Travel in the COVID-era

Last week, I posted an overview of our trip to Jamaica. This week, I’m diving into more of the details regarding traveling during the COVID-19 pandemic. Next up will be our experiences with Jamaica and the people overall.

Our life in COVID could be described as cautiously waiting. We’ve done things as they’ve become available and marked as “safe.” Some of them are filled with “what were we thinking?” in the following weeks. But, we’ve both been eager to take to the skies again and continue our explorations of this amazing planet.

What have we done during COVID?

We’ve also dined outdoors, stayed-at-home for weeks/months on end, quarantined, ordered endless amounts of takeout, and watched more old movies and television than I ever imagined possible.

Noah was nearing the end of his election period for PayPal sabbatical – 1 month of paid leave. We knew that our original plans of traveling the world in 40 days was not going to be possible still in 2021. So, we elected to do a standard week-long trip. But, to where?

We were both hoping to travel internationally, but Europe and Africa seemed incredibly difficult to plan… Not to mention the fact that the regulations are changing on a daily basis.

Asia was also unknown regarding reopening and regulations.

Maybe it would be best to stay closer to home? We settled on the Caribbean, and I opted for Jamaica.

Planning Travel in 2021

We had been watching our Instagram feed fill with people and their global treks. We’d spoken with colleagues who had come back this summer from India, Costa Rica, The Dominican Republic, Italy, Greece, Croatia, England, Colombia, and Spain.

We asked them, “But, was it difficult? Were you scared?”

“No!” We’d heard back dozens of times. “It was fine! They try to scare you out of traveling, but there were no problems.”

What had we been waiting on? Were we the last to attempt travel in these unsettling times? Had I lost my edge and fearlessness?

Were we scared?

Of travel…no.

Of not being able to get home…absolutely.

Jamaica required an entry approval letter based on a series of questions asked in their online travel portal. You have to answer basic questions about your health, your lifestyle, and your plans in Jamaica. They then supply you with a healthy dose of anxiety as they tell you that if you are found outside of the safety corridors, you will be fined and imprisoned. Cool!

You also have to show a negative COVID test within 72 hours of your flight.

We live in New York, so, we had to wait in some lines, but the Antigen tests are quick, and we can get the results in 15 minutes. No problem.

So, we had everything we needed to get into Jamaica:

  • Passport
  • Negative COVID test
  • Signed Jamaica Travel Authorization Letter
    • One of the passengers on our plane did not “sign” their letter before lining up at the gate. They were not allowed to board. They had the paperwork…But, they hadn’t followed EACH rule. No go. Remember getting credit for writing your name at the top of your homework assignments? It was preparing you for this day.

Upon our arrival in Jamaica, everything was seamless. Customs were a breeze. “No problem, Mon!”

Being Overseas in 2021

One thing that I’ve noticed is that even state-to-state (or city-to-city) is handling COVID a little differently. When you look at the world nations overall, each place has a very distinct stance on the pandemic and their plans.

Jamaica’s prime minister gave a speech on the day we arrived. He announced three upcoming “No Movement Days” based on the rising numbers of the Delta variant within the country. Everyone had three days to prepare.

Considering that we had lived through California’s “Shelter-in-Place” and New York City’s shut-down, we were familiar with the concept. We figured there would probably be a run on toilet paper and gasoline -right? Because that’s how everyone does it, right? We would be FINE! We wouldn’t need to take care of our cars and the hotel would have everything we would truly need. To save some money from the expensive hotel dining and mini bar, we elected to buy some cheese and crackers, a couple of cases of Red Stripe, several large bottles of water, some chips and cookies.

We also needed cash for upcoming excursions – we only had two days to explore. We had to make the most of it, and everywhere seemed suddenly to be “cash only.” Why? I wondered…

A Run on the Banks

We had gone into Negril to pick up a few supplies. We had planned to simply stop at an ATM in town to grab the necessary cash for our excursions. We stopped at one that had no line and promised to offer both Jamaican and American dollars. We tried it a couple of times, but it kept giving error messages. People started banging on the door – clearly we’d taken too long.

Oh, well. We can try a different one.

We went across the street to ScotiaBank. It had a line of 12 people – odd… But, this is a different country. We waited in line.

Machine error.

We went to the Jamaican National Bank down the road – another long line.

Machine error.

Weird we thought. “Maybe we’ll try some others in the morning.”

We thought maybe the machines ran out in the evenings. Maybe it was normal. Maybe they would be restocked in the morning.

We were feeling a slight tinge of anxiety, but nothing that couldn’t be resolved the next day.

We woke up early as we were taking our biggest excursion of the trip – Appleton Estates, YS Falls, and the Pelican Bar.

We were picked up by our driver, Wings, at 8:00 a.m.

We told Wings of our cash dilemma. He took us back to the banks in Negril.


Machine errors all around.

We told Wings that we might have to go back, we were already down to our last $91 US dollars. We wouldn’t be able to pay him if we couldn’t find a bank that could give us cash – US or Jamaican, at this point, we weren’t picky.

He said, “No worries. We’ll find you a bank. You have $91?”


“Okay, then we’re not cancelling the trip. We’ll make it work.”

So, off we went into the country.

We stopped at every small town bank between Negril and Aberdeen – Machine error…One after another.

I asked Wings if this was typical. If it had happened before? He said he’d never seen anything like it. He said that it must be because of the mandatory closures. People are trying to get everything they have before the government shuts it all down.

He kept calling his friends around the area. He got ahold of someone who told him that they were refilling an ATM in Black River. So, off we went. 20 minutes later, Noah was standing in line for the 12th time. Hoping…Waiting…

He went inside. 10 minutes go by. People are banging on the glass around him.

He comes back to the car. “Did you get it? Are we set?”

“I got a little.”

“A little?”

“Yeah, we can pay Wings… It took me 7 tries to get that much, then I gave up – it was taking too long.”

My heart sank. We had to survive somehow for 5 more days…And all we had was enough to pay our driver – for today.

We went to YS Falls and the Pelican Bar, but there was a huge cloud hanging over us. We tried to play it off and realize that these experiences were once-in-a-lifetime, but the anxiety was palpable.

We were broke. We would soon be stranded.

Friday Night in Negril

Wings took us by the banks of Negril one last time very late on Friday evening. I gave it one last try – success! I was able to get the equivalent of $500 USD in Jamaican money. That would be enough to last until Wednesday. We wouldn’t be “living it up,” but we would be okay.

The Hotel After Dark

Curfews were in place during the entirety of our stay. Curfews in Jamaica were taken very seriously. Late-night revelries would land you in jail, and even cabs had to abide. So, our hotel staff left each day at 7:00 p.m. No restaurants, no bars, no front desk, no shops, no spa, no pool or ocean access….Nothing. From 7:00 p.m. – 7:30 a.m. Silence.

Can I Click My Heels to Go Home?

The United States isn’t allowing citizens to come back from Jamaica without a COVID test, even if you’re vaccinated. So, we were at the mercy of our hotel to provide our COVID test and paperwork to get back to the United States. IF you fail, you’re required to spend 14 extra days at the hotel in quarantine. They made sure to remind us of that several times during our stay. Again, the anxiety was REAL.

Would they forge the test to ensure they always had full capacity?

Would the results be back in time?

They only offered you one test during your stay – and our only option was Monday prior to our Wednesday morning departure.

“You’ll get your results by 5:00 p.m.”

6:30 p.m. rolls around…no results.

Noah is panicked. We ask the front desk – “do you also receive the results? We haven’t gotten our yet, and we were wondering if maybe the email address was written incorrectly?”

“Yes, I have some of them. I don’t have yours yet. Sometimes they run late. Check back tomorrow morning.”

Reminder, the front desk is about to close for the night. We’d have to wait until morning.

A sleepless night.

The next morning rolls around. Still nothing.

We go for a swim. When we arrived back, the email had come through. The front desk would be printing the results.

We were both negative – thank God!

But, when looking at them, the front desk assistant wadded mine up and threw it away.

“Your name is spelled incorrectly. You’ll have to have them fix it. We can reprint it later.”

That was my pass home. In the trash.

We quickly emailed to see if they could fix it. They responded that they would….

Timeline unknown.

Our flight is in 20 hours…

We’ve gotten good at the whole “staying at home” thing this past year, so we watched shows and movies on our iPad every night.

Until the last night.

The same last night that I didn’t have my necessary golden ticket…

There was a thunderstorm in Negril, and lighting struck our hotel. It blasted the phones, the router, the modem, and multiple other devices at the front desk – including credit card processing.

The last night, along with being “room bound” for 12.5 hours, we also had no shows or movies.

I had 12 songs downloaded on my phone from Spotify, and they played on a loop for three hours until we convinced ourselves to go to sleep.

The Final Morning

The thunderstorm meant that we had lost access to everything in the outside world. My COVID test and “pass” back in the United States was not going to happen at the hotel.

My last chance would be at the airport.

We arrived at the airport at 10:00 a.m. No COVID test corrected document.

I was waiting in line to take another test at the airport- my flight would leave at 11:45 a.m.

10:30 a.m. – The corrected form came through. There was no way to print it. I would have to take my chances that the digital document would be good enough.


We rushed through the airport and to our gate. They accepted the documentation, and I was able to board.

Everything could’ve gone so very wrong.

We were so very lucky.

Lessons Learned

Noah and I live life that most stress can be avoided by the 5 P’s – Proper Planning Prevents Poor Performance.

And, most of the time, that’s true.

We kept asking ourselves this trip, what could we plan better? What could have been prevented? What did we learn?

Anthony Bourdain has a quote that was incredibly apropos to this trip, “Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s okay. The journey changes you; it should change you. It leaves marks on your memory, on your consciousness, on your heart, and on your body. You take something with you. Hopefully, you leave something good behind.”

I think that’s what we learned. When traveling, you can’t control everything. And, things can’t always be on your timeline.

You have to put faith in others. You have to ride the waves of what life throws at you. You have to fit into their system, their life.

And, those scars change you as a person. I’m changed after this trip. And, that’s a good thing.

I needed to go 8 hours without money – and without the promise of money to come.

I needed to experience strict travel curfews.

I needed to be at the mercy of a foreign government.

I needed to be fearful of wrongful imprisonment.

Now, I have a better understanding of the fears and anxieties of others.

My pain was temporary. Many people live in this fear forever. How I can make a positive change for THEM?

Travel….Not always pretty….Always eye-opening.

Other Posts on Our Version of Paradise – NYC

As always, don’t forget to Toast The Moon to all of your international travels by visiting our store, and make sure to follow us on FacebookTwitter, and the ‘gram to catch all of our latest posts and adventures!


Majhon and Noah

Leave a Reply