Our Disastrous First Flight As A Family Of Four: I’m Still Mentally Recovering

I’d like to think that I’m a pretty competent air traveler — I certainly have the experience and knowledge to navigate just about any situation, since I’ve been a frequent flyer for around two decades, have logged many millions of miles, and study this stuff endlessly.

Ford and I are currently in Europe for an extended period of time, traveling with both of our sons, Miles and Jet, and other family. While we’ve traveled extensively with our older son, Miles, this is our first “real” major trip with our younger son, Jet, who is about to turn one year old (to me, there are just more downsides than upsides to traveling with super young kids, especially when they’re really easy kids at home, and you have loving family that’s also happy to stay with them).

I’d like to officially declare the outbound journey of our trip as the most stressful travel I’ve ever encountered. Of course this largely comes down to the pressure of wanting to do everything right for your family, plus the added complications of taking care of kids, traveling with five checked bags, etc. Everything is more high stakes when you travel as a family. If I had been traveling alone, I would’ve just said “screw it, we’ll try again tomorrow,” or something like that.

Anyway, in this post I’d like to talk about the first portion of the outbound journey. Sadly this isn’t even the only drama, as I’ll save the go arounds, diversion, and flight attendant falling to the ground for a separate post, as there’s a lot to cover. This is definitely one of those “when it rains, it pours” situations.

Before I even start, let me add one caveat — this is no way a complaint, as I accept full responsibility for what I booked, and the risks that entailed. If anything, this post is about giving credit to the amazing people along the way who helped us, and talking about the overall strategy of how to handle irregular operations.

A less than ideal routing from Miami to Skiathos

We’re kicking off our summer in Skiathos, Greece (JSI). That’s super easy to get to if you’re flying from Leeds (LBA) on Jet2 (and you can save up to £50 per person!), but a lot less easy to get to if you’re coming from Miami (MIA).

In the miles & points world, there are many of us who will book some itinerary in advance, and then try to optimize as the departure date approaches.

Basically, I had booked this ticket backwards — I booked a paid ticket for all of us to fly from Vienna (VIE) to Skiathos on Austrian, so I knew how we’d make the last segment of the trip work. The plan was to spend one night in Vienna, at the Moxy Vienna Airport, to leave a bit of a buffer.

A while back I locked in an itinerary from Miami to New York (JFK) in American first class, with a 4.5-hour layover, followed by an itinerary from New York to Paris (CDG) to Vienna in Air France business class. That was all booked on points, so was refundable up until departure.

My hope was to turn the Miami to New York to Paris to Vienna itinerary into a one-stop routing, ideally in a single ticket. In the past that would’ve been easy enough, but with how miles & points have evolved, unfortunately nothing better opened up… not even in economy! Obviously this itinerary entailed some risk, because if the Miami to New York flight had a serious delay or cancelation, I’d have to regroup, and find a better way to get to Vienna.

Again, I fully acknowledge we were taking some risk here, but my general thought was that we could have a delay of well over two hours on the first flight, and still make the connection, despite having to recheck bags.

Some might say “well you should’ve built in an extra buffer.” Yes, if the goal was to be as certain as possible that nothing goes wrong, that would’ve made sense. But when you’re traveling with five pieces of luggage and two little kids, the goal is also to have as few overnights along the way as possible. So it was a calculated risk, which I accept full responsibility for…

Things were looking good… until they weren’t

On the day of travel, everything was looking good initially for our Miami to New York flight. The inbound flight showed as arriving on-time, we went to check-in, we checked our bags, and we headed to the Admirals Club by gate D15. For that matter, just about all flights from Miami to New York had been operating on-time that day.

Within five minutes of arriving at the Admirals Club, I received a push notification through the American app that our flight was delayed by 30 minutes. Okay, no biggie, I thought. I appreciate American now shows the reason for delays… that’s progress!

I wasn’t too worried, initially. I checked inbound flights into JFK, and I saw there was some flow control, but it showed the situation as improving rather than getting worse, and on top of that, Flightradar24 showed few cancelations into New York. I figured if anything, it would just make our connection more pleasant, since we wouldn’t have to wait so long.

Minutes later, the flight was delayed by another 24 minutes. I tried to remain optimistic, but was now starting to get a little nervous.

Nothing calms my nerves quite like some Admirals Club vegetable minestrone (I kid!), so I helped myself to a bowl of that. As I started walking back to my seat, I got a push notification — the flight showed as canceled, and my heart started to sink.

Now, I won’t get into conspiracy theories as the reason for canceling a not full flight when other flights were operating on schedule (rather than just delaying it, if needed), but let’s just take that at face value.

UGH, talk about bad luck! What concerned me most about the cancelation wasn’t finding another way to get to Vienna, but instead, the fact that we had five checked bags on a flight that was now canceled, and American isn’t exactly known for great baggage handling!

Honestly, I should’ve known something like this would happen. Two years ago when we took Miles on his first long haul trip, we also faced major operational issues, which created a completely chaotic trip. I think we just have a curse when it comes to first kids trips, because everything has otherwise been smooth since then.

Karol in the Admirals Club was delightfully helpful

On the plus side, I was about two feet from the customer service counter in the D15 Admirals Club when the push notification came in, so stopped by with soup in hand, to try to get rebooked. That timing ended up being critical, since there was quickly a queue of a dozen people behind me, and the inventory on the next flight disappeared within minutes.

I was helped by Karol, and my gosh, she couldn’t have been lovelier. I often give American a hard time for its service culture because I know how good it can be, and how good it consistently used to be. Back in the day, Admirals Club agents were often referred to as “AAngels,” because they just offered such a high level of service. Karol is an absolute AAngel, and represents the best of American.

Within minutes, Karol rebooked our whole family on the next flight to New York (we were downgraded and spread out across the plane, but who cares?!). I explained to Karol the checked bag situation, plus the overall pickle I got myself into. While we of course had all the essentials in our carry-ons, we had checked car seats, and most of the clothes and other things our kids would need during the trip.

Karol was incredible. She said the bags should be rechecked automatically on the next flight. She explained that she didn’t want to manually retag them in a way that would increase the odds of them being lost, but she said she’d keep checking on them (the app wasn’t showing their status at this point). She encouraged me to check back with her frequently, which I did.

Long story short, one by one, the bags were automatically updated to correctly show as being tagged on the right flight. However, one bag didn’t seem to want to retag correctly.

It’s just so nice when you have Admirals Club agents who don’t make you feel like an inconvenience when you ask them for help. Like, it’s sad that this is remarkable, but it is. She was so lovely that she even told me when she was about to have a 15-minute break, and told me to check back with her afterwards. Heck, when I told her I’d go to the gate, she jotted down my phone number and told me she’d call me to let me know if the bags made it or not (and I feel like if they hadn’t, she would’ve helped me with making something work).

Eventually we boarded our flight to New York, which was at least on-time. This left us with a 1hr58min layover in New York, where we’d need to claim our bags, and then check them in again.

Once at my seat, the American app finally showed proper baggage tracking, suggesting all bags had been loaded onto the plane.

As promised, Karol even called me, and left me a voicemail, to let me know all our bags had made it onto the flight (we were taxiing at this point, so I couldn’t answer).

The kindness and professionalism Karol showed really stuck with me, and now I know where I’m going for customer service in the future when at MIA.

Things were looking absolutely amazing… until…

I knew things would be a little tight, but I figured if everything went as planned, we’d be fine. Sure enough, our flight left on-time. We were scattered all over the plane and downgraded, with the kids split up, but at least we were on our way.

We departed on-time, and landed more or less on-time. Hey, this is probably really going to work out, I can’t believe it! We arrived a little after 9:30PM, and headed down to baggage claim. While the bags took a little longer than I would’ve liked, one by one, they made it. Well, at least the first four did. The last bag showed as being “unloaded from plane in JFK,” but not as having “arrived at baggage claim in JFK.”

The bag had allegedly been unloaded at 9:47PM, the same time the other bags were unloaded. However, over 10 minutes after the other bags arrived, the baggage belt stopped, and there was no sign of the last bag. WHAT ON EARTH?!?! Go figure this was also the bag that had most of Miles’ clothes in it, which is probably also the most important bag for the purposes of this trip.

This is where the most stress of the journey started

At this point, the situation almost started to feel comical. Should we all just run to make our Air France flight, and abandon our last bag? I knew if we did, there’s no way we’d actually see it in Europe this trip, especially since this ticket was just from Miami to New York. Or should we just not take the Air France flight and regroup? Then we’d almost certainly forfeit our paid flight from Vienna to Skiathos two days later, which would also kind of suck.

I had to make a quick decision. I have to be honest — at this point I had lost hope in my head, and just had such a depressed feeling about the whole situation. Still, I knew the clock was ticking, and I had to put in my best effort. So I sent the whole family to Air France’s Terminal 1, and told them to hurry to check-in.

The missing bag was carry-on sized (though had liquids), and I figured worst case scenario, I could just board directly with that.

American has a baggage office at JFK, and it had a queue that was probably a dozen people long, with one person working. I would never cut a line, so I figured I’d have to try something else. There’s also a little podium by baggage claim, with a couple of employees. To put it politely, I haven’t generally found the American baggage agents at JFK to be folks who go above and beyond.

Out of breath and with my heart beating fast, I explained the situation to one of the employees. He looked it up, and he could of figure out what happened. Basically, while the bag had been placed on the rebooked flight, the tag wasn’t updated correctly, so it probably never made it to the carousel. He explained it was probably in the back room, and just needed to be scanned correctly, so it could be released.

“Thank you so much! Is there any chance you could help me with that?”
“You have to go to the baggage office.”

I kept asking politely, but he said nothing else could be done, and that he couldn’t do anything. I started running over to the baggage office, and along the way, I ran into an American employee with a walkie-talkie. Probably talking at about 500 words per minute, I explained to him what happened. I think he could sense my desperation.

“Please, please, please, is there any chance you could just radio to someone in the back room about this bag tag number, and see if they can bring it out? I know this isn’t your fault or your job, but you’d literally save our vacation, and you don’t know how much of an impact it would have.”

“I can try,” he said. He radioed his supervisor with the bag tag number. “Thank you so much, you don’t know how much I appreciate you.” He was then getting ready to walk off, and I said “please, could you just stay with me for one more minute? I’m so sorry, I owe you more than I can put into words.”

Well, two minutes later, guess what was brought out of the back room? THE BAG!!! Honestly, I couldn’t believe I had pulled that off. I quickly asked if I could take a picture of his name tag so I could write a note of gratitude for what he did, and while I’ll include his full name in an email to American, I want to express my appreciation to T. MERXXXX (he only had his first initial, and those are the first three letters of his last name). I sprinted over to Terminal 1, and I couldn’t believe we’d have a happy ending!

Air France was flawless as usual, but that wasn’t the end of the drama on the outbound portion of this trip.

Bottom line

Suffice it to say that our first long haul trip as a family of four didn’t exactly go smoothly. We had a flight delay, then a flight cancelation, and then one of our bags randomly ended up in some back room at JFK, with little time to spare.

This was honestly the most stressful flying experience I’ve had, primarily because of how high stakes it was due to the family aspect. But really my takeaway is the people along the way who saved the day, and went above and beyond. Karol in the Miami Admirals Club, and T.M. in the JFK American baggage claim area, you two saved the day.

Like I said, I feel like there’s some sort of a curse here, because this was only the start of the drama on the outbound portion of our trip.