The 5 Biggest Travel Mistakes I’ve Ever Made

I do pretty well in travel but also make my share of mistakes, mostly out of habit or path dependence. Since I know how things ‘usually work’ I don’t always pay attention to schedule changes. And I don’t pay attention to the details of my reservations – I’m on auto-pilot, I know that when I land in a given city I ‘always’ go to the same hotel. If I booked a Hyatt there, it must be my usual one!

Here are the (5) biggest mistakes I’ve made in travel, though each one worked out just fine. I thought I’d share these to show my own fallibility, I know the correct advice and should always follow it but I am… human.

  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when they served Sydney via Honolulu with a DC-10) and when I went to credit a trip to Florida I learned my account was no longer active.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 dumb or absent-minded things have you done?

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, 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. Reserved an Avis car at the Portland, ME airport when I meant Portland, OR.

    I discovered my mistake when I rolled up at PDX. The desk crew shrugged and set me up with a car anyway. All good until a giant bill arrived in the mail from Avis a couple of weeks later. They had left my PWM reservation intact, rented a car to someone else using my name, and that other driver wrecked it. Avis insisted I owed them $4,000. It took weeks of pleading with a parade of Avis reps to convince them of their error, which of course resulted from my error.

  2. Had a flight from LHR-DEL at 20:35 so I was sitting in the lounge at 9:30p when I decided to head down for my 10:35p flight when I noticed it was not on the board: a cold streak of panic kept through me.

    How could I be so stupid!

  3. Boarded the wrong Peoples Express connector out of Newark. Instead of Boston, ended up in Pittsburgh. To make matters worse, I didn’t have the cash to pay for the flight, only had enough on me for the Boston flight.

  4. Usually fly Southwest for short haul and Delta for longer flights. Booked a United flight last minute because of schedule and cost. Went to airport and tried to check in and print a boarding pass at Delta self service kiosk. Reservation was not popping up. Friendly agent noticed I was having difficulty and walked me over to the desk Asked for my ID and could not find me in the system. She asked to see my mobile boarding pass, so I handed it over and she kindly said “Sir your flight is on United. You will need to check in down the hall from here”
    Oops… =)

  5. Miscalculated door close time on a JetBlue flight out of JFK. Went to BeRelax and got 30 min massages. Arrived at gate for final boarding call and made it on thank god.

    Took a one way rental but accidentally booked as 2-way and didn’t check before I dropped it off. Got hit with $200 fee. (I made the reservation after my flight landed when I saw the price of Uber)

  6. In CPT a few years ago I deliberately made white shark cage diving my final day activity, as a bit of a way to cap off the trip. Wind on the ocean caused the trip to be cancelled and I had to leave the next day.

    When possible, schedule the highlight of a trip so you can recover with a plan B.

  7. My opinion is statistics. X number of people no show for flights/rentals/hotels every day. Safe to assume most people miss flights by accident. The more often you travel the more likely you are to miss a flight. Especially considering the fact that frequent travelers are less obsessive with checking on their reservations. Anyone that travels often has miscalculated times, showed up to the wrong airline, booked for the wrong day etc.

  8. MANY years ago, when there were only paper tickets, mom took me to lunch so I would be fed before my 1:20 flight – in the days where you just checked in and walked to the gate- when I got there the skycap wouldn’t take my checked bag- why? because the plane was leaving at 12:20 and the second two was blocked out on the crease- tried to run to the plane- missed it and United was going on strike at 5pm- sheesh- but made the next plane- last standby seat- no problem putting my bag up in the overhead bin and avoided missing a special weekend.

  9. This was just after 9-11. I was lecturing at the FBI Academy at Quantico (it is on the USMC BASE) and flew into Dulles. I had reserved a compact car to pickup at 11pm. Well Budget read that as Compact Pickup (truck). Not only that but it had a covered bed. The base was at FPCON Charlie so extremely heightened condition. It was after midnight when
    I arrived at the front gate. Full documents check and underbody search with mirror and dogs. They asked me to open the bed and I had no idea. Calling. Usher’s a dead end as they were closed at the Dulles facility. We were going on 90 minutes at the gate and finally a marine was found that owned a similar vehicle and got it open. No one thought to look in the glove box for the owners manual either. Finally got to
    My room and rack at about 0300. Luckily I did not lecture till the afternoon session.

  10. My alarm clock was set to PM instead of AM. I missed my early AM flight. Since then, I make sure to set the alarm on my iPhone

  11. I was sitting in the club lounge sipping coffee as my flight From Detroit to Newark took off without me, as I was positive Detroit was an hour behind us. Duh!

  12. The last day of my honeymoon coincided with the first day of daylight savings time. We went to check our bags, and was told that our flight left 10 minutes ago. That was before the days of smartphones, so we were oblivious. The next flight was completely full, but luckily someone else must have made the same mistake, so it was only another hour or so.

  13. Departed US thru UK and arrived in Lisbon late evening for a training that I was co-leading the next day, back in the days of Blackberrys. Made a few calls, sent some emails. Last thing I did was sync my Blackberry with my computer (when that was a thing!) and went to bed. Woke up to bright sunlight before my alarm, feeling ridiculously refreshed, bright sunshine. Blackberry said it was 4.30am. Went to the gym, got ready and still time to kill before my alarm went off at 6.30am. Went down for breakfast at 7am, started browsing the meal laid out for the team, and thought the options were very strange for breakfast: roasted vegetables, salads, chicken in white wine sauce etc. Chatted with the team. Then discovered it was actually lunch. Sync’ing the Blackberry had set the time back to US Eastern time. I was 5 hours late and missed the first half of the day!

  14. Showed up at DCA to check in for my flight…that was leaving from IAD. Also, lost count of the number of airline travel credits from canceled flights that I’ve let expire.

  15. The first day of daylight saving time fell on the last day of my honeymoon. When we went to check our luggage, we discovered that our flight had departed ten minutes prior. That was before to the existence of cellphones, so we were unaware of it.

  16. If you travel far and wide, especially with time zone changes, you make mistakes. With each mistake, you learn backup strategies to avoid the same mistakes, but make new ones on the way. That is the way with journeys…

    Always check the hotel alarm clock to make sure it isn’t set to a time you don’t want to wake…

  17. 1. Seriously underestimated the time it would take to get from the lounge to my connecting flight in a different terminal, and so missed it. The airline had no further flights to my destination that day. Amazingly, e airline booked on their competitor at no cost.

    2. I confused the departure time of connecting flight with that of the first flight, and so arrived way too late at the airport. I had buy a new last minute one-way flight, which cost a lot.

    3. I booked a room with a small enterprise for the wrong month. Upon arrival, they had no rooms open. They handed me over to another party which also had rooms in the building who was able to accommodate me.

  18. You mention an American Airlines DC-10, if it was after 1990, it was likely an MD-11. AA famously purchased a fleet of MD-11’s in 1990, largely for operating their service to Asia. The word on the street was that the purchase carried fuel burn and range guarantees, which AA apparently cashed-in on big time. The bulk of my AA miles was flown in Biz Class on that aircraft, which was horrible (non-lay-flat seats with sheepskins on them). AA sold the entire fleet to FedEx to carry freight after the MD-11 Accidents started piling up. I’m guessing nobody shed any tears over that one (excepting maybe the pilots qualified to fly it, and even then maybe not).


  20. TexasTJ,
    They were actual DC-10s. American flew them around 1990-1991 from Honolulu to Auckland and Sydney. The MD-11s never flew to the South Pacific.

  21. I was exhuasted and fell asleep in front of my gate and missed the flight by 10 minutes. Had to wait a significant amount of time to catch the next one. I had even set my phone alarm, which was going off, I just did not wake up.

  22. Used a 3rd party booking agent for an international domestic airline which didnt take US CC.

    Airline changed flight to one leaving before I landed. Immediately contacted both them and 3rd party. Airline said tough shit, 3rd party said, we can’t make them

    Canceled it, booked with more expensive airline that did take US CC and spent 4 months fighting first airline and 3rd party to get any money back.

    Ripped me off on cancellation refund but lost me as a customer forever and I’m there flying atleast once a year. And I make sure anyone thinking of booking them knows what scumbags they are.

    BATIK, I’m looking at YOU

  23. Did not read my JetBlue ticket and showed up at sfo instead of Oakland airport with my family.
    Missed the flight but JetBlue booked me on their next flight without penalty. That was around 2002.

  24. My stupid mistake: a Las Vegas departure booking on WN, I went back and forth debating should we go home on Tuesday/Wednesday/Tuesday? I thought I picked Tuesday as it’s always good to leave Las Vegas sooner than later. Upon trying to check in, I discovered we could not since our flight wasn’t til the following day. I’m pretty sure that extra day in Las Vegas cost plenty with my bonehead move!

  25. Freshman year college Spring Break. Went with dorm mate to the USVI. Backpacking. Mid-1970s. Party time and could buy any booze at age 18. In our home State purchase age was 21. An ancient DC-3(?) flight from Puerto Rico to St Thomas was one wild unexpected thing. On return home we connected in MIA. We both loaded up with maximum allowable amount of booze like Mount Gay rum, etc. purchased in St Thomas or St John. Dirt cheap compared to home. Figured we’d throw a big party for our dorm mates after getting back home. We (1) did not know we had to go thru Customs in MIA when coming from a U.S. territory. We (2) also didn’t know that the Federal “drinking age” was 21, regardless of the laws at our flight’s origination point. So Customs confiscated all of it because we were underage.

  26. Lost 50k sign up Avios bonus after min spend because fine print said my Avios account needed to be US-based for the Chase card. It was Canada based but was a simple matter of switching my address to the U.S. one.

  27. Meeting your traveling companion in a connecting city instead of originating together or taking a non stop on another carrier instead. Something happens 33% of the time. A delay , weather , tight connection , etc that causes added stress. One person link up and re position for the trip. 😉

    As much as I love American Airlines FAs I will report a grumpy FA for giving me an attitude when flying in business class. I don’t tolerate any of that. Report them. Chances are that’s how they treat their fellow co workers.

  28. Family of 5 flying MIA – BCN on Iberia. Two kids passports had 89 days left on them from our return date. Iberia agent in Miami wouldn’t let the two kids (15, 13) on the plane so we had rent a car to drive 3 hours back to Naples, get their birth certificates, rush through the single day passport process in Miami, and catch flights the next day. Iberia had only two open seats the next day so I had to use 300k AA miles to get them there. 300k AA miles, two hotel rooms for one night in Barcelona, lost day from trip, rental car for a day, passport expediting service, hotel room in Miami. All for one day short on the time left for the passport after our return date. Iberia supervisor sided with newbie employee and it cost me dearly. Closest I have ever come to being arrested in an airport. 5 years ago and I’m still mad about it.

  29. Showed up at LGA for a flight to St. Louis, but the flight was leaving from Newark. Luckily, it was a Saturday morning. I found a taxi driver who made it from LGA through Manhattan, and the Lincoln Tunnel, and I made it to my flight. The person checking me in in Newark did a wonderful job calming me down.

  30. In Ho Chi Minh City on March 15, 2020, I chose to enter, not knowing the last international flight out before the Covid lockdown would be the next morning at 9:00 a.m. Thankfully, I made it back to Singapore but, because of the quarantine, I had to sleep in Changi for 3 nights first.

  31. Just last night after sheparding my Emirates New First DXB – FRA I saw EK had swapped equipment I found GVA the next day which was making it tight into Munich for A380 First home to IAD, but still availablity!!! And EASY using EK online chat with real person
    My mistake was I simply forgot to also check Brussels ;-(
    But did this morning and found availability and again via Chat then phone to pay the additional $2.47 Beligum tax
    This was an award ticket Cleary the easiest fix for my eagerness

    Glad yours turned out well, too 🙂

  32. I had a bad experience at EWR’s FIS. I had flown Polaris class into EWR and waited for my “priority” bag to arrive. The Y bags were being delivered, and those customers would show up to the claim area – pick up their bags and head through customs. There were 10 of us still standing waiting – now :50 minutes after arrival. Finally our bags showed up on the claim carousel. We were all passengers with “priority” tags.

    When I got to the EWR Polaris Lounge, I started to write my “strongly worded” email! Fun fact…my laptop doesn’t change time zones automatically and after a bit of time – actually longer time. I pulled up my phone and it was :15 minutes before departure time. Threw everything into my bags and RAN to C84, yes the furthest gate away in terminal C. By the time I arrived, I was soaked – (sweat) and out of breath – (asthma). Got into my seat, and found my emergency inhaler, so I could breathe.

    EWR international arrivals still suck! And, I no longer travel with a laptop.

  33. @D3kingg. None of us want grumpy FA’s. That includes all classes on the flight & everyone should report that kind of behavior, regardless of their seat assignment. I only wish I could say that really happens. However, as long as my FA is not UNFRIENDLY, I lv that part alone

  34. I bet we’ve all learned this the hard way: Booked on a J or F ticket for a long haul.
    Better Half™ and I went to hang in the lounge and ate and drank and ate and drank before boarding and then…the airline attendant gave me the friendly stink eye that I couldn’t eat all my in-flight dinner and desserts. I was ashamed, but completely stuffed and had had enough booze.

    Lesson learned. And yet I still did it again at least two more times.

  35. Renting with Hertz. My latest rental was $171/wk, but, after several extensions, when I returned it, they hit me with $1400 for a month. Not looking forward to fighting this one.

  36. At the old MSY airport, went to the Delta terminal to catch a Delta flight. TSA agent mumbled something like, “Are you sure?”. Once past TSA, realized flight departed from an adjoining terminal. Went thru TSA a second time, and I was running to the furtherest gate, noted several others (including a deadheading FA) in hot pursuit. We arrived as the Gate Agent was closing the jet bridge door. Since there were so many of us crying like a bunch of little kids, she relented and let us onboard.
    Moral of the Story: Pay attention to the Departure Board!!

  37. At some point, the timezones will get you. My mother passed away while my then-bf was on a business trip in China. I raced to get him a ticket home, and neglected to take into consideration that while it was evening in the US, it was already the next day in Asia. Ended up booking a flight something like an hour before check-in closed. Fortunately, when I explained the situation, the rep was happy to rebook for the next flight without charge. USAirways sure had its quirks, but when push came to shove, they always pulled through for me.

  38. My first extended trip was by Greyhound at 17 and after 11th grade, going from a city near Buffalo, NY to Annapolis, MD for a six day summer introduction (Summer Seminar) to the Naval Academy. Being new traveling and traveling solo, I checked my suitcase through to the end stop. I went through a number of stations with my final ones being Washington, DC, Baltimore, MD and finally Annapolis, MD. When I got there I found that my luggage did not travel as fast as I did so I got to go to the Naval Academy without fresh clothes. It gets better. My checked bag finally arrived at the bus station three days after I did and I walked quite a distance to the station every day. That lesson was solid. If you want your luggage with you, you have to make sure it stays with you including seeing it loaded on the bus and collecting it whenever you change busses so you can see it loaded on to the new bus. I was mistrustful of airlines transferring luggage when I started flying but I have never had checked luggage lost or delayed.

  39. I love how many of us had near-misses and missed flights due to time zone screw up, airport mix up, booking on wrong date, and of course gate changes.

    Strangest experience for me was in HND or NRT years ago when they used to bus people out and you climbed stairs out in the tarmac.

    Arrived early but decided to make one stop to buy a camera at this shop far from the gate, thinking we can still make it to the gate about 25 minutes prior. It turned out the last bus to depart for the plane left 30 minutes prior to departure, and we could only stand there and watch the plane that was still preparing to fly with people climbing up the stairs.

    Stayed an extra night in Tokyo (probably one of the best places to be stuck) and flew out the next day.

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