The One Checked Bag Newsletter – Issue 8

Where I Unpack The Experience, Not Just the Itinerary

Issue 8 – August 19, 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.

Multi-Generational Travel

I’m five days late with my newsletter. My apologies (kind of). Though disappointed it wasn’t published Saturday, I have an excuse I can live with.

I just returned from a 7-night cruise with my wife, stepkids, daughter, son-in-law, and granddaughters. Though I had every intention of working while on the cruise, I was only able to muster the motivation one day to sit down and write. That ended once I received a text from my daughter telling me that my granddaughters were asking for me.

My readers can wait, but my granddaughters can’t.

Seven nights on a cruise ship, plus a night in Galveston beforehand, can be a long time together. This is especially true with the ages ranging from 5 to 61. But it honestly could not have been better.

No tears and only smiles.

It can be challenging finding activities on and off the ship that everyone could enjoy. Somehow we managed to do so.

What kids may enjoy eating can differ from that of young to not-so-young adults. Yet, somehow we were able to find restaurants and menu items to accommodate us all. And the kids even tried escargot, octopus, and clams on the halfshell!

Watching my granddaughters belting out the songs at the evening shows and dancing at the White Party late into the night brought a smile to the faces of us all…and even some of the fellow passengers.

I attribute the successful navigation of all these challenges to careful planning, cooperation and compromise from all, and patience.

There will be a blog post about the cruise ship and ports on www.onecheckedbag.com. I am looking forward to sharing our experience of the MSC Seascape and the ports at Costa Maya, Roatan, and Cozumel.

While it is fresh in my memory, I am working on content to share about the keys to a successful multi-generational vacation.

There are few things that I have enjoyed more than bringing the family together outside of the normal holidays (Thanksgiving, Christmas, etc.). This is our fourth annual multi-generational vacation and we’ve decided that it will become our family’s annual tradition.

If you have the chance to bring the family together like this, do it. I am sure my granddaughters won’t remember every detail of the trip, but their grandfather will never forget.

The Road Less Traveled

I am running an experiment.

Our last three trips have been over a week in duration. Thinking I needed clothes and shoes for every foreseeable occasion, I brought a large hardshell suitcase. You know the kind. The kind of suitcase that you pray doesn’t exceed the weight limit when you place it on the scale while checking in.

Upon my return from each trip, at least one-third of the clothes I brought were not worn. They were packed and unpacked at each destination. They were hung in the closet to help get the wrinkles out, only to get re-wrinkled when packed for the next leg of our journey.

Yes, I had enough clothes to provide me with options each day or night. But what was I going to do that would have required me to fret over my attire? It is highly unlikely that I’ll dine at a Michelin-Star restaurant (or one that requires a jacket and tie).

So on this cruise, I chose a smaller suitcase.

Do you know what happened?

I came home with a third of my clothes unworn. I think my underwear was the only article of clothing fully used (thank goodness I could plan that accordingly).

I am convinced that the extra articles of clothing are not options as much as they are clutter.

Not only do they take up space in my suitcase, but also in my mind as I try to pick out what I am going to wear. I think Steve Jobs was on to something with his black shirts. Why do I want to waste any mental decision-making energy while I am on vacation?

The experiment continues next month. I’ll size it down once again, this time with a (yet) smaller suitcase.

I don’t want to be weighed down, literally or figuratively, while on vacation.

A two-week trip to Asia will be the true test. Hopefully, my experiment will pay off!

What’s in My Carry-On?

At this point in my life as a traveler, you would think I would be an expert on all the perks that come with my credit cards, loyalty programs, and the like. Not so.

In fact, I am embarrassed to say that my college-age stepson understands the perks much better than I do. On this last trip he “enlightened” me several times on the benefits I’ve been missing.

I have always paid attention to earning points or miles on my Delta and Southwest branded credit cards. In a recent post, I discussed the hotel loyalty reward programs and Expedia. Those have also been very important in my travels.

But I’ve been missing out on the less obvious perks, some with my credit cards and others with services I use, like my cell phone.

As we flew from Atlanta to Houston, I was scrolling through the Delta App when I saw that T-Mobile members could link their T-Mobile ID with their Delta SkyMiles account and receive a free premium drink (beer, wine, or cocktail).

While I watched passengers reach for their wallets, my wife and I showed our phones and received a free drink.

And this isn’t just offered on Delta. Southwest, Alaska Airlines, and Hawaiian Airlines also offer the free drink.

That’s just one example.

As I perused my T-Mobile App, I stumbled upon T-Mobile Travel. You can book your hotels, cruises, rental cars, and/or flights at discounted or competitive rates, plus potentially extra benefits.

This discovery sent me down a rabbit hole. What else have I been missing?

Well let’s see…Delta SkyMiles rewards for purchases at Starbucks and cashback when using rideshare apps, just to name a couple. They frequently change, but as I write this, both are active benefits.

The cell phones we carry everywhere with us may hold a variety of untapped benefits.

Take a break from playing Candy Crush for an hour or so and investigate what you may be missing. Often, the effort is a one-time linking of accounts or opt-ins. Other times, it may just be a slight modification of your routine.

I’ll continue to share what I find with you. I’ll never be The Points Guy, but hopefully what I do find can benefit us all!

One Thing I’d Do Differently

The night before our cruise, we stayed in Galveston, walking distance from the cruise port.

I was really looking forward to spending time with my granddaughters pre-cruise. I wanted to hear all about their flight and what they packed for the cruise. And I was really looking forward to the short walk with them from the hotel to the cruise ship the next morning.

Two rooms were booked for us at the hotel, one under my name and the other under my daughter’s name.

We arrived at the hotel a few hours before they were expected to be there. We checked in, went to the room, and then started to explore the waterfront restaurants and The Strand (where the shops and restaurants were located).

During a quick bite and beer at a taco place, I received an email from the hotel about my daughter’s reservation. I quickly walked to the hotel and learned that they bumped her from that hotel to a sister hotel about three miles away.

The reason they provided was unacceptable, in my opinion, but when it came down to it, the situation could have been avoided.

I could have told the front desk clerk that we were with another party, but they were delayed. I didn’t think I needed to, partly because I prepaid for the rooms, but mostly because I have never had a hotel choose to bump a reservation in favor of another guest.

After another beer (and a really deep breath), I realized I could have reduced the chance of this happening by alerting the front desk that they were on their way, but I didn’t.

In hindsight, it’s probably better that they were able to arrive at the cruise terminal in an air-conditioned vehicle. That short walk in the Galveston heat and humidity was brutal!

Zipping it up…

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

I recently published a post about cruising in Alaska. After two cruises to Alaska, I have some opinions on the importance of the cruise ships and itineraries when deciding on your Alaska adventure.

With our trip to Taiwan quickly approaching, I am excited about creating content to share with you about our planning for and expectations of the trip. This will be my first visit to Asia and my excitement level is off the charts!

And because one trip to Asia isn’t enough, we just booked a trip to Saudi Arabia!

And as promised before, I will be sharing our multigenerational travel experience on the MSC Seascape, complete with tips from the lessons I’ve learned.

You can find me on my blog, Instagram, and Pinterest.

I’ll see you back here on September 1.

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

—Stephen