TRAVEL REFLECTIONS

Oops! That Was Stupid

A small collection of self-induced travel blips

Photo by JESHOOTS.COM on Unsplash

I’ve traveled a lot over the decades for business and pleasure. While most trips were meticulously planned, there were times when things would go wrong.

Weather, mechanical delays, illnesses, and last-minute changes can disrupt a trip, but these issues are resolved by adjusting flights, modifying schedules, or making a few phone calls.

However, sometimes I overlooked a planning detail or two, which created situations I hadn’t anticipated. All I could do was laugh, slap my forehead, and say, “Oops.”

Everything usually worked out in the long run. Here are a few things I did that I take 100 percent responsibility for:

• On a trip to Cozumel, Mexico, I accidentally tipped the concierge $50 instead of $5. This was in 1979, and $50 was a lot of money, especially in Mexico. I got confused about the dollar-to-peso conversion. Throughout our stay at the resort, we were treated with extra care. When I figured out what I did, all I could say was, “Oops, that was stupid!”

Photo by The Travel Nook on Unsplash

• On a family trip to Yellowstone National Park in the early 90’s, we flew into Denver and drove to Yellowstone. Then we drove across Northern Wyoming to South Dakota to see Mt. Rushmore and the Badlands National Park. What I didn’t plan for was that when we ended up in Sturgis, South Dakota, for lunch, it was the height of the annual Sturgis Motorcycle Rally. It was fun for me, but surrounded by Harleys and bikers, it was not a good place to be in a minivan with two young kids.

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• On a business trip to New York City, I got on the wrong subway. I needed to go to Brooklyn. Instead, I ended up going the opposite direction. The irony behind the mistake is that the Metro Transit Authority was my customer. They manage the subways, commuter rails, and bus systems for NYC. My contact had given me specific directions to ensure I didn’t make the mistake I did.

Photo by Mitchell Trotter on Unsplash

• One afternoon, I had a flight to catch and fell asleep in the terminal. When I woke up, the area was empty. Panic set in quickly, but after speaking with a customer service agent, I learned that my flight had been canceled due to a mechanical issue. All passengers were transferred to another plane, with a new departure time in three hours at a different gate. Fortunately, I was upgraded to First Class, and it’s the last time I ever took over-the-counter medication for a sinus infection.

Photo by Phill Brown on Unsplash

• On one of my trips to New York City, I had an afternoon off. I decided to go to the top of the Empire State Building. I took the train from Newark to Penn Station. When I got streetside, I immediately spotted the Chrysler Building and walked to it, thinking it was the Empire State Building. It turns out it is a common tourist mistake. The security guard at the Chrysler Building was nice and pointed me in the right direction.

Photo by Todd Quackenbush on Unsplash

I have friends who have traveled more than I have. Their stories are often similar: many trips without any problems, followed by one trip where multiple things go wrong. It’s all part of enjoying life.

Thanks for reading.

© 2026 All rights reserved, LJ Bentch