My 5 Biggest Travel Mistakes And Mishaps

Nomadic Matt asked for biggest travel mistakes in a tweet, and it occurred to me that I have several of my own – that I’ve shared in one form or another – but that it would be a good idea to highlight because even though I ‘know what I’m doing’ I’m far from perfect.

In fact with the number of times I run into problems with airlines making reservations or dealing with changes, I often wonder how the median passenger even manages to get from A to Z.

All of mine worked out fine, with airlines and hotels going above and beyond to accommodate.

  1. Showing up at the airport in the afternoon for a morning Sydney – Los Angeles flight Virgin Australia had changed the flight time months earlier, which at some level I knew, but Delta (who issued the award tickets) hadn’t notified me of the change. Delta re-booked me onto their own non-stop the next day in business class (revenue inventory) and Virgin Australia gave me a hotel room for the night.

  2. Snuck into a United Airlines club lounge when my ticket would have granted me access, only I didn’t realize it. That was over 20 years ago and I still feel rather dumb for it.

  3. Showed up at the Novotel Bangkok Suvarnabhumi hotel only to learn I’d made a reservation for the following month they simply moved my prepaid booking ahead.

  4. Drove to the wrong Hyatt in Miami out of sheer habit, I’d simply gotten used to staying at the Hyatt Regency Coral Gables. To save me the hassle of changing hotels they simply transferred my booking and I wasn’t treated as a no show at the other property.

  5. Let my AAdvantage miles expire when I was a teenager. I’d accumulated about 20,000 miles from a trip to Australia (I flew American back when they served Sydney via Honolulu with a DC-10) and when I went to credit a trip to Florida I learned my account was no longer active. I didn’t re-join the program for about 5 years, and though it wouldn’t benefit me in any way I still wish I had my original account and joining date.

What are your biggest travel mistakes and mishaps?

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Went to the wrong airport in DC. Flew in to DCA and didn’t realize my flight home was out of IAD (ticket booked on Travelocity). Showed up at DCA and the agent said I was at the wrong airport and on a cheap fare. She actually rebooked my flight out of DCA but I had to sit for six hours.

    Used a pile of membership rewards and bought my son a Sony PlayStation. I didn’t know anything about the points and miles game back then.

  2. Showed up at DCA instead of IAD or returned into a different WAS airport from where my car was parked. I’ve done both more than once!

  3. I had a free weekend during a business trip to Manila, and decided to spend it in Saigon as a tourist. I didn’t check, but US citizens need a visa to visit Vietnam, and I was informed/refused at the Manila airport check-in counter. I did a “backflip” to sign up with a Vietnamese visa agency, get passport photos taken, and pay with lots of extras to get a visa expedited and lined up for my arrival in Saigon on a subsequent flight about 4 hours later. In the taxi from the Saigon airport to the Hilton downtown I remembered I had a valid German/EU passport in my briefcase which I never use – but could have used to board my original flight. Duh!!!

  4. Had a bus class award ticket from BA to IAD, i thought flight left thurs pm but was actually 1am thurs am (eg wed night departure from hotel to airport) Fortunately we realized in time and used the hotel room we had prepaid for to rest and nap before heading to airport.

  5. 2009: Showed up at the Hong Kong airport a day early for a flight to Helsinki. I was on an around the world trip booked through American and I kept getting flight change updates, all which I though were just minor time changes. I did not realize in addition to the time changes, the flight to Helsinki was changed by an entire day. Wandered around the check in area looking for Finnair to no avail. Finally asked the help desk who directed me to Dragon Air (subsidiary of Cathay Pacific) for help. Unbelievably the very kind Dragon Air woman rebooked me on KLM via Amsterdam–a completely different alliance! My ATW ticket was paid business class, and while I sat in very old KLM business class I earned no AA points/miles for that stage. I did get to Helsinki on the day I was supposed to though. I also got once of those souvenir houses filled with brandy that KLM gave out to business class passengers.

  6. I just got into points right before going to college. Took a trip to Japan using Avios I think before a big devaluation. Still had a lot left but thought because I didn’t have enough for a big trip like Japan I woudl never use them. Didn’t realize you could use them for domestic flights. Ended up using a bunch for a 1 night stay at an okay hotel in NYC.

  7. Did something similar in Australia, but with Qantas , booked the wrong dates , because of date format , booked July 6th (7/6) instead of June 7th (6/7) and at the airport they all had a quick laugh and put me on the correct flight , no change fees , no problem.
    Could you ever imagine that happening in the US ?

  8. For 2 1/2 years, my wife and I lived in Rio d.J. while I was working for a large tech company. My territory was everything south of the USA.

    This meant that my travel was bizarre and beyond what most would understand.

    One of those fights. I was running late for a flight to Panama… so late that when got to the counter they told me to run to the gate. And I made it, with them closing the door behind me.

    The next day, at the gate in Panama the agent asked for: ticket, passport, yellow fever certificate.

    Being in Brazil, I was vaxed like crazy… but not against yellow fever.

    The agent stated that I could not go to Brazil from Panama without it, and they should not have let me leave to Panama from Brazil without it.

    I had stated that I had been in Panama many times, connecting and going to other countries. And he said: Yes, but you were going THROUGH Panama, not TO Panama.

    His solution: he would send me to a hotel for the night (gratis) and booked me the next day to Costa Rica.

    I was confused and upset: why the hell would I want to fly to Costa Rica??!!??

    He said that way he could say that I flew TROUGH Panama. And Brazil would be fine with that.

    Of course, my next question was: Why don’t I just SAY that I was coming from Costa Rica? But he would not accept that as there needed to be a paper trail.

    Finally, more than a day later, I get back to Brazil. Walking off the plane there was a a very old and tiny woman that asked: “Yellow fever certificate?” And I answered: “I was coming from Costa Rica”. She said “OK.”

    24+ hours of my life for: “OK.”

  9. Driving to the wrong Hilton in Scottsdale is easy to do. There are two Hilton resorts on Scottsdale road within 1 mile of each other (a google check shows 0.9 miles). Hilton Doubletree Resort and Hilton Scottsdale Resort and Villas. They are both on the east side of the road.

    I’ve gone into the wrong one to check in at least once.

    Not that it matters, but we generally go to the Doubletree one, maybe because of the cookies? Or because it tends to be a few $$$ cheaper and the rooms are pretty similar IMO (std room)

    I don’t recall any major flight issues but I once had to fight AA because they had the wrong time in their computers (they weren’t handling time zone issues correctly) and I would have had less than 1 hr to change terminals at Heathrow (going from BA europe flight to AA flight to return to the US).

    Eventually I got hold of an agent who checked further and realized the situation and moved me up to the earlier flight. It pays to check your flight times.

  10. Bought a (great deal!!) tkt to San Jose CA thinking San Jose Costa Rica. My travel companions had to clue me in when using my itinerary to book their own tix!

  11. As a young lawyer in the 1990s representing an investor on a transaction in Belarus, I flew into Minsk without realizing I was supposed to have procured a visa in advance. While the immigration official was dressing me down and ordering me to get back on the plane to Frankfurt, my Belarusian contact (who in hindsight I should have known was a member of the intelligence services) walked right through security past the armed guards and yelled at the official who, tail between his legs, issued me a visa on the spot.

  12. @Glove. God, I’m with you. As a DC resident I have actually done the same a few times. Mostly I just head to DCA (my preferred) and realize when checking in that my booking was out of BWI. I have a feeling if you live here for years it’s a bit more common than we think. And yes, like you, I was also once able to snag a last minute Club World seat to BWI with points and come home two days early. As I was sitting on the plane it occurred to me, “OMG, I drove to Dulles instead of taking Uber for the outbound! My car is at Dulles!!”

  13. Left my hotel in Vienna in plenty of time, sure I knew how to use the subway to the airport, and got on a train going in the wrong direction. When I finally made it to the airport, the ticket agent went into hysterics that I was too late for my flight, apparently I was the first in Vienna. Nevertheless I got a flight out the next day at no additional charge.

  14. All-time worst travel mistake: In the fall of 1966, as a 19-year-old exchange student from U.C. Berkeley to the University of Sussex for 1966-1967, I began my great adventure with some east-coast couch-hopping. Everything was going well. My United 707 flight SFO to BOS landed in record time (according to the pilot) because of super-strong winds aloft. My evening flight BOS to JFK was intentionally booked on an Eastern Airlines Connie, rewarding me with a view of fabulous piston-pounder exhaust plumes against the twilight horizon. All ground connections for this nearly penniless traveler were, of course, by public transport. I was staying with an English banker friend of my parents in his swank Manhattan apartment. I was caught off guard by daytime traffic from there to JFK, and pushing my loaded cart at break-neck pace from the bus terminal, arrived at the Pan Am terminal only to watch my flight, out on the runway, take off without me. Facing a year away from home I was traveling with two heavy suitcases, a carry-on, and a guitar. Good news: the kindly Pan Am folks booked me on a 707 Quantas flight due to board shortly. Bad news: the Pan Am and Quantas terminals were as far apart as any two terminals could be at JFK. I piled my kit back on my luggage court and again at break-neck pace pushed the mile or so to the Quantas terminal. It was near 100 degrees and I arrived fully clothed as if I were stepping out of a sauna. Aussies tend to be a relaxed tribe, so despite being a sweat hog I was taken under the Quantas wing and soon was on my way to London. A dumb start to what turned out to be a watershed year in my life. I continue to look kindly at all things Australian — even when, in my younger days, I was playing rugby against the brutes! I played rugby much better than I played my how-cool-am-I guitar. But both were good for my dating life!

  15. I had a flight to St. Louis from Newark, but thought it was from LGA. Luckily, it was an early Saturday morning in October, and a taxi took me from one to the other in about 45 minutes, including both tunnels. It only cost a little over $100.00, and I gave the driver an enormous tip.

  16. Showed up at JFK for an Aer Lingus flight to Dublin … from Newark. I couldn’t figure out why the Dublin flight was at 6:10 when my ticket said 6:30. Non refundable discount business class ticket and the agent changed the routing for free.

  17. Showed up at 7:20 am at LGA for an 8 am flight and they refused to check me in because I left my ID at home (pre 911). I ran out and found the same can that just dropped me off and told him I’d make it worth his while if he could get me to Manhattan and back in 30 minutes. Half our later and 50 bucks poorer I checked in and boarded the flight as the door was closing.

  18. On my honeymoon, daylight saving started the morning of our return flight. Keeping track of that never crossed our minds, and when we got to check our luggage, we found out flight left 15 minutes ago. They put use on standby for the next (full) flight, and luckily someone else must have also forgotten about daylight savings time, so we cleared onto that flight. I think it was on Eastern Airlines.

  19. Had a complicated itinerary where the wife would come to join me in FCO, and she’d fly straight back with AZ and I’d take the cheap ticket with AF. Only, when we got to check-in, I didn’t exist. Only after some scrambling did I figure it out: the AF/KLM site by default gave a return trip two weeks after the outbound one. So, in the last iteration, I failed to set the calendar back a week, and now, my $100 non-refundable return ticket was for the next week.
    The guy at check in was at least cool enough to suggest that there was availability on some direct flights by other carriers (wink wink) that would be quite reasonable.
    So, I got in the AZ line, got on the internet, and had booked a last-minute, 1-way business class fare for less than economy ($200), on my wife’s flight.
    Of course, she got the upgrade.

  20. I was flying from my home in California to Berlin. I slept only a couple hours the night before I left and woke up late. Panicking I grabbed my luggage and called an Uber. It wasn’t until I was in line to board the flight that I realized I had forgotten my glasses. I could read almost nothing without them.

    It just so happens that my glasses are German and their factory store is in Berlin. So visiting that was an unexpected treat. They took care of me and I was wearing new glasses the next day.

  21. I am terrible at doing the 24 hour clock translation. Terrible. I cannot count how many times I’ve been in Europe or Asia and told myself my flight at 14:20 was at 4:20, etc., etc. My worst story involves making this mistake in Frankfurt. I was fairly new to the points game and had proudly booked a flight on Lufthansa in F. I’d flown into Frankfurt the night before after a trip to Vienna and stayed at the airport Sheraton so I’d be able to spend plenty of time being wined and dined in the luxurious Lufthansa first class lounge, and driven to my plane in style. Well, as I was lazily packing my bags in my hotel room and wondering if 3 hours early was too early to hit the lounge, I had this funny feeling that I had made that time mistake (again) and grabbed my ticket. Sure enough, my plane was boarding and leaving in less than an hour. I dropped my key off at the front desk and ran (as fast as one can with a large suitcase and carryon) to the Lufthansa first class desk. They ushered me (in person, no car) through security and I ran all the way to the gate an arrived at the plane sweating and just grateful to have made the flight. Sigh. I have yet to see that wonderful lounge.

    I now have a cheat sheet laminated in my wallet. On one side is the translation any 5 year old can make for the time difference (13:00 – 1:00; 14:00- 2:00 . . .) and on the other is the translation of Fahrenheit to celsius so I can figure out whether the hotel thermostat is broken or it’s just that 20 degrees is fricking freezing! And, I now triple check the time on my ticket if it takes off any time after noon.

  22. My husband and I got engaged in July 1985 and planned our wedding for the beginning of November. Almost all of the planning fell to me, including booking our honeymoon. We, or perhaps I, decided that Barbados would be nice as I had heard good things from friends. My husband, who sold advertising to local businesses, suggested a travel agency only a few blocks from my office, since I had traveled more than he ever did (which was almost never).

    The day after the wedding we arrived at the airport, all smiles as newlyweds. This was back before online anything, so we were just getting seats assigned at check in or the gate – too long ago to remember that detail. Our luggage had already been tagged and taken. As I waited, the agent’s eyes grew bigger and bigger, and her frown lines deeper and deeper. Finally, despite my holding the paper tickets, she informed me we were not on the manifest and the flight was full! Tears started to slowly run down my cheeks as I tried to remain calm. She managed to book us on a competitor airline departing about 2 hours later so we had to scramble to change terminals at JFK. We arrived in Barbados to find our luggage left off to the side in the fairly empty terminal – luckily it was there!

    When we arrived at our hotel, they, too, did not have our booking for the week, but they gave us a room and said they would work it out for us. 3 days later there was a big government conference that filled all the remaining rooms. We later met another couple who arrived at that time and were moved to a smaller, lesser property down the beach. Luckily we were able to stay.

    Coming home there was a major problem at the airport with flight delays and all kinds of commotion, but we eventually got on a flight and came home. And we are still married almost 36 years later! (needless to say, I found a new travel agent back then.)

  23. Flew to Portland Oregon when our holiday was in Portland Maine.

    Only realized when the captain told us what time it was when we landing.

  24. Twice bad visa issues that kept me from Shanghai. One trip was over, but the other one was quickly recovered so I met the Etihad A380 First first time 🙂
    Have now decided not to go to China, so there’s that 😉

  25. Vacationing with my daughter in San Sebastian, Spain, she thought it would be a good idea to put the passports in the hotel room safe. I have never used a hotel rooms safe before and always kept my passport in my laptop bag. Naturally, we left the passports in the safe when we left by train for our fly point of departure, Amsterdam. We were just beyond Paris when we realized our error. We continued on and sought help from the management of the previous and current hotel. The GM of the San Sebastian hotel retrieved the passports from the safe and faxed a copy to the manager of the Amsterdam airport hotel. Our flight was 11:00 a.m. the next morning. We hired a car for the morning and arrived at the U.S. Consulate at 7:30 a.m., one half hour before opening. We beat another person with the same idea by three minutes. They opened promptly at 8:00 a.m. and expedited a temporary passport. The faxes were a key assistance. But we had to get pictures made at the nearby drug store. We ran over there only to find that they opened at 9:00 a.m. We banged on the door and begged them to open early for us. They accommodated with a 10-minute early opening. Pictures taken, back to the Consulate where the passports were all ready except for the pictures. We headed back to the airport in our hired car. My daughter went to the airport attached hotel to pick up the luggage and I went to check-in and let them know the situation. When she showed up with the luggage, we completed the check-in process and headed for security. We made it to the plane with a good five minutes to spare. I usually don’t drink when I’m flying internationally, but this day we celebrated our good work with the help of many with a couple of very cold bloody marys.

  26. There are (or were) two hotels in NYC with the name The NoMad. My daughter was a chef at the original NoMad, which gave the name to the North of Madison neighborhood. I was coming home from Iceland and had missed my flight home. I checked on one of the last night booking sites and found a really good rate for the NoMad. Booked it, but when I arrived at the hotel, the desk couldn’t find my reservation. I looked back at the booking and saw that I had booked The NoMad
    St. James, about three blocks away. I stayed there, and it was pretty nice, but not the right NoMad. A few months later, my wife and I went to NYC to see my daughter. This time, I intentionally booked the NoMad St. James because it was much less expensive than the original NoMad. Got there, no reservation. I had booked the other NoMad Hotel, the one that I had wanted on that first trip. How could I mix up the NoMads twice? That hotel has now closed, which is a shame, because it was terrific, especially the restaurant. But my daughter is going to be the Chef de Cuisine at a new restaurant at what looks like a fantastic new hotel opening in midtown Manhattan. It’s going to be called the Pendry. We are going early next year, and I doubt that I can confuse that name with another Pendry.

  27. I had a flight from NYC to WAS and landed at IAD assuming return flight is from IAD. Didn’t realize the mistake till 5am on the day of the flight, where flight leaves at 8:15am ET and I am at Hilton near IAD. I also had Hertz rental to be returned at IAD. I at once checked out at 6am and went straight to Reagan international and returned hertz at that location (lady was surprised at the counter asking if I did intend to really return it here while it says IAD) , told the lady I really wish to return it at reagan international( she didn’t charge anything extra) and then boarded the flight back to NYC via philadelphia. Last minute on the jetway realized I had left bag at TSA and ran back but when I returned, flight had closed already! So they rebooked for the next flight 6 hours later free of charge!

  28. When Shanghai Airlines (FM) was still a *A member, I’d booked an award ticket using UA miles to fly from Shanghai to Hong Kong. Out of habit, I’d assumed that the flight would be out of Shanghai Pudong (PVG) airport, so I got there only to find out that the flight would be out Shanghai Hongqiao Airport (SHA). I still had 1.5h to make the flight and hopped in a taxi, but a huge downpour that day brought traffic to a crawl and made me miss the flight. To make matters worse, UA had reserved the award flight but not ticketed it! To rectify the matter, FM charged me a $100 USD fee that United agreed to reimburse me (and did), and I was able to make it to HKG on the next FM flight two hours later…

  29. Back in 1990, vacationing in HI and lost track of what day we were flying home. Got a phone call from hotel’s front desk asking if we were staying an additional day. Got to rental car return, checked in and asked them to hold the plane and then with wife, ran the length of the concourse with 2 yr old and car seat in tow. Made it somehow.

  30. Similar to the IAD/DCA mix-ups, Chicago version: Thirty-some years ago I drove to ORD and flew out on business, booked to return in time to put my kids to bed Friday night. My return flight was grossly delayed, but I managed to grab one of the last seats back to CHI on an earlier flight. Only when I was in the air did I realize that while I was headed for MDW, my car was at ORD! My kids were young enough to think that the CTA trip to ORD was the greatest thing to do on a Saturday morning. Not sure that was a mistake as I did get home in time for their bedtime.
    One more: Also long ago, we were booked on award tix to fly ORD-FRA-AGP departing Dec. 24. Showed up at a practically empty ticket counter several hours in advance, handed our paper tickets to the ticket agent, who stared at them a very long time, starting playing with his computer and announced that the ORD-FRA 12/24 flight had been canceled back in October, and somehow we hadn’t been notified or rebooked. (My mistake was not checking with United on status periodically – but I’m not sure they had a website back then.) It took the agent over an hour on the phone and computer, but he rerouted us ORD-DUS-hotel in DUS for Christmas Day, DUS-FRA-AGP 12/26. We had a good time exploring Dusseldorf and Karlsruhe, but I would have preferred the time on the Costa del Sol.

  31. At the end of a delightful three-week tour of Italy by train that started in Milan, I mistakenly booked my last two nights in Rome for the following month. The perplexed desk staffer could not understand why my res wasn’t coming up, then informed me I wasn’t due until 30 days later. Although the rate was higher, the hotel kindly agreed to honor the lower rate booked through AMEX Travel and all was well before returning to US.

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