The One Checked Bag Newsletter — Issue 9

Where I Unpack the Experience, Not Just the Itinerary

Issue 9 — September 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.

Hiring a Local Tour Guide

If you’ve ever been on a cruise, you’ve probably been approached at the ports by people offering to drive you somewhere, take you on an excursion, or show you around.

I had always considered this kind of sketchy.

With a simple “no,” we would walk past and start exploring the area on our own. Sometimes we had a destination in mind. Other times, we wandered around aimlessly and hoped we would stumble upon something interesting.

And sometimes we did.

The problem was that we often had no idea what we were actually looking at or why it mattered.

Clearly, we weren’t getting the most out of visiting that particular place.

On our recent multigenerational cruise, one of our stops was Roatán, Honduras.

The day before, we had spent a fair amount of money on a beach day in Mahahual, Mexico, so we decided to take it easy in Roatán.

We disembarked and started walking without much of a plan.

As you leave the cruise port in Roatán, there are about a dozen vendor booths with somewhat pushy salespeople offering excursions.

I shouldn’t call them pushy. They’re doing their jobs.

And my job at that moment was to say “no” to whatever they were selling.

But then, as we exited the excursion area, I let my guard down.

A gentleman in a bright orange shirt asked if we would like a private driver for the day.

I hesitated.

But it was extremely hot that morning, and the thought of eight of us wandering around in that heat felt like the makings of miserable grandkids and flaring tempers.

He offered us a private driver for the day in a nicely air-conditioned Mercedes Sprinter van. And to sweeten the deal, he threw in admission to a sloth and monkey sanctuary for all eight of us.

For the first time, I said yes.

What we experienced that day was very different from what I thought I was saying yes to.

The sloth and monkey sanctuary was great. Dipping my toes in the ocean at West End with my granddaughters was a nice escape from the sweltering heat. And the little shops and restaurants across from the beach were fun to poke our heads into.

But what really made Roatán memorable was our driver.

As he drove us around the island, he told us about the places we were passing. He showed us areas where many of the local workers live and areas where expats from the United States and Canada are building homes.

He explained the school system and the schedules students keep throughout the year. We learned about the economy, the churches, and the island’s expanding infrastructure.

He drove us to one of the highest points on the island and explained what we were looking at below.

But the real treat was driving through the area where he grew up and then past his current home, right on the ocean.

He beamed with pride as he talked about his island.

When we returned to the cruise port, we said goodbye to our new friend.

More than an air-conditioned ride, he gave us something we never would have found wandering around on our own: a glimpse into what life on Roatán is actually like.

I’m still not suggesting you say yes to every person holding an excursion sign outside a cruise terminal.

But I may be a little slower to automatically say no.

Sometimes the best way to understand a place isn’t to wander around it.

It’s to spend a few hours with someone who calls it home.

The Road Less Traveled

As we prepare for our trip to Asia next month, time seems to be flying — and I am definitely behind on planning the details.

To say I’m starting to get nervous would be an understatement.

We haven’t even decided whether we’re staying in Taiwan for the entire trip or also visiting another country, such as South Korea or Japan.

It’s hard to plan when I don’t know where we’ll be or for how long.

So, with a seemingly endless number of possibilities, I’ve been leaning hard on AI to help me plan.

And to be honest, it almost feels like cheating.

I feed information into an AI platform — dates, budget, travel style, interests, and so on — and it gives me itineraries, tips for navigating the country, and recommendations for lodging.

It even told me where to go for the perfect Instagram-worthy picture.

What normally takes me hours of research, analysis, and scheduling can now be done in minutes.

Is it perfect?

No.

But part of that is probably user error.

How would it know that I don’t consider a hotel charging $700 per night “budget-friendly” if I don’t give it the proper parameters?

AI has made my travel planning much more efficient, and I can absolutely see it replacing a lot of the grunt work that used to take hours.

But our day in Roatán was also a good reminder that there are still some things technology can’t give you.

AI may help me figure out where to go, but it can’t (yet) replace the personal touch and experience that makes the destination memorable.

What’s in My Carry-On?

As I’ve transitioned from being a casual traveler to someone who would actually like to make a living traveling, I spend a lot of time watching YouTube videos from other travel content creators.

Where to eat, what to see, and Wolter’s World’s lists of Do’s and Don’ts keep me entertained and informed.

Some of my favorite videos are the ones where creators share their favorite travel accessories.

These range from the incredibly useful to the absolutely absurd.

Some of these inventions seem like something Ron Popeil would have sold on a late-night TV infomercial. You know — the guy behind the Showtime Rotisserie and the catchphrase, “Set it, and forget it!”

I understand how people lose track of time watching TikTok videos because, somehow, I recently watched two straight hours of travel-accessory videos.

Then I spent another hour looking at some of those accessories on Amazon.

Other than a few necessities — my noise-canceling headphones and a backup charger for my phone come to mind — I prefer to travel extremely light.

Those aluminum water bottles seem clunky and add weight.

Neck pillows are great in theory, but they take up a ton of space in your bag. And wearing one while leaving the airport — especially in Cancún — is a pretty big faux pas.

All the various travel gadgets usually just mean more weight and more things I have to keep track of.

Maybe someday I’ll feel differently.

Until then, I’ll keep watching these videos (a big shout-out to the YouTube channel Away Together w/ Nik and Allie) and try to resist making that Amazon purchase at 1:00 a.m.

One Thing I’d Do Differently

Or maybe this section would be better titled:

One Thing I Wish I’d Done a Long Time Ago.

The funny thing is, I had the ability to do this for years before I finally did it.

Accessing airport lounges has been a game changer for me.

I’m sure you’ve seen them in airport terminals: American Express Centurion Lounges, Delta Sky Clubs, Capital One Lounges, and others.

Access is restricted, usually to certain cardholders or travelers with airline status.

And yes, it comes at a cost.

But for me, it has been worth it.

My American Express Delta Reserve Card has a $650 annual fee and gives me access to the Delta Sky Club 15 times per year.

Ignoring all the card’s other benefits, that works out to about $43.33 per lounge visit.

On the surface, that sounds expensive.

But the “free” food and drinks help offset some of that cost.

And by “free,” of course, I mean included in that $650 annual fee.

Most lounges offer alcoholic and non-alcoholic beverages, buffet-style meals, snacks, Wi-Fi, and comfortable seating.

But the real value for me is the quiet place to work or relax.

Before I started using lounges, I would usually go to an airport restaurant or bar and try to work in a very limited space while spending more than $40 on a couple of drinks and questionable food.

Or I’d grab a cup of coffee and sit at the gate with my laptop on my…well, lap.

Neither option is particularly conducive to productivity or relaxation.

Now I actually make a point of arriving at the airport early.

I can grab a meal, have a beer, catch up on work, or simply relax after dealing with security lines and the general chaos of the airport.

What I once viewed as a luxury is now something I consider a travel necessity.

Zipping It Up…

If you haven’t visited the blog lately, you can find it at www.onecheckedbag.com.

I’m admittedly behind on my blog posts, although I have several semi-completed drafts sitting there waiting for me.

I guess that’s the curse of a perfectionist.

New content is coming soon. I promise.

Taiwan is right around the corner, and I think we’re going to add Seoul, South Korea, to the trip.

But even that is still subject to change.

I’ll also be sharing more from our multigenerational cruise on the MSC Seascape. My 5- and 7-year-old granddaughters gave me some great feedback while I spent time with them last week — including observations about the cruise I never would have noticed on my own.

You can also find me on Instagram and Pinterest.

I’ll see you back here on September 15.

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

—Stephen