The One Checked Bag Newsletter - Issue 2 (May 15, 2026)

Welcome to One Checked Bag.

This newsletter is where I go a little deeper than the blog—less “what to see,” more what travel actually feels like, what I’d do differently, and what matters once you’re there.

I’ll be here twice a month, sharing stories, reflections, lessons learned, and a few surprises along the way.

Thanks for joining me on the journey.

Does Advance Preparation Kill the Enjoyment of Travel?

Ok, confession time.

Before I leave for any vacation, especially for international travel, I watch hours of YouTube Videos, read numerous blog posts and magazine articles, and engage ChatGPT to help me plan.

I know where I want to go, what I want to eat, and everything I feel I need to experience. I prepare itineraries galore. I map out what I believe to be the most efficient routes. I even go to the restaurant websites to read their menus and plan what I will order.

TripAdvisor, Facebook Groups, and Instagram can take me down rabbit holes.

Yes, I can become obsessed with the trip before I ever set foot on the plane.

But I am starting to learn that I am only setting myself up for disappointment. And if I am traveling with others, I am likely setting them up for disappointment or frustration as well.

How is that not the likely outcome if everyone comes with a different set of expectations and desires?

This really hit home while we were in Paris. We had the 48-hour Paris Museum Pass, which allowed us access to several museums and attractions, but only for 48 hours.

Maybe my expectations were unreasonable and unrealistic. To maximize the museum pass, we moved quickly through each museum and then raced to the next. And though we were able to visit most of the destinations on our list, it left something to be desired.

Strict adherence to an itinerary starts to feel like work.

So what can be done to alleviate this problem? Or is it just inherent when traveling to a destination for the first or second time?

I am not sure if I have the perfect solution, but I think I have a plan that may work.

Start with understanding the expectations and priorities for everyone in your party. Communication is key.

If the expectations and priorities don’t mesh, either compromise or part ways for a period of time and then reconvene. And if you compromise, live with that decision and don’t complain about it later.

Build a loosely structured itinerary that allows for flexibility and additional time at a location, if desired. Adhering to a rigid schedule has worked against my travel partners and me in the past. Don’t allow an extra 30 minutes at lunch to throw a wrench into your plans.

And remember, if you find you are stressing out over keeping to a schedule, you are defeating the purpose of getting away. Take a deep breath, look around at where you are and what you are experiencing, and just enjoy the moment!

I will still do my research before each trip. I think that is embedded in my DNA. But as it relates to my travel plans for this fall (I’ll share these at a later time, but I am incredibly excited to share them with you), I plan to do exactly as I outlined above with my wife.

I wish I had THE solution. It is still a process of trial and error for me. But I learn more with each trip.

If you have any tips or thoughts, please share them with me. I would love to update our community with what works for you.

The Road Less Traveled

While we were in Paris, there was a moment that really made an impression on me. Not a grandiose event. Not something of historical significance. It was remarkable to me for the simple pleasure it provided.

It happened during a walk through Luxembourg Gardens.

As we approached the pond, I told my wife that I was going to walk around to take some photographs. I wasn’t particularly inspired by what I was seeing through the lens, but I kept walking around looking for “that shot”.

A young couple approached me and asked if I would take a picture of them. She handed me her camera, and they posed by the stone terrace.

The birds were singing. The sun peeked through the clouds, briefly shining on them. With his arms around her, she looked up at him with undeniable affection. Snap, snap, snap…I took several pictures of them in that moment.

I got “that shot”! It just wasn’t on my camera.

What’s in My Carry-On?

I am very much a minimalist. When I vacation, I am looking for experiences, not things.

In fact, except for a couple of watches, I can't think if anything that has been purchased on a trip that I use or is displayed in our house. Ok, maybe I am lying just a little bit.

But my point is that when I travel, I want to see, hear, smell, taste, and feel my destination. I don’t want to bring back “stuff” to an already cluttered home.

To that end, I capture my experiences primarily in pictures.

I read somewhere that the best camera you can have is the one you have with you. I don’t think truer words could be said about cameras.

In today’s world, everyone has an incredibly powerful camera on their phones. And what could be more convenient than something that is always on your person?

Yes, I take a lot of pictures with my iPhone. Some are really good.

But it is my trusty, 10-year-old Panasonic Lumix GX85 camera that ignites something in me. My creativity is elevated to another level as I frame the picture in the viewfinder. I am more aware of my surroundings. Textures and depth of a scene are felt as I compose the shot. The click of the shutter signifies my readiness to capture the moment. I have a totally different experience and perspective when I use my camera, one that is much more fulfilling.

So, if you are seated next to me on the plane, I promise that at some point during the flight, I will pull out my camera from my bag, clean the lens, check the settings, and place it back in my bag for easy access.

One Thing I’d Do Differently

Thinking back on our trip to Paris, staying in the Pigalle area was not ideal. I understand why I decided on that area at the time. But in hindsight, it didn’t feel like the version of Paris we hoped to experience.

After walking much of Paris, I like the central location and vibe of the 6th arrondissement. Proximity to all the “must-see” attractions, cafes, and the tranquility of Luxembourg Gardens.

Zipping it up…

I am really enjoying reliving some of my past travels as I post on my blog. By the way, if you haven’t visited the blog, you can find it at www.onecheckedbag.com.

As I think about it, I am thankful that I took great notes from each journey. Reading about what I was thinking and feeling in the moment is amplified with the thousands of photographs I took along the way.

It’s almost like I knew I would be sharing the stories in the future.

I invite you to find me on my blog, Instagram, and Pinterest.

I’ll see you back here on the 1st of June.

If you enjoyed this, forward it to someone you’d travel with.

—Stephen

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