Welcoming the Unexpected in Costa Rica

The regression of planning intensity when you take a lot of trips is akin to the regression of grand planning that go into each successive child. With your first child you invent all kinds of rules for producing a well-behaved person. With your second you realize all the mistakes you made raising the first and you adjust your program for the perfect version of your little human. Your third child naturally has the best temperament, and you will mistakenly assume it was your excellent parenting skills honed by the fires of your first two experiments. By your fourth you realize nothing you do matters and you have three other kids to raise anyway and oh god why did we have a fourth?!*

*Full disclaimer: We have no kids.

With our first trip we planned almost every detail in advance to ensure maximum effectiveness. Before we left we had every hotel booked and every travel plan routed. For our next trip we let a friend help with part of the planning, taking some of the burden off of us. But now, after a few trips behind us, we had accumulated many miles under our feet. We know what it will be like more or less, or at least we assume that we do. So there we sat in the San Antonio airport, outside our gate for a flight to San Jose, Costa Rica, searching for a hostel for that very night. Now, we were not exactly rolling the dice and showing up to a foreign country unannounced, but this is pretty darn close to it. We clicked “Confirm Booking” on AirBnB between the boarding of zones two and three. We weren’t exactly panicking as we did it either. Grace was mad, but more so that it took longer than expected and now she had no time to get a Cinnabon.


So happy. So full of Cinnabon dreams. So naive.

We are going to Costa Rica because Grace has always wanted to and I’ve never been, which is basically an insta-yes from me. We had spent the two months after we got married last year in Italy doing farm-stays, trading work on various farms for a room and meals. It was an incredible way to experience Italy – to live off the land and work with Italians for weeks at a time. We wanted that same experience again. So once again without careers, mortgages, (much) debt, or kids we took off to Costa Rica. Unfortunately, not only didn’t we plan a place to stay, we also had no where to work. We got very serious about finding farms, hostels, or hotels that would take us about a week before we left. As it turns out, not many people had space for us. None in fact. These are mostly places of business that operate on a first-come first-serve basis – most needing at least a few weeks notice. The best response we got was an enthusiastic “come on by” from a cute farm outside San Jose. But after our third follow up e-mail we found that they had deactivated their online profile and in a final e-mail said they weren’t a farm anymore. But at least we had our trusty AirBnB for the first night. This, as it turns out, was not the sure thing it was promised to be.

But first, let’s a break from the lows and visit a high. Despite the poor planning involving a room to stay in or a place to work, I did manage to at least prepare for how to get from the airport to the city center while making sure that we had local currency for the bus and the rest of the trip. That was achieved flawlessly. Now back to our regularly scheduled unfortunate event.

We book through AirBnB all the time and usually the follow through happens as advertised. We confirmed that we would arrive around 11pm and our host confirmed that he would be there. We followed our pre-loaded Google Map to the address and after some eyeballing, find our building at around 11:20pm. The house looked fine and had a welcoming switchback ramp leading up to the front door. Between us and the ramp is an 8-foot gate with a buzzer. We rang the buzzer. No answer. We rang again. No answer. Not to worry. We’ve been in this moment before. Grace and I have a bad habit of not getting a local sim card when we are travelling. This means we have to rely on WiFi and apps like Google Hangouts or WhatsApp. We once went from our Paris AirBnB to a distant local bar just because they had WiFi so we could WhatsApp our host that he forgot to tell us the code to get into the building. So this time I pulled up our host’s e-mail and found the WiFi password he so generously sent us in advance. Once I logged in (just enough for one bar since we are some distance from the router) I text and call him. No answer. It doesn’t even display that he’s read the text. After several failed attempts to get anyone’s attention it’s now midnight and I’ve had enough. Under the cover of darkness (and a very scared best friend) I climbed over the gate.


Not really and B & E. More like just an E.

I knocked and rang and called and texted and still nothing. It’s well past midnight when a very sleepy guest stumbled from her room and answered the door. She didn’t know where our host was either but let us in upon seeing our reservation. We navigated ourselves to our room and went to sleep, finally.


The next morning we received an e-mail from a hostel on Workaway.com that initially accepted but then rejected us. The owner told us that while he still did not have room at his rainforest inn, his wife runs a boutique hotel about an hour and a half away from him and she wants take a break and stay with him, but they need someone to run it while she is gone. They need us to RUN the hotel. I should mention here that this is an insane proposition. The only impression this guy has of us is our Workaway.com profile and the brief e-mails we’ve exchanged, and now we will be in charge of his business if we say yes. This is actually a dream come true for Grace and I. Our plan is to open a B&B after our year-and-a-half abroad. We excitedly looked up the hotel and it’s beautiful. It’s a small place, only three rooms, but it has a bird garden and a swimming pool complete with a waterfall. It’s perfect and reminded us of where we got married. We accepted like it was the last lifeboat leaving the Titanic and we’ve had a lifelong dream to row in the cold.

Despite the poor to nonexistent planning, we ended up in a better situation than we could have dreamed up. We are very privileged and lucky to be able to take these opportunities when they present themselves. Part of it is by design, but most of it is just dumb luck. Sometimes the things you think are reliably awesome make you jump over fences to get what you want; other times, management opportunities literally fall into your laptop. It’s impossible to plan for, but it’s always exciting to see what kind of surprise is in store. I can’t wait to see what running a hotel is like.

Plane tickets:
Bus tickets: $3
Food: $1.50 (not a Cinnabon)

8 thoughts on “Welcoming the Unexpected in Costa Rica

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