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Writer's pictureMyRooftopStories Team

Travels With My Dad



One of my favorite Netflix shows is British Comedian’s Jack Whitehall’s Travels With My Father series. Jovial and carefree, Jack invites his stodgy “Daddy,” Michael, to go on trips with him to different parts of the world. In this four season series, the father and son duo have explored Southeast Asia, Europe, America’s Western States, and Australia. What follows is laugh out loud comedy of their mishaps, adventures, and witty banter. By the end of the first trip, their bond was definitely stronger, and they had a lot of fun along the way.

We all have family vacation memories. In fact, these memories are the ones we remember with the most fondness from our childhood. The trip I took to Jamaica as a child with my family are some of my earliest memories. What is your most memorable family vacation?


As we are approaching Father’s Day in a couple weeks, I asked my team to share a travel memory they have of their dads. Happy Father’s Day to all the fathers in our lives! Thank you for helping us make lasting travel memories.


Stokes O'Shields with her father, James.

Trips with my dad are always fun ;)


My first trip to Nashville was with my dad. We went there to tour Vanderbilt University and see if the city would be the right fit for me. The best part of trips with dad is the soundtrack. As a musician with a vast variety of genres he listens to, it is always a fun time. That trip in particular, as we were headed to “Music City,” and the home of the Country Music Hall of Fame, we listened to a ton of country music. It included songs I had not heard since my childhood. I can’t listen to most Shania Twain and Carrie Underwood songs without hearing him sing along, loudly and off key. It was amazing.


Dad’s love to try to embarrass their kids and be goofballs, and I learned long ago if you lean into it, it’s 100 times more fun.

~Stokes O'Shields



Chelsea Craig with her Dad, Tom.

My dad Tom is quite the exceptional human, and he brings his extraordinary spirit with him wherever he goes. One moment that stands out is when we took a family trip to Arizona. My dad collects kaleidoscopes (the fancy-schmancy artistic kind) so we drove up the side of a mountain on a single lane road (which was just as nerve-wracking as it sounds) to check out one of the most well-known kaleidoscope shops in the world - Nellie Bly Kaleidoscopes. We spent hours looking through beautiful pieces of art and then, at the end of the day, we got to go into the exclusive collector’s room. I’ve yet to be as awe-struck as I was in that room. It was an amazing memory, and I love we could spend so much time taking in dad’s passion for his collection. It felt really special, and it is one of the standout memories of my lifetime.

~Chelsea Craig



Michael Duncan with his father, Jonathan.

The most recent trip I took with my father was to Asheville, North Carolina, in the summer of 2020. (The Covid Summer) It was fun to travel alone, just the two of us because that does not happen very often. We explored all around downtown, stopping into the local eateries and shops. We also went to one of the biggest houses in the United States, the Biltmore Estate. It is massive, filled with rooms, including a bowling alley in the basement. But my favorite part of the trip was exploring the Blueridge Mountains driving along the scenic Blue Ridge Parkway. My dad and I finished our trip with an amazing hike that made you feel completely immersed in nature.

~Michael Duncan


Swinging at the beach with Charlotte.

There is not one particular family vacation that stands out (and no that is not a bad thing) but, rather, a location we visited frequently as we were growing up. Figuring out where to travel with three kids, and occasionally a few dogs, must have been thought provoking for my parents... but in our opinions, they nailed it. They would take us (collectively the Sanderson kids) to St. George Island and Appalachicola, both of which are on the panhandle of Florida. To us, it was appropriate because we love quiet beaches and local culture. In hindsight, as adults, we find it incredibly special that we were given these experiences over more popular kid vacations (i.e. Disney in Orlando). We explored the beaches and enjoyed the vibe it allowed.

This short piece is difficult for us to write as our Father died last year. We visited St. George and Appalachicola during Spring Break this year. It was the first time we had visited without him. Although, maybe that last statement is not so true. We are not sure how we feel about spirits and what happens after death, but we can say we felt his presence when we were at the park in Apalachicola. There is a playground by the docks there that we visit EVERY single trip. It was also where Dad used to push us on the swings (we as a family love the swings). This time (during Spring Break), we were able to share it with his grandchild, Charlotte. She, like her family, loves to swing, and it is magical something so simple can bring us all closer together in life and death.

~Katy Matello and Martha Sanderson



Abbi Stickels with her Dad.

Although I haven’t had much time to travel with COVID-19, I’ve moved a couple times in my life now, and every time I have, my dad has never failed to show up! First into my freshman dorm, then into a sublease, and later into my first apartment. All the moving chaos is always rewarded with Ian’s pizza and a good laugh or two. I could never imagine my travels to college and around town without my dad’s help. I’ll hold on to these memories for years to come.

~Abbi Stickels



Julia Duncan (2 yrs old) with her Dad.

Julia (22 years old) with her Dad, Jonathan.

The first time I went to Disneyworld I was a toddler, and I took a picture in front of the castle with my dad. Since then we’ve been there three more times. This past Christmas we spent it at Disney and we recreated the photo, but this time I was blonder and tall enough to ride the more adventurous rides with my Dad.

~Julia Duncan



Gina Duncan with her Dad, Eddie.

When I was younger, my dad would take my brother and me to horseback riding ranches in upstate New York. I rode a horse for the first time on these trips. It was fun being led around the fenced in area. But when it was time to join the group on the trails, I remember being a little fearful. My dad encouraged me and eventually we were off riding with the others. I also learned how to fish during these vacations.


The nights at the ranch were also fun. After the family style meal, there would be entertainment. They would have a comedian, a magician, music, or dancing. I know their parent’s dance moves embarrass some kids, but not me. I think I got my love for dancing from my father; we were usually the first on the dance floor.


Our annual trips to the ranch and barbecues at the beach are my favorite memories of traveling with my dad.

~Gina Duncan



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