The One Checked Bag Newsletter – Issue 5

Issue 5 – July 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.

This week, I’ve been thinking about travel margin: making room for dreams, room for discovery, room for delays, and room for things not going according to plan.

Do you love a good cliché? I do.

There are a million YouTube videos and blog posts about “bucket list destinations.”

I think it’s so common that it borders on boring.

I used to see “bucket list” in the title and would typically keep scrolling.

That’s probably unfair. As a travel blogger, I know how much work goes into creating something useful. Still, the phrase had started to feel overused to me.

Now? I actually see value in writing down the places and experiences I want to make room for.

Why?

Twofold.

First, I believe there is power in writing something down.

Maybe the universe gets involved. Maybe writing it down simply changes what we notice, what we say yes to, and what we make room for.

Either way, my trips to New Zealand and Alaska are all the evidence I need.

I had jotted both destinations in my journal as three-year travel goals. I put the journal in my drawer, forgot about it, and found it three years later while cleaning.

Somehow, without giving it any intentional thought, both were realized within three years of writing those travel goals.

Today, I’m much more intentional about making lists of the things and places I want to experience.

Secondly, I think there is power in forward-looking aspiration.

We need something to look forward to. We need to dream. We need to believe there is something beyond our day-to-day life.

A bucket list, at its best, is not a checklist. It is a little space we carve out for possibility.

I guess you can say I am now a big fan of a good bucket list.

What have I recently added to my bucket list?

In no particular order, I’ve added:

1. A cruise to Antarctica.
2. Backpacking in Peru to see Machu Picchu.
3. Krakow, Poland
4. The Azores
5. Montenegro

Why these?

Because the content creators I once mocked for producing something cliché have inspired me.

And for that, I sincerely thank them.

The question is, what’s on your bucket list for travel?

If I were to ask 100 people to give me a list of 10 places they would like to visit, what do you think would be on the lists?

Paris? London? Maybe Greece?

How often would you expect to find Taipei, Taiwan on the list? I suspect it wouldn’t be found often.

It wouldn’t have been on mine—until recently.

But then a good deal on flights caught my eye, and Taiwan was suddenly on my radar. So when Delta had an airfare sale to Taipei for the fall of 2026, I seized the opportunity.

We are going to Taiwan in October, with Taipei as our starting point.

What do I know about Taiwan? Not nearly enough—and honestly, that’s part of the appeal!

Why Taiwan? I’m following Clark Howard’s travel-deal advice: buy the airfare deal first, then figure out why you want to go there.

What will we do there? I don’t know (but there is time to figure that out).

We have 13 days to experience Taiwan, slowly. The plan is to stay put long enough to understand more than the airport, the hotel, and the highlights.

That gives us plenty of time to experience the people, culture, food, and history without rushing from one place to another.

And though it is tempting to hit several locations in Asia while in that part of the world, I feel that rushed, check-the-box travel may not be for us anymore.

Tokyo and Seoul may have to wait.

If I learned anything from our recent trip to Europe, doing less may actually mean experiencing more.

As I write this, I am sitting on a plane traveling from Atlanta to Baltimore to visit my kids and grandkids.

My heart rate is elevated and I am trying to catch my breath.

I made it to the gate with minutes to spare.

Why?

Atlanta traffic was horrible. Then I missed the off-airport parking lot shuttle bus and had to rely on an Uber to get me to the airport. Once there, I was greeted by a long security line, even with TSA PreCheck!

None of that was in my control.

But one thing was: the time I left for the airport.

The traffic was real. The missed shuttle was real. The security line was real.

But the stress? That part was on me. I had left myself no margin.

Had I missed the flight, I would have been flying standby with no guarantee I would make it to Baltimore.

The trip was for a mere 48 precious hours with them.

My plan left no room for obstacles that were out of my control.

Planning our travel day may be just as important as what we pack. Maybe more so.

I didn’t do that.

I should have left 90 minutes earlier.

When flying, it’s better to be early. The phrase, “better late than never” doesn’t apply to air travel.

And if you have extra time at the airport before your flight, get a cup of coffee, read a magazine, people-watch, or just scroll through your phone like the rest of us.

Starting your trip without that unnecessary stress will be worth it.

Trust me on this one.

Sometimes it takes an unexpected event to have you re-evaluate your choices or decisions.

If you have followed our journey in New Zealand, you may know what I am referring to.

Rental car insurance.

I have rented cars many times over the last 35 years.

If I was traveling for business, I would follow the company policies. If the policy required taking the insurance, I did. If not, I didn’t.

But for personal travel, I have never taken the insurance. I have never needed it. What were the odds I would need it this time?

My car accident in Ashburton, New Zealand has changed my view.

I was fortunate my credit card company investigated the incident and later reimbursed me for the cost of the damage to our rental car.

But reality is, I was lucky.

The credit card I (haphazardly) chose to use had travel coverage. I could have easily pulled out a credit card that didn’t have that feature.

Details are everything when it comes to situations like mine.

I read the card’s travel insurance features after the accident. Even with my legal education, I wasn’t sure if I was covered.

I said a prayer and wished for the best.

My new personal rule is simple: before I decline the rental car company’s insurance, I need to know exactly what my credit card covers, what my personal auto policy covers, and what exclusions may apply.

If I cannot answer those questions with confidence, especially when traveling internationally, I am much more likely to take the coverage offered at the counter.

And I am now rethinking whether I should be buying travel insurance. The research has begun and I’ll report what I find.

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

My most recent blog entries chronicle our trip to New Zealand, including Queenstown, Milford Sound, That Wānaka Tree, the lupins, a car accident in Ashburton, and a moving visit to the Gallipoli Exhibit at Te Papa.

The cruise with my wife, stepkids, daughter, son-in-law, and grandchildren is right around the corner. I am looking forward to sharing some of the lessons we learn traveling as a multi-generational family. Stay tuned!

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

I’ll see you back here on July 15.

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

—Stephen

​

​​