
After 30+ years of traveling seven continents, and more than 50 countries, we consider ourselves to be “experienced” travelers. You would think by now that we had it all down to a science and know exactly how to successfully navigate travel. Well, we still make mistakes. We see travel as a continuous learning process, especially now. We wouldn’t say that we’ve made every mistake ever made… but we’ve come pretty close.
We hope you’ll enjoy this journey through our travel mistakes and even add one or two of your own.
1. 25 Cities In 20 Hours (Or Trying To Do Everything)
Reggie’s first trip out of Singapore right after she graduated college was one of those bus tours of Europe where you go to 20 different cities in a very short period. In some ways, we’ve never grown out of that. We always try to do too much everywhere we go, especially if there is street art to be seen.

2. Passport Mistakes
Bringing an expired passport or one that has less than six months validity is such a common error. We each have made this mistake at least once. One of us was flying from the U.S. to Canada on a business trip, thinking she only needed a driver’s license. Another time, one of us brought an expired passport. Since we left for the airport very early, we had time to go home despite the rush hour traffic and get the current one.
3. Leaving Too Late For The Airport
This is the only mistake on this list that we don’t make. For an international flight, we often leave at least three hours ahead of boarding time. Since we live in the New York City area, it can often take two hours just to get to the airport. This came in handy when Sue brought her expired passport accidentally.
4. Disagreeing About A Destination And Going Anyway
One of the most problematic mistakes we ever made was deciding to go to a destination that one of us disagreed about. It involved driving 14 hours round trip to a volcano in rural Tanzania. Neither of us ended up enjoying that part of the trip and we never made it to the top of the volcano.

5. Not Having The Right Clothing Or Gear
We have made this mistake so many times we can’t even count. When we went to the Atacama Desert, we didn’t pack enough warm clothes and ended up wearing every piece of clothing we had brought to try to stay warm at the geysers. In Alaska, we checked the weather beforehand, but it was unseasonably cold. In that case, we went shopping.

6. Bringing Too Much
Given the experiences we’ve had, you might think that we never overpack. In our early travels, we packed very light. We did three weeks in Asia with just carry-ons. As we’ve gotten older, we’ve become more used to having some conveniences. I once went on a trip with my mother to Ecuador and she brought two huge suitcases for a 10-day trip. I asked why she brought so much stuff. She said she didn’t know what she would want to wear on any particular day, so she made sure to bring everything.

7. Not Knowing Where Your Gate Is Located
Okay, this one probably seems like a no brainer. Find your gate. Then go relax somewhere nearby. In Norway, we were walking through the airport and saw a nice-looking restaurant for breakfast. The sign implied that our gate was just down the hallway. We never looked how far down the hallway it was. We had a leisurely breakfast. When we heard the boarding announcement, we started walking to the gate. We soon realized that the hallway was very, very long. We started running and finally arrived at the gate at the last call.
Gates also change periodically, make sure to check periodically. If you do not speak the language, you can really run into trouble. Make sure you are waiting close to the gate unless you want to test your 100 yard (100 meter) dash speed.
8. The Layovers, Layovers, Layovers
Layovers are a constant struggle. They are either way too long but not long enough to leave the airport. Or they’re too short. We hate the anxiety of not knowing whether we’re going to make our flight, so we often choose a longer layover. That can be particularly challenging when we’re going to Asia and a 21-hour trip becomes a 28-hour trip. Sometimes we just add in a stopover in Taipei or somewhere else to break up the journey so that we don’t have to worry about the layover.

9. To Travel Insurance Or Not To Travel Insurance
People have conflicting opinions about travel insurance. We always get travel insurance. If we are going somewhere off the beaten track, we buy medical evacuation insurance. We’ve had friends that had to be medically evacuated and because they had insurance, dodged a $100,000 bill. To us, it just seems worth it not to have to worry.

10. Not Knowing The Visa Requirements
Understanding visa requirements through your own research is critically important. We travel on different passports. One of us is a U.S. citizen and the other is Singaporean. There are very different rules in every country for both passports. Once, we were in Peru and crossing over to Bolivia at a tiny passport control station. Our travel agent had told us that Singaporeans didn’t need a visa. We trusted our travel agent and did not do independent research. When we got to the passport control station, we ended up having to pay to get across the border. We still don’t know if that was legal or illegal.

11. Making Calls From Abroad
Have you gone on an international trip and came home with a huge cell phone bill? Not turning off roaming data when you travel internationally with your cell phone could run you up a bill even more than the cost of the trip itself! These days, we use apps that allow us to communicate locally. We also travel with unlocked phones where we can easily swap out our SIM cards for the local ones to keep our cell phone bills low. Remember to swap out the SIMs when you return home.

12. Converting Currency And Other Things
Understanding how currency and weights are converted is important when shopping at the markets, at the airport, at the bank, and doing anything with cash. Airports have the worst conversion currency rates. Some local cash conversion places will also try to get over on uninformed tourists. Once we were in Mexico buying cheese (in kilos). We did the conversion in our heads from pounds to kilos and ended up with four times more than we wanted.
13. Not Doing Your Own Independent Research
Doing your own research is so important for a relaxing, enjoyable, and safe trip. We have relied exclusively on what a travel agent had told us many times and then found out that it wasn’t 100 percent accurate. For instance, in our attempt to scale Ol Doinyo Lengai, the travel agent told us that we didn’t need any special equipment. That was not the case and we could’ve easily figured that out if we had done our own research.
14. Not Trusting Your Own Instincts
Over the years, we have learned to trust our own instincts. When we saw the boat captain in Southern Laos bailing out water from the boat that we were supposed to get on, we refused. It did not seem safe to us. That meant waiting hours longer for a boat that wasn’t leaking. Our guide was not happy with us but we felt safer.

15. Not Understanding The Culture
We value being culturally respectful wherever we travel. It’s important to have some understanding of how to behave and dress in different countries and at religious sites. For us, there’s another layer. As an LGBTQ+ couple, we also need to understand how to be safe as well as respectful. We’ve traveled in many countries where being LGBTQ+ is illegal. We have learned how to navigate hotel rooms, nighttime activities, and other issues like public displays of affection (which we mainly avoid).
There are so many more mistakes that we could mention here, including failing to notify your bank and credit cards about travel plans, not sharing copies of your itinerary, understanding time zones, ending up at the wrong hotel or the wrong airport, and more. The COVID pandemic adds another layer of complexity.
We are sure we will discover some new mistakes to make in our next decade of traveling.