Why My First Solo Trip Was Costa Rica

I didn’t pick Costa Rica off a bucket list. I picked it because it was the path of least resistance.

My dad’s wife is Costa Rican and her mother still lives in San José. That meant a free place to stay for my first couple of weeks. Costa Rica is also close to the US, so if the whole thing went sideways I could be home fast and cheap.

That was the entire selection process. Free bed, short flight. No soul-searching, no map with pins in it.

I mention this because most first-solo-trip articles start with someone hearing a call from a place they’d dreamed about since childhood. Mine started with a spare bedroom and a short flight. If you’re waiting for the destination that speaks to you, you might be waiting on a feeling that isn’t coming. Pick the one where you already have an advantage.

The two weeks before I left

I wasn’t nervous, which surprised me.

I kept waiting to spiral about it and it never happened. What I felt instead was something closer to being lit up. I’d finished my degree, my lease was ending, and for the first time in years there was nothing I was supposed to be doing.

That wasn’t courage, though. I had a free place to land, a return flight I could afford, and no dependents. The fear people describe before a first trip is usually proportional to what they’d lose if it went badly, and at that point I’d already lost most of it.

San José

The first two weeks were a soft landing and I knew it while it was happening.

I walked a lot. Sat in cafés. Ate things I couldn’t identify. Did the touristy stuff. But I also got something most travelers don’t get, which was a family. My dad’s wife’s extended family took me in immediately. There was a big barbecue where I helped cook and met cousins and neighbors who had no particular reason to be that generous with a stranger and were anyway.

Two weeks of that is a very gentle introduction to being alone in a foreign country, and it’s most of the reason I never had the crisis moment that first-trip stories usually feature. I got to acclimate to the language, the pace, and the money before I had to do any of it by myself.

I’ve never forgotten that travel is a privilege. That’s not a disclaimer, it’s just true, and I got a bigger head start than most.

Puerto Viejo

After those two weeks I found a Workaway posting at a hostel in Puerto Viejo, a slow Caribbean beach town on the southeastern coast. I stayed ten weeks.

The deal was about 25 hours a week in exchange for a private room. And when I say private room, I mean a bed with a narrow strip of floor beside it. That was the whole room. It was also the first space in months that was mine, and I liked it more than any apartment I’d rented.

Mornings were coffee for the guests, filling the giant water filter, stripping beds for checkouts. Then a long dead stretch until the afternoon arrivals showed up and I’d check them in, take payment, assign bunks.

Two full days off a week, though the distinction between working and not working blurred almost immediately. There were afternoons I couldn’t go to the beach with everyone else. I was never more than an hour behind them.

The rest of it was swimming, street parties, and walking the beach at night. Lunch was almost always empanadas from the cart I could see from the hostel’s front door. Beef, lentil, pineapple, sweet red bean. I rotated between chicken and sweet red bean. A dollar each, and not small ones, either.

That’s the part I’d want you to understand about work exchange. It isn’t free travel. You’re trading labor for a bed, and some days the labor is real. But it buys you something a hotel can’t, which is a reason to be somewhere for ten weeks instead of four days, and a set of people who are also there for ten weeks.

The hardest part

The goodbyes, and it wasn’t close.

You meet people at a pace that doesn’t happen in normal life. Everyone has arrived alone, everyone is slightly outside their own context, and the usual scaffolding people use to keep each other at a distance just isn’t there. You get to know someone properly in about four days.

Then they leave. Or you do.

I’ve kept up with a few. I’ve visited one or two since. Most of them are just memories at this point, which is a strange thing to accept about people you’d have called close friends at the time.

That’s the real cost of this kind of travel, and there’s no line in the spreadsheet for it.

What it actually taught me

The tidy version of this story is that I went to Costa Rica and came back transformed. That’s not what happened.

At the time I thought I was on a long vacation before starting a career. I came home and immediately opened a retail store. I was not walking around Puerto Viejo having realizations about the nature of freedom. I was checking people into bunks and eating empanadas.

It took me years to understand what those four months had actually done. They didn’t change my life on the spot. They quietly changed the baseline of what I thought a good life required, and then sat there, unused, while I spent the next several years trying to build a conventional one.

I’m not going to tell you to trust the universe. What I actually got out of it was smaller than that. I found out I could handle being somewhere unfamiliar without a plan, and that a life with almost nothing in it could feel full. That information doesn’t do anything for you immediately. It sits in the back of your head and makes it harder to believe things you used to believe.

If I have advice, it’s only this. Don’t wait for a place to call you and don’t wait to stop being scared. Pick the trip where you have the most advantages, go, and don’t expect it to mean anything until much later.

I didn’t know it was the start of anything.

It was, though.

If Costa Rica is on your list, my Costa Rica page has three routes, from six days to sixteen. Drop your email below if you want to follow along. The day-to-day goes on Instagram.

Thanks for reading

Get the next one on the 1st.

I’m Dylan. One honest email a month: what it cost, what worked, and the places worth your time. You also get my free field guide, First 24 Hours in a New Country.

Sign me up

Free. Unsubscribe in one click.