By December 2021, the world had endured twenty months of the disorienting COVID-19 pandemic. I found myself single again, living alone (happily), and desperate to break free from the confines of my apartment for a real adventure. With so much of daily life cast into uncertainty, I needed something good to hold onto, something to look forward to.

When an email from Scott’s Cheap Flights landed in my inbox advertising deals to Costa Rica for March 2022, I didn’t hesitate. I booked immediately. Spring break would be the perfect time for this—a break from work and my demanding grad school courses. By then, I reasoned optimistically, COVID restrictions would have eased. What can I say? I’m an optimist at heart.

Dreams of Paradise
I’d dreamed of going to Costa Rica for years. Documentaries and nature programs depicted it as a paradise of untarnished beauty, which excited the romantic naturalist in me. In the US, so much of nature has been tampered with—you can feel the presence of humans almost everywhere except in a few protected places. I was curious to see for myself what life was like in Costa Rica, how people approached living. Would it feel more wild and free compared to American life, which can seem rigid and overly structured? I had to see if this paradise was really all it was chalked up to be.

At the time of my departure, Costa Rica was on the State Department’s Do Not Travel List due to COVID and petty theft. But I decided not to let fear stop me. I’ll admit I was nervous to travel abroad on my own for the first time, but Costa Rica has such a good reputation in the US that it didn’t feel like a huge risk. A few solo female travelers had reassured me that the world isn’t really the scary place news media would have you believe.

I just had to get there first.

Everything That Can Go Wrong
I woke at 4:30 AM to catch my 6:47 AM flight. I rushed to finish packing, start the dishwasher, take out the trash—all the little things you do so your apartment doesn’t reek when you return. My Uber driver was cheerful and determined to keep conversation going despite my groggy state. He was excited for me, happy to be part of this significant moment for a stranger taking their first trip abroad.

At the airport, I headed to the check-in desk. I’d tried checking in online the day before but received an error message saying I’d need to speak with an agent. Before I could get in line, a customer service representative stopped me to check my documentation. I showed my passport and Covid vaccination card.

Then came the question that would nearly derail everything: “Do you have your QR code from the Costa Rica entry questionnaire?”

What?

They allowed me to scan their QR code to access the questionnaire, directing me to step aside and fill it out. Frustrated and without options, I began working through the long form on my phone, anxiety mounting as I watched the clock. It asked where I was staying, but I couldn’t remember the exact address of my Airbnb. I selected a hotel option instead, wondering why the hell I needed to tell authorities where I was staying.

Then I reached the final question: travel insurance information.

I didn’t have travel insurance.

During my trip preparations, I’d come across maybe one or two sources mentioning it, but I’d forgotten to look into it more closely. Nowhere had I encountered clear instructions naming it as a requirement for vaccinated travelers to Costa Rica.

The Breakdown
I walked over to the airline agent’s line, suddenly filled with fear that I might miss my flight—or not make it at all. I explained my situation and pleaded for help. She firmly declared that I must have travel insurance or at least my medical insurance card.

I had medical insurance, but I hadn’t brought the card with me. She looked at me with barely concealed disbelief. “You didn’t bring your medical insurance card?”

This might have been my first time traveling outside the US, but I’d flown around the country many times and never needed to bring insurance of any kind before. It simply hadn’t occurred to me. She suggested I download my provider’s app to find the information.

I stepped away and tried. No luck. I didn’t have the information readily available, and it would take too long to dig it up.

I would have to go home.

That’s when I broke down. I started crying in the middle of the busy airport, contemplating the possibility of complete failure. But I couldn’t give up—not yet. Desperate, I got back in line and spoke to a different agent.

Seeing the state I was in, mascara now smudged around my eyes, she took pity on me. She manually helped me navigate the questionnaire, working her way through the system. When she finally announced that I’d completed the check-in process and handed me my tickets, I breathed a sigh of relief I can still feel today.

One More Obstacle
I walked as fast as I could to security, lugging my heavy backpack filled with my laptop and an assortment of things that wouldn’t fit in my carry-on suitcase. While running my suitcase through the scanner, TSA agents pulled it aside to open and inspect.

I checked the time. The plane was already boarding.

Please hurry.

They took their time inspecting two other bags before mine, my frustration mounting with each second. Finally, they cleared my bag and I jogged to the gate. I was the last passenger to board the flight.

But I made it.

Arriving in Another World

I arrived in San José in the afternoon, around 2 PM. The customs line was long. My backpack grew heavier with each minute as we all inched forward to get our passports stamped and provide dates and addresses of where we’d be staying. This process was made more difficult by the fact that addresses in Costa Rica aren’t as clear and precise as in the US.
After over an hour, I got through and faced my next challenge: finding safe transportation to my Airbnb.

I’d taken Spanish classes in high school and college, and though it had been ten years, I’d brushed up before the trip and felt comfortable with the language. My guidebook recommended buses as the cheapest option, but nothing was clearly marked—even in Spanish—so I couldn’t figure out where to go.

Just outside baggage claim, several taxi drivers waited with signs. A few would somewhat aggressively ask if I needed a ride. I said no to the first two, but after standing around for five minutes looking like a confused tourist, I decided to trust my gut. Somehow, it told me this particular driver was okay.

He definitely charged me a higher “gringo” rate, but I arrived at my destination safely.

First Impressions from the 23rd Floor
The Airbnb apartment in Barrio Escalante offered a bird’s eye view of San José from the 23rd floor of the city’s tallest building. That’s why I’d chosen it. Looking down from the balcony, I felt the rush of free-fall stopped only by a railing.

I was amazed by how loud the streets below were compared to big cities I’d visited in the US. The vehicles and infrastructure seemed to be about ten years behind what I was used to.

Exhausted from my travel woes, I longed for a nap, but excitement wouldn’t let me sleep. I ventured out in search of food, first walking to a grocery store hoping to save money by eating out less. I felt eyes glancing my way as I walked down the street. I tried to maintain a casual expression, developing a backstory in my mind: For all these passersby know, I could be a study-abroad student or on a temporary work assignment.

I bought bananas and supplies for peanut butter and jelly sandwiches—nothing too ambitious.

Being in touch with my Airbnb hosts gave me some notion of safety, but not much beyond that. For an early dinner, I ventured only five blocks to a food court where I ordered a plantain bowl with queso fresco and a sangria.

I’d made it. Despite everything that could have gone wrong, I was here, in Costa Rica, eating my first meal in a country I’d dreamed about for years.

Lessons from Almost Failing
Looking back, that chaotic morning at the airport taught me more than any guidebook could have. Travel—especially solo international travel—requires more than just booking a flight and packing a bag. It demands research, preparation, flexibility, and the willingness to advocate for yourself even when you’re on the verge of tears in public.

But it also taught me about kindness. The Uber driver who was genuinely excited for my journey. The airline agent who took pity on a stressed traveler and helped navigate a complicated system. Even the taxi driver who brought a frazzled tourist safely to her destination.

And perhaps most importantly, it reminded me why travel matters. The walls we live within—the routines, the assumptions, the comfort of the familiar—can only be dissolved by stepping outside them, even when that step is terrifying and complicated.

Sometimes the journey begins not when you arrive at your destination, but in that moment when you decide not to give up, when you get back in line one more time, when you trust that somehow, despite everything, you’ll make it.

Next in the series: Beyond the Tourist Lens – What a Local Guide Taught Me About Costa Rican Sustainability