The One Checked Bag Newsletter - Issue 4

Where I Unpack The Experience, Not Just the Itinerary

Issue 4 - June 15, 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.

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.

Why I Prioritize Travel…

I came to travel later in life.

I had always dreamed of traveling. But it was always, “Someday I’ll…”. Someday I’ll go there. Someday I’ll do that.

But that “someday” was never happening.

I could make every excuse in the book.

I’m too busy at work. I have an exam in grad school. It’s too expensive. I don’t have enough vacation time. Who will watch the dogs?

Our family vacations were to see my parents in Hilton Head. Don’t get me wrong, it was a very nice destination, but it was all I thought I could afford. Plus, I could work if I had to and had built-in babysitters (thanks Mom and Dad).

Coligny Beach and The Salty Dog were our annual stops.

Fast forward several years and my (now) wife wanted to take an all-inclusive vacation to Mexico. I didn’t even have a passport.

Our original trip was postponed because of work. History seemed to be repeating itself.

Then we finally made it.

Coming out of the airport in Cancun, I looked up at the swaying palm trees. I could hear the whistling of the wind through the palm trees’ fronds. I felt the heat on my face, bringing comfort and relief, rather than looking to escape to an air-conditioned room.

This was all new to me.

Mexico became an annual destination for us for several years. It was about escaping our daily lives. And it worked.

I would return home refreshed and renewed, ready to tackle work again with vigor and determination.

Then we discovered cruising and found we loved the variety, on and off the ship, that cruises offered.

We snorkeled with sea turtles in St. Thomas, sailed on a catamaran while jets took off over our heads in Sint Maarten, and explored ancient forts on Caribbean islands.

But for me, everything really changed during our first trip to Europe.

Paris, Florence, and Rome opened my eyes to personal growth and enrichment through travel.

I would try to speak French and Italian with our (very) patient waiters and bartenders. Museums and churches made me feel something so fulfilling. The architecture was unlike anything I had ever seen.

We stayed in a hotel built in the early 1500’s in Florence overlooking the art school and the hills from where Michelangelo once lived. I couldn’t help but be moved by the history that took place where I was. By the way, I highly recommend Hotel Loggiato dei Serviti, as does Rick Steves.

This trip changed my view of the world and travel forever—and then COVID struck.

It took a while for us to return to normalcy. But as soon as it was safe to travel, I was committed to continue to build upon my travel experiences.

I am a better person because of travel. I have grown as a person.

My views of the world, history, religion, and humanity have changed.

Why? Because I now think and speak with a frame of reference that was missing before I explored new destinations.

I don’t pretend to know or understand everything, but I now view the world with curiosity.

And now that I’m 60, I find myself thinking about legacy. Oh, the L-word! I must be getting old!

But what I have discovered through travel is something I want my children and grandchildren to discover much earlier in life.

That is the legacy I would be proud to leave behind.

So when my granddaughter asked me a few days ago to take her on an adventure, it made me very happy. Maybe my hope for them is being realized.

The Road Less Traveled

Are you an adventurous eater?

Compared to my family, and most friends, I am probably one of the more adventurous people I know when it comes to the foods that I will try.

I can’t think of much that’s truly off limits for me.

I was in Lafayette, Louisiana for business and stopped into a local restaurant. I asked the waiter what was in a Boudin Ball. His reply was simple. “If you need to know you probably won’t want it.”

As you can probably guess, I placed an order of Boudin Balls and loved every bite.

I actually seek out opportunities to test my culinary limits. YouTube has helped me identify some of the local specialties that I add to my “must try” list when visiting.

In Florence, Italy, I tried Lampredotto. It's an amazing sandwich consisting of slow-cooked tripe (the lining of a cow’s stomach) on a roll soaked in its broth and topped with a hot sauce. Afterwards, it took a few days before my wife even considered giving me a kiss.

In Marrakech, Morocco, I ventured into Jemaa el Fnaa for Snail Soup. It was so good, I kept going back for more!

And the beef tongue, or Lengua, in Barcelona could not have been more tender.

But the dish that had my stepdaughter running out of the restaurant as I took the first bite was Chapulines, or Grasshopper Tacos.

I made a list of local dishes I’ve tried in my travels that pushed me outside my comfort zone. Some may seem tame, like frog legs (and yes, they do taste like chicken) while others may push the limits of many, like bone marrow.

But food, in my opinion, is part of the beauty of travel and helps connect me to the culture of the country and its people.

Do you agree?

Sometimes the road less traveled starts with the thing on the plate you almost didn’t order.

What’s in My Carry-On?

The thought of being bogged down traveling with too many “things” actually stresses me out.

I’m somewhat of a minimalist traveler, opting for the essentials rather than bringing things “just in case” I need them.

So you would think that my Apple AirPods Pro would be the perfect headphones for me…and they are, everywhere except on an airplane. Especially if there is a nearby crying child, or an obnoxious adult acting like a child.

I purchased the Bose QuietComfort Headphones at Costco for under $200 and they have quickly become “essential” for me, for work and for travel.

My office is in a co-working space. Often, people will take their phone calls in the open area, rather than one of the designated phone booths or offices. I throw on the headphones and I am in my own little world.

On a plane, I hear nothing over the audiobook or podcast that I am listening to. This is amazing. But if my eyes are closed, I am prone to miss the drink or food service.

Had you asked me a year ago if I would ever need headphones that don’t fit neatly in my pocket, I would have said no way.

Now, they never leave my bag.

One Thing I’d Do Differently

I wouldn’t call myself a stingy person. I’m not even sure I would refer to myself as frugal. Wait…is stingy worse than frugal or is it vice versa?

Anyways, I am cost-conscious.

To that end, I find that when it comes to buying luggage, I tend to go for the least expensive alternatives.

Has it worked for me?

Let’s see.

A wheel was ripped off of my suitcase in Cancun. I was quite the sight dragging that suitcase from baggage claim to our shuttle, but at least that was on a flat surface. Once at the resort, however, the sidewalk to the door was cobblestone. What a fiasco!

In Amsterdam, the retractable handle broke and became dislodged. The sharp, exposed metal rod would have made a good weapon if needed.

And my Apple MacBook Pro has a nice big dent from when my 40-liter backpack strap’s buckle failed when hanging from a bathroom stall door at BWI.

So, no. It hasn’t worked well for me at all.

With two major trips scheduled in the next four months, I am looking into investing in high-quality luggage with a strong warranty.

Travel will be a mainstay in my life for as long as I am able. Why frustrate myself with inexpensive and unreliable luggage?

Good travel gear isn't about owning more things. It's about removing friction so you can focus on the experience.

Zipping it up…

If you haven’t visited the blog, the address is www.onecheckedbag.com.

My most recent blog entries discuss my thoughts on cruises and a review of the MSC World America, a beautiful new mega-ship.

With summer break from school just days away, I’m looking forward to a cruise we booked with my wife, step-kids, daughter, son-in-law, and grandchildren.

I hope to report back to you with our keys to a successful multi-generational vacation and some lessons we learned from what may or may not have gone as we hoped or planned.

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

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

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

—Stephen