How to get out of an airline pickle


Hey Reader,

The last time I was in Italy, I got a weird email the night before leaving. It told me to check in online to avoid delays, but then I got a separate email saying I couldn't check in online. The next morning, the airline just...couldn't find me or my reservation.

I was not in whatever system they had, and I never got to the bottom of what happened. Has this ever happened to you??

I bet you can imagine how this played out. The Italian airline told me to go to a different person to get help. That person told me to call Air France. And the Air France support line was closed until 10am, because it was the weekend, and it's France. And all of this was at...5:30am.

Needless to say, I missed my flight. My husband and I sat outside and watched the ocean for 5 hours while we waited for the Air France hotline to open for the day. We ended up flying to Paris almost 12 hours after the original flight left, getting a hotel, eating dinner at 1am, and asking our neighbors to take care of our pets, because our pet sitter couldn't stay another night.

Guess how much the airline paid us for all that? A big fat $0.

Now that I am a travel advisor, here is what I wish I knew back then. It would have helped us get out of that pickle so much easier.

  • Book your air through a travel advisor (like me) who offers a 24/7 air support desk. If we had done that, we would have had help when we needed it, instead of 5 hours later. You can call the air desk while standing in line at the airport, or while someone else calls the airline hotline. Always work multiple channels at the same time, if you can! On that note...
  • Travel with a cell phone that lets you use local cell service. We really struggled to make calls over WiFi at the airport, and it added to the stress. I now use Airalo's Discover Global Esim, which is more affordable than my phone carrier's international plan. It's easy to set up, and I can call whoever I need to, and stay on hold for hours. (They don't pay me, I have just been really happy with them.)
  • Don't skip travel insurance. Airlines make mistakes, even when you do everything right. If we had travel insurance, we could have gotten reimbursed for the ~$700 that we had to pay out of pocket because of this pickle. Here is the company I use and recommend. (They do pay me a small commission if you use this link.)
  • The more documentation, the better. This is especially true if you are flying into/out of the EU, since they have laws that entitle you to reimbursement for delays. (And yes, of course the airline denied our claim - yet another reason we should have had travel insurance.) Anytime an airline screws up, try to get something in writing if you can. You can also take notes on calls with airlines, and include the names of people you spoke to.

I hope these tips help, Reader. Our current government shutdown in the US is affecting TSA and air traffic controllers, and Thanksgiving is the busiest time to fly. There are inevitably going to be a lot of delays and cancellations this fall. Even if you already have airfare booked, it's not too late to get travel insurance!

Please don't be me and sit at an airport for 5 hours - they don't all have sunny weather and sea views :)

-Carolyn

Windward Path - Luxury Travel Advisor

Hi, I'm Carolyn! I believe your vacation should actually feel like one - not another project to manage. As a luxury travel advisor based in Seattle, WA, I'm here to ensure every journey delivers exactly what you desired, completely effortlessly. Think of me as your personal curator, your cultural interpreter, and your detail-obsessed advocate, all in one. I email weekly to the Windward Circle, a group of thoughtful explorers who receive insider insights and cultural travel inspiration. Join us!

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