, what would she do?”

For one, she wouldn’t want me to waste my life away on the couch, detached from the outside world with all this existential angst. Nor would she want me to waste any more time reworking hypotheticals and all of life’s “what ifs.”

Life is for the living and the time had come to act. So, with Laura by our side, James and I began to take the first few steps into our brand-new life.

Adjusting to Our New Life

I always knew that Laura did a lot for our family, but my God, I never truly understood it until she was gone. I’m not sure how certain tasks get delegated in a household or why, but Laura did so much more than me.

She was our family’s human resources, accounts payable, procurement and warehouse manager all wrapped into one. Makes me wonder what I was doing this whole time.

It was clear I was in over my head and had to adopt some new habits quickly. Fight or flight as they say.

Before I knew it, James was going to school and outgrowing all his clothes. Time was passing us by.

My parents never failed to remind me to appreciate the moment and how important it is to create memories with James because “They don’t stay that way forever.”

Making Vacation Plans … and Canceling Those Vacation Plans

We had planned on taking a few vacations in 2020, however, those plans were quickly derailed by the COVID-19 pandemic.

With global and domestic travel at a standstill, I promised myself and James that once we were able to travel, we would not only go on vacation but it would, in fact, be one that we’d never forget.

Sadly, one year later, we found ourselves right where we started. COVID-19 was still very much part of our daily lives and was showing no signs of letting up.

Oddly, in January of the same year, I received a call from ABC’s The Bachelorette asking me whether I would like to join their cast for the upcoming season.

After weeks of deliberation, I decided to take the risk and accepted their offer … but that is a story best told on another day.

The point is, it delayed our trip once again, and by November of 2021, James had grown tired of asking me where and when our big trip was going to be.

Then suddenly, in a blink of an eye, an opportunity presented itself and I was determined not to let it pass us by.

Planning My First Big Single-Parent Vacation with James

In full transparency, I was never fond of Walt Disney World_® Theme Parks. As a child, I remember how much my dad didn’t like going, so it was hard for me not to feel the same about it.

However, Laura loved Disney, as did her parents. And I was determined to give it another shot and let James experience what has become, for one reason or another, an American birthright.

^{Disney’s Magic Kingdom_® Theme Park at Walt Disney World_® Theme Parks}

James and I had been on a few short trips before, but this was our first major vacation in two years.

I booked flights to Orlando for my family and decided last-minute to bring my in-laws. They knew the terrain and could provide some support in the off — who am I kidding, the MORE THAN LIKELY — chance that I experience a breakdown.

It proved to be a wise move later.

After the flights were locked in, I began looking for a place to stay. I needed an Orlando resort that was within short proximity to the parks, but far enough removed so that it wasn’t too close for my comfort (remember, I wasn’t a huge fan at first).

In addition, I needed a place that had everything. A golf course, pools, mini golf, onsite dining, tennis courts, watersports and large enough rooms to not only accommodate four people but also offer separation and personal privacy when needed.

^{The Putt-Putt® golf course in the West Village at Orange Lake Resort}

After creating my long list of demands, I began to think that I was going to have to make some concessions.

I spent many nights scrolling through countless Orlando resorts and hotels throughout the Disney area, and I began to grow desperate and weary.

And right before all hope was lost, like a Phoenix rising from the ashes, I stumbled upon Orange Lake Resort.

Our (Long-Overdue) Vacation at Orange Lake Resort

Orange Lake Resort literally had everything. Was this too good to be true? Maybe … but on that day, this frantic father had a promise to keep, nothing to lose, and an itchy index finger ready to press that “book” button.

James, baby, pack your bags … we’re going to Disney World!



Upon arriving at the resort, I could feel my worries begin to settle. It was as advertised. The property was not only stunning but massive.

After surveying the activity in the parking lot, it was easy to see that Orange Lake Resort was a popular choice among other like-minded, savvy travelers. And yet, it felt private, quiet and our own.

If I remember correctly, it had miles of paved road just within the resort property. Spread along these roads were 4 golf courses, 4 pool areas, 7 restaurants, 3 arcades, mini golf courses, an impressive lazy river and even more activities right on the property.

^{Relaxing at the River Island pools and getting our game on at the arcade in the North Village}

We received transportation from the check-in counter to our 3-bedroom villa in the North Village. (I mean, James waited long enough … might as well go for it, right?)

We unlocked the door and walked in. Holy smokes! This place was huge. Each bedroom was large and had its own bathroom.

On top of that, we had a beautiful kitchen equipped with all the amenities, and our view overlooked the green of the pristine par-3 golf course.

Our tribe was impressed. I was happy, and it didn’t take us long to unpack and begin exploring the resort’s tightly manicured grounds.

I couldn’t help but take it all in and enjoy one of those priceless and ever-so-rare “proud dad moments.”

^{James even found some “magic” in our room once we arrived.}

A Vacation That Meant So Much to All of Us

We spent 5 beautiful days enjoying the grounds. The resort’s relaxing atmosphere proved to be an ideal retreat from the chaos of our daily life.

I ended up giving Disney World a second chance … but this time, I got to experience it through the eyes of James … and let me tell you … it was indeed magical.

Above all, I witnessed my in-laws smile in a way I haven’t seen in years. It felt as if they were reliving trips from a previous life, youthfully walking down the same vibrant roads they once had with Laura.

For them, their treasured memories were momentarily brought back to life — no longer dulled by the weight of sadness, nor buried within the bedrock of grief.

Instead, they were resurrected as they shared stories with James and me, many of which I had never heard.



I felt her presence that week. I think we all did.

Life is often referred to as a rollercoaster … and after these past few years, I couldn’t agree more. My 20-something self would have been frightened by this comparison, but now I couldn’t be more ready for it.

I now know that nothing can break us as long as we’re together. So, jump in and buckle your seat belt cuz it’s gonna be a wild ride!


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