5 Travel Mistakes We Wish We Had Been Warned About

Updated: Mar 14


Travel Mistakes

We’re pretty savvy travelers, but we’ve made our share of errors. Sometimes it was our fault and sometimes just bad luck. Had we had known about them ahead of time, we might have avoided a few problems. Here are some lessons we learned from travel mistakes we wish we had been warned about.


1. Double-Check That Passport


When Jess was living in Copenhagen, Doug and I decided to meet her in Croatia for vacation and then return with her to Denmark to visit. For some reason, I was holding all three passports on the flight to Denmark. When we landed, I handed Jess her passport – or so I thought.

Travel Mistakes

Several days later, Doug and I hugged Jess goodbye and set off for the airport to go home. When I presented the passports at check-in, we discovered to our horror that I had given Jess Doug’s passport by mistake. We frantically tried to reach her by phone so she could deliver it to the airport, but she was asleep and never heard the calls.


Our flight left, so we had to rebook to leave the next day. We taxied back to Copenhagen, and checked back into the hotel we had just vacated. While it was nice to see Jess for one more evening, it was one very expensive travel mistake.


2. Have at Least Some Essentials on You


While on a cruise to Bermuda, I decided to sign up for an excursion to swim with dolphins at a dolphin sanctuary called Dolphin Quest. The literature warned us not to take anything with us except for a towel, so I duly followed directions. Little did I know that not only did I have to take a ferry to the other side of the island to get to the sanctuary, but that my designated time for dolphin swimming was two hours from landing.


I had nothing on me except for two American dollars and that towel. No cell phone, no credit card, no sunscreen. I wandered around the area (it’s part of the National Museum of Bermuda, situated in a fort) for those two hours before presenting myself at the dolphin sanctuary. By the time I got there, I was thirsty, hungry, and sunburnt. I did greatly enjoy the swim experience. The staff also took pity on me and kindly gave me photos since I was unable to buy any. It’s a good thing the return ticket on the ferry had already been paid for.


3. Make Sure You Know Your Meeting Place


We took an organized bus tour from Madrid to the town of Segovia, known for suckling pig and its ancient Roman aqueduct, a UNESCO heritage site.

Travel Mistakes

We were so intent on getting into town that we didn’t pay attention to where the bus parked when we were dropped off. At the designated departure time, we walked over to where we thought the bus would be only to find the area empty. It turns out we were only off by several blocks, but we didn’t know that. After 45 desperate minutes looking for the bus, we perched Doug and Jess along the road leaving town to try to flag the bus down while Bobby and I went to the local police station for help. Luckily, the bus had waited those 45 minutes for us, and Doug was able to stop the bus on the exit ramp. Embarrassing and potentially disastrous.


4. Pack Some Clothing in Your Carry-On Bag


This is one of the most common travel mistakes. I made a connecting flight to Milwaukee, but my suitcase didn’t. I had no spare emergency clothing in my carry-on. Plus, I was traveling for a business meeting; showing up in my jeans and T-shirt was not the image I wanted to convey. I ended up rushing out to buy a few basics to get me through. I now pack at least a few pieces of clothing and some toiletries in my carry-on just in case this happens again – which we all know will.


5. Secure Those Windows


One of the hotels we stayed at in Costa Rica is the beautiful Peace Lodge at La Paz Waterfall Gardens in the rainforest. The rural area boasts all sorts of wild animals; the hotel itself has a small zoo of some of the local fauna, such as parrots, jaguars, and monkeys.

Travel Mistakes

Bobby and Jess had a ground floor room. They left the windows open when they went to bed. It happened to rain overnight, no surprise in a rainforest.


When they awoke, they discovered they had had a sleepover with one of the Lodge’s house cats, which came in through the open window to seek refuge from the storm. While the episode was funny, it could easily have been a wild animal that decided to spend the night indoors with them. That would have made for a crazy addition to our list of travel mistakes.


We hope these travel mistakes that we wished we had been warned about help you avoid some travel snafus. Have any other advice or want to share your stories? Send us a message at info@winewithourfamily.com. Always feel free to reach out to us with any questions or feedback.


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