Why I was denied boarding to Chile — and spent Christmas in Jamaica instead

Four days trekking through Patagonia. Two days exploring the streets of Santiago. One epic trip to Chile over the holidays and into the new year. I had it all planned out.

Unfortunately, as with so many trips during the COVID-19 era, my South American vacation didn't pan out as expected.

While summer (from December to March) is traditionally its high season for tourism, Chile didn't drop its five-day quarantine requirement for fully vaccinated travelers until Nov. 1, 2021. It seemed that was cutting it too close for most would-be tourists because I found incredible flight and hotel deals for a trip over Christmas. Having secured my travel bookings, I set about getting my paperwork and testing in order so I could visit the country over Christmas without a lengthy quarantine requirement.

Better yet, I expected to meet up with my colleague, Chris Dong, in Chile, as he was flying American Airlines to help him achieve another year of Executive Platinum status.

The plan was pretty much perfect. Maybe too good to be true. Because surely nothing is this easy when it comes to international travel during the pandemic, right?

Here's why I was denied boarding on my flight to Chile — and how I ended up spending Christmas in Jamaica instead.

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Chile entry requirements

Pre-pandemic, my biggest stressor on a trip to Chile would have been deciding whether I'd rather spend my afternoon rafting or hiking.

But we all know that travel during the ongoing coronavirus pandemic can be much more complicated than that. Visiting Chile, specifically, I had to amass a mountain of documents and details in order to even attempt to enter the country.

To be honest, I was daunted by the laundry list of items that Chile required for travelers. I had to undertake the following steps:

• Submit proof of vaccination to obtain a Mobility Pass issued by the Chilean Ministry of Health — which can take a minimum of four weeks.
• Provide proof of a negative COVID-19 PCR or serology test within 72 hours of boarding a departing flight.
• Complete a Traveler's Affidavit within 48 hours of boarding a departing flight.
• Purchase travel health insurance that provides coverage for COVID-19 and related health issues with coverage of at least $30,000.
• Take another COVID-19 test upon arrival and quarantine in a declared address in Santiago until the results came back (usually within eight to 10 hours).
• Fill out a daily health questionnaire regarding COVID-19 symptoms.

Now, you may have read the above list and thought to yourself, "That's way too much just to travel internationally right now."

And maybe you're right.

While many destinations now require proof of vaccination and a prearrival negative COVID-19 test result, Chile added a few more hoops to jump through, including a Mobility Pass that would be the key to skipping quarantine and being able to travel throughout the country.

Admittedly, I was ambitious. But it also helped that several of my TPG colleagues and one of my closest friends had recently visited Chile and said that, despite the backlog in the Mobility Pass processing, it took around two to three weeks for it to finally arrive in their emails and everything else had gone off without a hitch. I hoped the same would be true in my case.

There was barely more than a month left before our trip, potentially cutting it too close to get our passes in time. We kept our fingers crossed as we submitted our documents, including pictures of our passports, vaccine cards and declared addresses in Chile.

I received an email just a few days later that my vaccine was verified and was issued a Mobility Pass with a QR code a week later. Things were going much more smoothly than I had anticipated — or so I thought.

Related: When will international travel return? A country-by-country guide to coronavirus recovery

Departure denied

Before I knew it, Christmas Eve had arrived and it was finally travel day!

Over the weeks leading up to it, I'd had my doubts about whether this trip would actually happen, especially with the omicron variant spreading around New York City. But, with negative test results in hand and all my other documents printed and neatly sorted in a folder, I was eager to visit South America for the first time and in style — in business class on LATAM's 787-8.

As I rode the AirTrain into New York-JFK, I daydreamed about the tapas and cocktails I would soon be enjoying at the Virgin Atlantic Clubhouse (your LATAM business-class ticket gets you into both the Virgin lounge as well as the Delta Sky Club). I had allotted plenty of time to get to the airport since not only would JFK be busy on Christmas Eve, but isn't visiting the airport lounge half the fun, anyway?

I'm glad I showed up early. Terminal 4 was more crowded than I've seen it in a long time and there were at least 40 to 50 people waiting to check in for LATAM.

Fortunately, I could skip the economy line since my business-class ticket gave me Premium Access. In comparison, there were fewer than five travelers waiting ahead of me in line.

While I was waiting, a LATAM agent began to verify my documents. I then heard the words that you never want to hear from an airline employee: "Ma'am, your Mobility Pass is incomplete. I cannot issue you your boarding pass. You will need to visit the help desk to rebook your flight."

How could my Mobility Pass be incomplete if I had the official document from the Chilean Ministry of health in my hand?

I then learned that, despite having two doses of the Pfizer vaccine during my initial round of shots plus a third as a booster, only one of my doses had been registered by the Chilean government. I showed the airline agent my physical CDC vaccination card with all three doses noted plus my negative PCR test results, but they weren't enough to supplement proof that I was indeed fully vaccinated and boosted.

The LATAM agent made it very clear that I wasn't going to be allowed to board my flight without the verification of my second dose in my Mobility Pass, which could take days or even weeks.

I started to panic. At the very least, I was hoping to find someone else to talk to, perhaps another agent who could offer me a better solution or advice on whom to contact from the Chilean government.

Fortunately, I was able to flag down a LATAM manager who looked at my paperwork and pointed out the same error. There was no second dose listed on my Mobility Pass, and my CDC vaccination card isn't an approved document according to the Chilean government, thus she could not issue my boarding pass.

As a last attempt, she gave me the Chilean embassy's phone number, but nobody picked up, as it was Christmas Eve.

The manager told me that other travelers were running into similar issues with verification, but it was simply an administrative glitch or an issue in the system that wasn't in the hands of either the passenger or the airline.

Ultimately, there was nothing I could do — and I saw my plans crumble in a matter of minutes. Luckily, I was able to cancel my hotel reservations without a penalty, and I now have a flight credit to use on LATAM for future travel, so perhaps I'll eventually end up in Chile once the health department works out its Mobility Pass glitches.

If you plan on visiting Chile sometime this year, my advice would be to get started with obtaining your Mobility Pass paperwork as soon as possible — and give yourself ideally two months for full approval. Make sure that all the required doses of your vaccine are accepted and registered by the government. If you don't see them on your Mobility Pass, submit another validation request and wait for approval.

The official Travel to Chile website states, "If your vaccine validation hasn't come through, or you've has problems during the process, send an email in your native language with a simple translation into Spanish to this email address: ayudaregistrovacunas@minsal.cl."

Therefore, I'd recommend reaching out as soon as you notice an issue with your Mobility Pass. But as a fair warning, I still have yet to hear back to my own request — and it's been well over three weeks.

Scrambling to find new plans

Interestingly enough, Chris experienced the same issue with his Mobility Pass. Only one of his vaccine doses was approved by the government, yet American Airlines agents cleared his documents at the airport — perhaps they weren't scrutinizing his pass as diligently as LATAM agents were.

However, he ran into issues when he arrived in Santiago and immigration officials there noticed his Mobility Pass only listed a single vaccine dose. Luckily, he had submitted a correction request so that both doses of his vaccine were eventually listed and he was able to travel around the country, though there were still quarantine rule snafus.

To say that I was disappointed would be an understatement. But, life happens, and all sorts of travel mishaps can occur during these uncertain times.

Dejected, I headed back home from the airport to Manhattan, all alone on Christmas Eve. But I wasn't going to let this ruin my holiday week.

I already had proof of a negative COVID-19 test result taken that day, so I had plenty of options of where to go — especially with three major airports in my backyard.

I wanted something simple, as I didn't have the time (or energy) to go back to the drawing board. Fortunately, there are plenty of easy, nonstop flights to the Caribbean you can take from New York, and traveling somewhere warm sounded more than ideal.

As you know, you typically won't find a bargain if you're booking a last-minute flight. But my points and miles saved the day. I used the Google Flights "Explore" feature to compare fares throughout the Caribbean, eventually settling on Jamaica. I had JetBlue TrueBlue points to spare, and my flight cost about 12,000 points round-trip, which seemed like a bargain to me.

Of course, I didn't want to find myself in a similar situation where I'd be denied boarding due to not having the right paperwork. The Visit Jamaica website was easy to navigate, and all I needed was a negative COVID-19 test taken within three days of arrival and to fill out a travel authorization form. Done.

Even better, I found last-minute award availability for the Hyatt Zilara Rose Hall, an all-inclusive property for just 25,000 World of Hyatt points per night. I quickly transferred Ultimate Rewards points to top off my Hyatt balance, and my last-minute vacation was booked in a matter of minutes.

Related: Reopening guide to Jamaica for tourists

My colleague, Benji Stawski, had stayed at this property last summer, and he wrote a glowing review about the quality of the food and the breadth of activities available to guests. Upon reading his review, I was sold.

When you think of all-inclusive resorts, you may think of crowded buffets and rowdy spring breakers, but I found quite the opposite at the Hyatt Zilara. It was an adults-only property and it was surprisingly quiet over the holidays. While I prefer the beach over the pool, the Hyatt Zilara's infinity pool was stunning and even had a swim-up bar where it was fun to order drinks.

Beachside, I took full advantage of setting sail on a catamaran and kayaking, all of which were available to guests for free.

The meals were also delicious. My favorite restaurant was called "Fuzionz" and offered wok-style dishes, à la carte sushi, fresh fish and fantastic saketinis.

After all the planning that had gone into (and come to naught with) my Chile trip, the ability to simply show up at a resort and have all of the meals and activities taken care of was exactly what I needed. It was one of the most relaxing vacations I've had in a while.

Bottom line

Lots of things can go wrong with travel right now, whether your flight is delayed or canceled or you test positive for COVID-19 while abroad.

Here are the lessons that I learned from my experience trying to travel to Chile:

1. If you're planning a trip to Chile in 2022, submit your documents for verification as soon as possible and make sure all of your information looks accurate on your pass. Ideally, give yourself at least two months to work through any potential clerical errors you may encounter.
2. International travel isn't always this complicated right now. There are many destinations where it's relatively easy for travelers to provide proof of vaccination and negative test results — Jamaica, for example.
3. I can also now see why all-inclusive resorts have skyrocketed in popularity throughout the pandemic. It's hard to plan a vacation when you're unsure if restaurants or activities will be available due to constantly changing conditions and restrictions, so it's nice to have everything you need in a bubble. My resort even offered free COVID-19 testing for return to the U.S., so virtually all of the travel planning was taken out of my hands. I also felt safe in Jamaica as masks were required for both employees and guests all throughout the property, and there was a nurse on-site if you needed medical assistance at any hour of the day.

To this day, my Chilean Mobility Pass is still incomplete, despite resubmitting my vaccination card to get my second dose approved by the Chilean Ministry of Health, much like Chris was able to do. I'm not sure what else I'm missing at this time, but I might try again this year to see if the country has smoothed out its approval process.