Where I Unpack The Experience, Not Just the Itinerary
Issue 7 – August 1, 2026
Welcome to One Checked Bag.
The blog tells you where I went.
The newsletter tells you what I learned once I got there.
Sometimes that’s about travel. Sometimes it’s about life. Usually it’s a little of both.
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The Dog Days of Summer
Here we are, quite literally, in the dog days of summer. In case you were wondering, it’s not just a phrase. It actually refers to the period from July 3rd to August 11th.
Hot, humid, lazy days. I find myself trying desperately to escape the heat.
With the start of school being just around the corner, families are trying to get one last trip in before the kids go back to the classrooms.
As I think about those days, I remember the crowded beach in Hilton Head. The kids couldn’t seem to avoid the jellyfish stings. My sunburned skin, tender to the touch, would peel for weeks afterwards. And our tempers would flare under the brutal heat. These conditions were a recipe for tears, from the kids and parents. Yet, I miss those days. I think I appreciate them more today than I did back then.
In recent years we have taken the kids and grandkids to Disney World in Orlando. The park known as the “Happiest Place on Earth” can be challenging in the oppressive Florida humidity—especially in August.
Kids are experiencing sensory overload from the rides, characters, and the sweet treats. Parents are questioning the cost of the park and why they would put themselves through this for their seemingly ungrateful children. Now as a grandfather, I get to be a spectator to the calamity.
At the moment, they can seem wonderfully ungrateful. But they will forever cherish that time with you—it just may be years later. And by that time, all the frustration will be forgotten.
Looking through my photographs from our two recent trips to Disney, it seemed that everyone’s cheeks were bright red from the heat and our hair was drenched in sweat (or maybe it was from a late-afternoon thunderstorm). Smiles appeared hard to come by with each request to pose (I laughed out loud at the expressions that screamed, “Not another picture”!).
But the pictures that really moved me were the ones of my granddaughters as they met the princesses. They were mesmerized!
It was those moments that made every penny spent, every tear shed, and every tantrum worth it.
Sometimes the best family vacations aren’t the easiest ones. However, they’re the ones we appreciate more with time.
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The Road Less Traveled
Over the years, I have visited 38 of the 50 states. My goal is to make it to all 50 states.
As I looked more closely at the states I haven’t visited, I realized that many are home to national parks I’ve never experienced.
All this time, my focus had been on visiting all of the states. Essentially, I wanted to be able to say I had been there.
But now, I have a reason why I want to visit each of these states—to see and enjoy our national parks.
This could be the ultimate road trip!
My initial thought was to take three, maybe four, months and visit each of the 48 contiguous states. I could buy a Mercedes-Benz Sprinter camper van and hit the road with my wife and dogs. Starlink internet service would allow us to work from anywhere. Along the way, I would chronicle our journey with blog posts and photographs.
There is so much I have yet to see and experience in the United States and this seems like the perfect plan to see our country.
The more I thought about it, the trip appeared to have the makings of a dream adventure, or possibly one we’d regret even before driving down Route 66.
I mapped out what seemed to be the most efficient route for this trip. The route made sure we saw the foliage in New England while avoiding the desert of Arizona in the summer. The national parks were included, as were the other locations that were must-see destinations, like the Great Lakes.
After that exercise, my excitement about this adventure cooled down considerably.
The route, covering roughly 30,000 miles, would take a total of 190 days—and that assumed everything went as planned!
The question was no longer whether I could be away from home for more than six months. It was whether I even wanted to be on the road that long.
There is a lot of planning and logistics involved to make this a reality.
Yet, there is something so appealing to me about this journey.
Am I thinking like the 21 year old version of me? That guy could have lived in a camper van for 6 months. But this 60-something year old?
Call me crazy—I think this old man still has it in him!
Sometimes the journey we dream about tells us as much about ourselves as the places we’d like to visit.
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What’s in My Carry-On?
After my Miniature Schnauzer passed away, my Yorkshire Terrier would escape the house trying to find her. It was heartbreaking losing her, but even more so seeing how Coco would search for his best friend.
Fearing that I would lose Coco, too, I bought an Apple AirTag and attached it to his collar.
One afternoon, Coco escaped from our backyard deck while I was grilling. He quickly left our yard and headed towards the woods behind our neighborhood. As I yelled his name, a bunch of the neighborhood kids joined me looking for him.
Armed with my iPhone, I was able to see the direction he was headed. Here I was, yelling Coco’s name while relaying to the kids his movement through the neighborhood. I can still remember the relief when one of the neighborhood boys came from behind a house carrying Coco.
And just like Coco, the thought of losing my luggage, and in particular, my carry-on with my laptop and camera, is unsettling. So now, I would never consider traveling without an AirTag hidden in my bag.
It’s such a small price to pay for the protection and peace of mind.
After all, peace of mind is one of the best things you can pack.
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One Thing I’d Do Differently (If I Can Bring Myself to Let Go)
I fear I am making this newsletter into a dog-themed issue. But the thing I would do differently relates to dog boarding while I travel.
Any traveler who is a dog owner can attest, boarding expenses are almost as expensive as the trip itself!
With three dogs, the price quickly escalates into four-figures. Recently, our dog boarding while we were in Morocco was almost $1,500. Our accommodations in the riads were less expensive.
Maybe not having dogs should be the thing I’d do differently. But that won’t happen. I can’t part with my loyal companions.
So rather than boarding the dogs while we are away, I would like to try a house-sitter.
The dogs would not go through the stress of being in a kennel. The nightly cost is considerably less than boarding. And the only downside would be that a stranger is in our house while we are away (what could go wrong, right?).
There are reputable house / pet sitter services out there. Some are affiliated with a company, while others freelance. My fear is we’d become one of those horror stories you hear about.
The thought of damage to the house, theft—gasp—or my dogs being left unattended feels more vivid than the possibility of returning to happy, well-cared-for pets and a clean house. I don’t usually jump immediately to the worst-case scenario, so why am I doing it here?
So the question remains, can I get over my concern if it means we can save some money while making the time away less stressful on my pups?
Letting go is sometimes harder than leaving home.
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Zipping it up…
If you haven’t visited the blog, the address is www.onecheckedbag.com.
I recently published a Q&A post about our adventures in Marrakech and the Sahara Desert, as well as a post about how food becomes part of my travel experience. And there is so much more coming soon, especially with our 7-night cruise to Roatan, Cozumel, and Costa Maya right around the corner! Three generations of our family cruising on the MSC Seascape should provide some good stories, lasting memories, and lessons learned from multigenerational travel!
You can find me on my blog, Instagram, and Pinterest.
I’ll see you back here on August 15.
If you enjoyed this, forward it to someone you’d travel with.
—Stephen
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