Sometimes, when you plan a trip, everything just works. Things go easily. Schedules hold. Bags arrive. Flights are smooth. And everyone is happy. But, there are other times when the opposite is true, and almost nothing goes according to plan, and that means that finally arriving at your destination is a greater reward than expected.

Interestingly, one of the previous posts here is about a chaotic travel day, so I certainly don’t want o give the impression that these things are completely self-inflicted. However, as a general rule, we do take chances with travel, recognizing that the journey and experience is half the fun. But this trip got off to a bonkers start which all worked out in the end based on a few frequent traveler moves which would have otherwise sunk us.

We have been planning a trip to Maui with some of our closest friends for a number of months. During that time a lot of effort was placed on making sure we picked the right flights to accommodate vacation and work schedules, commitments of the kids, etc. We finally rested on a trip just short of 14 days, beginning the end of June and running into the second week of July. Fortunately we didn’t have to worry about lodging, as we already had that taken care of with a pair of two bed two bath condos in Kihei along the southern Maui coast, so it was primarily going to come down to airfare.

Anyone who has traveled in the mostly-post-COVID world knows that air travel is full of its normal quirks plus unique new challenges. I’m not talking about masks, at this point no one should care; if you want to travel, just put it on, wear it right, and get used to it. What I am talking about is the new unpredictability of flights and airlines. It has forever been a balancing act to buy a flight in advance without expecting there to be some amount of nominal changes in the schedules. That isn’t a big deal, and most veteran travelers expect it and handle it in stride. However, COVID has changed labor pools, allowed increased flexibility with tickets, and a number of other things to ensure customers remain interested in travel which have resulted in a massive increase in the degree of difficulty of planning. This has destablized the entire system.

For this trip to Maui, on our schedule we did something we would normally never do, splitting a trip across two different air carriers. Full disclosure, I am a top tier frequent flier (Executive Platinum) on American Airlines, and have been for a number of years. I know a lot of people dislike them, but I couldn’t be happier. The customer service I receive is way above and beyond, the perks are significant, and they have become a great enabler for both business and pleasure travel. But this time, it made sense to split and not fly American round trip from Las Vegas to Maui. The decision was to buy Hawaiian Airlines to Maui on a direct flight, and then a return trip on American using the standard redeye back.

This was mistake number one. Honestly, Hawaiian Airlines has been a great experience in the past, and the new direct route was really appealing, but COVID really damaged their business. Many people I know have had flights moved, cancelled, rescheduled, with only very matter of fact communication. We got to experience that firsthand when an email arrived cancelling our direct flight, and placing us on a new flight, with very different departure times and an extended layover in Honolulu. That’s the worst. Unless going to Oahu, we avoid Honolulu altogether. The airport is dated with very few options for food, and an extended layover is punishment. We decided to cancel the tickets, collect the refund and purchase other tickets.

Enter mistake number two. We had the opportunity to purchase outbound flights on American. The price was reasonable for us, but for our friends who had to pay for checked bags and had one additional person, it was less of a bargain so we agreed to purchase tickets with them on Southwest. One more sidenote here: Southwest is a fake major airline, and not a group I choose to fly with often. I have a long list of reasons that won’t provide here, but I will go out of my way to not patronize them. Nevertheless, we bought tickets leaving on Saturday morning which would get us in at 3pm local time Saturday afternoon, allowing time to grab groceries, unpack, and maybe squeeze in a swim before dinner, a drink, and an early jet lagged bedtime.

Finally, in preparation for the trip, my family of four needed to get COVID tested to clear the Hawaii Safe Travel program. I understand the goal of the program, and having used it a few times now, it is manageable. Does it really make a difference and minimize the spread of the disease? Maybe initially, but that’s likely behind us now. And being fully vaccinated – primarily to make travel easier – someone will someday have to explain to me why Hawaii accepts people vaccinated in Hawaii without testing but not people vaccinated outside Hawaii. Perhaps Moderna sent Hawaii a better version of the vaccine than Nevada received *wink* *wink*. Due to our schedules, my wife and I had to split up testing, so she and our oldest were tested early on Wednesday afternoon while the younger and I got tested early on Thursday afternoon. The big thing to remember here is that the testing has to be completed within 72 hours of your departure on your last leg leaving the mainland entering Hawaii. For a late morning flight to the island, we would definitely be safe. We thought. Until Southwest happened.

If you’ve been watching the news the past few weeks you caught that there were a series of computer glitches and Southwest cancelled a ton of flights. But that subsided. Until the past couple days, when, according to a few Southwest employees they saw a rash of cancellations unlike anything they’ve ever seen before.

That’s enough backstory, so I’m going to pick this up with Friday morning, the day before our Saturday departure. I’m going to leave out most of what happened to our friends, because their story is even more insane than ours and would be way too much to type.

Friday morning my wife received a text from her friend saying that Southwest had changed their Saturday flights due to weather. I immediately found this funny because no one can accurately predict weather 36 hours out unless we are talking major storm, and there was nothing like that on the radar. But no worries, Southwest had rebooked them on flights days later which didn’t actually match up to get them from New England to Hawaii. It was pretty incredible. When that happened, I immediately started looking for “backup tickets” on American that weren’t going to require a mortgage. I don’t know exactly why, but I just had a feeling that this was going to be the beginning of a nightmare, and I didn’t want to get stuck at home, not able to make the trip, with a bunch of credit on Southwest that I would never want to use. I found ticket options on American for the next day which would get us from Vegas to Hawaii, for about $240 each. Seemed pretty reasonable, but this started the problem.

Last minute flight purchases should never be done hastily. Weird routings, connection times, etc., need to be carefully evaluated to make sure everything works. And that became a big concern. Because of the change in flight schedules, and that we would no longer be departing the continental until late afternoon or early evening, we had two people who would likely have COVID test results outside the required 72 hour timeframe. Everyone who goes to the islands has heard horror stories of people getting turned around for minor issues with their paperwork and I didn’t want to chance it. Since the local labs wouldn’t be open in time before we started traveling, I booked tickets on American with the following routing, all times local:

• Leave Vegas @ 10:50 am
• Arrive PHX @ 12:00 pm
• Leave PHX @ 3:30 pm
• Arrive LAX @ 5:00 pm
• Leave LAX @ 6:00 pm
• Arrive Maui @ 8:45 pm

And here’s why: Phoenix is one of the few west coast airports which offers a rapid COVID test which is accepted by the Hawaii Safe Travels program. So the plan was to get to Phoenix, get them out through security and tested, back through security, and on to LA and then Maui, while hoping that the results uploaded to Hawaii in time to make sure they could stay on the islands and not get sent home. I know, kinda risky, but since their existing negative tests would have expired we would potentially need a back up.

But, the good news was that this was just a contingency, there is no chance we would take that ridiculous routing, and pay too much for repeat tests to satisfy a broken system. I was sure we would just end using these tickets as credit on our next trip. The mere act of buying the tickets, and making the testing appointments was enough to guarantee they wouldn’t be needed. Additionally, my wife thought this was unnecessary which was further assurance that it was overkill, no way could I be this right.

Until Southwest asked me to hold their beer.

Saturday morning we got up to head to the airport for our 9:00 am flight to LA and 11:00 am flight to Maui. However, a text message had arrived around 5:00 am rescheduling us through San Jose on a flight departing after the COVID tests would expire. So here comes the decision: would the Hawaii screening people notice the testing time being a few hours too early? Would that be worth the very expensive gamble of a return flight, new test, and flight back to the islands? Or should we just go with the contingency plan already in place? We went with the contingency plan and cancelled our Southwest flight, headed to the airport a little later to board our new, albeit geographically inefficient routing on American.

Look, I’m okay with reschedules, but not at the absolute last minute when there are logistical elements in place which can’t be changed. And then blaming it on weather – which was utter crap because no one else changed flights in those areas.

Check in through the American Priority desk, easy. Get to the gate with snacks. Easy boarding and arrival in Phoenix. Then, we had to get two of us outside security for a test which we thought was the right test and would produce results quickly enough to be useful. Fortunately it was and they did. BUT, while the testing was taking place, our next flight, the one to LA, was delayed. Just 30 minutes. That meant we would still have 30 minutes to make our connection and we knew the gates were adjacent. That was plenty of time.

Or so we thought until the dreaded pop up in the American app came up telling me to rebook my flights to Sunday because we would miss our connection in LA. That’s when it got real. And it’s also not how we roll. We had looked through all the routes, checked for hotels in PHX to spend the night to resume our trip in the morning with teeth freshly brushed using complimentary hotel toothbrushes. But then we looked at hotels around LAX. While fewer choices, and significantly more expensive, we decided that we’d rather chance the trip to LA and potentially making the connection to Maui rather than calling it an early day and sitting in a hotel room in Phoenix to wait for a flight to LA in the morning. The best part is that the kids agreed with the risk taking decision, a solid vote for our parenting skills, so we headed to our gate while ignoring American’s request for us to pick new flights.

The other thing we had going for us, which I had failed to mention, was our complimentary upgrades to First Class on this one leg, so we were all sitting in the front of the plane, ready to make a speedy exit.

But, it was delayed again. And then started to board late. But the worst part, and this is a total “First World Problem” worst part, was being in First Class. You get the chance to board first, that’s nice. You get comfortable, maybe you’re served a drink. But then, you sit and watch while every other passenger boards the plane. In this case we were on an Airbus A321neo, which is a great aircraft. According to the specifications on Seat Guru, it holds 20 people in First Class, and 176 in the Main Cabin. I know the flight was full because they announced it, but what I don’t understand is why it felt like they had a rear door open and were just marching people through like the old circus Clown Car trick. I would have bet 500 people boarded that aircraft for the time it took. Finally we pushed back and the clock watching began.

We did learn during the course of the flight that there were a few other people on the flight in the same predicament trying to make it to Maui with our same connection. And that sounded like hope for us, but awful for them having endured multiple flights starting from Philly only to endure this same torment. It was decided inflight that our youngest, and the husband of another family, decided to run to the next gate and make some sort of scene to ensure that we made the flight. For those of you who know my youngest daughter, you know that not only is this something she would be perfectly willing to do, she would also be exceptionally at it. The girl has a gift, and is able to argue with anyone about nothing strictly for sport.

As we were about to land, the flight attendant made an announcement that there were a number of passengers on the flight trying to make a really tight connection to Maui and could the rest of the passengers please wait to stand. She then clarified with an update that the plane was being held temporarily but needed to make an immediate departure. They chose to run anyway. The moment the door opened the two runners bolted out of the plane and to the gate, with us following right behind. There were agents everywhere, they all knew our names, and were waiting for us. In reality it was a brilliant decision even if they weren’t waiting. For some reason, Hawaii requires that you show ID when boarding at the gate. Our 15 year old didn’t have that with her. Nor did she have parents. But she did have a ticket and was there in time. They were going to have a really hard time not slowing the door close with her right there.

We boarded. We sat. We departed late, but we didn’t care. We didn’t need the $350 hotel or the ridiculous wait at LAX security. We would arrive in Maui reasonably as predicted. The pilot made up time in the air, and was able to get us in on time. The crazy had paid off. Potentially.

We still had to clear the Hawaii Safe Travels checkpoint, and we still didn’t know if the tests from the Phoenix airport would be accepted. The webpage had already generated our QR codes for entry, but they may have been based on the old tests which had timed out. Further, when we uploaded the new tests, the system told us the testing partner wasn’t recognized, which was crazy since I had literally made the appointment using a link to the testing company on the Hawaii Safe Travels page. The good news is that we will never know, because everything worked. The codes scanned, we didn’t have to plead a case, and we walked to baggage claim knowing everything had gone in our favor.

Let’s be honest, for every story like this, there are several which end poorly. But the best advice I can give to any traveler to take a deep breath and realize that there is nothing you can do to control the situation, all you can do is adjust and accept. Anger and emotion at airline employees will only make things worse. A smile and a thank you can move mountains. These tireless employees get yelled at everyday, they are conditioned not to respond to bend. Despite what you think, you are not scarier than anyone else nor do you have any more power than any one else. You will separate yourself from the crowd best by being nice and calm. That is what will help you.

Beyond that, take the time to understand the business and how it works. There are webpages out there where you can look up historic on time flight performance, credibly search dozens of hotel booking sites at once, and learn airport terminal maps before you ever board your flight. All of those things were used this day to help us make the best decision. Finally, when it comes to air travel, loyalty still matters. A lot. I can’t underscore that enough. I favor an airline, you got me. But I can also tell you that between them and US Airways whom they acquired, I’ve logged over a million miles in the air with them, and they appreciate that and treat me accordingly. The kids are even Gold Members, and teetering on Platinum. If you are serious about travel, develop that loyalty with a carrier. Buy your tickets through their webpages and services, not third parties, because it benefits them and the fare class you purchase makes a difference for how they will help you when something goes wrong. If it is a difference of a few dollars, choose wisely.

In this case, everything worked out and we were able to arrive in one of the greatest places, to enjoy two weeks of relaxing and exploring with friends. It is such a privilege, how on Earth could anyone be mad about arriving slightly late?