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Stranded in Paradise: How the 737 MAX Grounding Left Us Stuck in Hawaii

Our holiday plans took a sudden turn when we found out our return flight home was canceled. With no other options in sight, we're left pondering our next move

by Alesandra Dubin

January 9, 2024

Working poolside / Photo: Courtesy of Alesandra Dubin

As a travel writer, many of my trips fall into the category of bleisure: research for story ideas combined with plenty of personal pleasures, often with my family in tow. This week, such travel took the form of a first-time visit to Lānaʻi, the luxurious Hawaiian island owned by Larry Ellison and populated by The Four Seasons Resort Lānaʻi and Sensei, a Four Seasons Resort.

It was our family’s last hurrah before the kids headed back to school, and my husband and I properly settled into work after the slower holiday weeks. We were wrapping up several days of horseback riding, archery, stargazing, and pool time at the impeccable beachfront Four Seasons Resort Lānaʻi.

The writer horseback riding in Hawaii with her family / Photo: Courtesy of Alesandra Dubin

The first sign of trouble in paradise materialized in the early morning of Saturday, January 6, when I was up with jet lag scanning my phone and came across a breaking news headline: Alaska Airlines grounds fleet of Boeing 737 MAX 9 jets after midair ‘incident’.

We were scheduled to fly home on this aircraft the following day, having selected the flight with intention. We reasoned it would be a new aircraft with what passes for creature comforts even in the coach cabin. Of course, the main priority for all travelers is to get to their destination safely, so I’m grateful for the essential, if massively disruptive, grounding during the investigation.

Photo: Courtesy of Alaska Airlines

In what would reveal itself to be a strategic blunder, we waited until the airline officially canceled our flight, which it inevitably did. The email notification offered no viable alternative for getting home: “We tried to rebook you onto another flight, and we are currently unable to find you a new flight in the next couple of days from your original airport, or surrounding airports, due to limited availability.”

It offered the option to view alternative flights and rebook (having already established there were no flights), place the value of the ticket in a Mileage Plan Wallet for future use, request a refund, or call customer service to discuss.

The writer’s family at Nobu Lānaʻi / Photo: Courtesy of Alesandra Dubin

We spent what was supposed to be our final evening’s special dinner at Nobu Lānaʻi peering into our phones, searching for flights—and the landscape was barren. By then, all the 737 Max 9 flights to the mainland had been canceled, and all the displaced passengers had quickly filled every available seat on other aircraft.

We searched every permutation—every airline, every cabin, a wide range of inconvenient cities and several stops, skip lag options… and nada. It started to sink in: We were just plain stuck. But we were stuck in paradise.

The Four Seasons Lānaʻi graciously offered to extend a media rate as a professional courtesy for my family to stay until we got flights sorted. But a new wrinkle quickly emerged: A storm was coming into the area, set to last several days, and the ferry on which we’d arrived from Maui would not run in bad weather.

So we called another audible: We’d leave Lānaʻi on the last ferry ahead of the weather conditions and return to Maui while we still had the chance. In Maui, we’d also be positioned to get to OGG quickly should a flight home materialize with little notice.

Stranded in paradise / Photo: Courtesy of Alesandra Dubin

Here’s where being a professional travel writer comes in handy: I contacted a longtime contact at the Four Seasons Maui at Wailea (also known as the dreamy filming location of the first season of The White Lotus). The resort welcomed us as the least pitiable stranded travelers in history, setting us up with a suite on the elite club floor where my kids could help themselves to endless snacks in the lounge while my husband and I chipped away at work on our laptops from an unexpected remote outpost.

And that’s where I remain as of this writing: banging away on my laptop from a pool cabana, with breeching whales in view, while my husband chats to his Los Angeles office about payroll matters.

We still don’t have a return flight—or any meaningful updates from Alaska Airlines. We could very well be looking at several more days stranded in paradise.