Life In Costa Rica

How We’re Doing This Long Term

People ask us all the time “so how are you actually allowed to stay?”. The answer is actually that we’re doing it two different ways, for two different reasons, and neither of us are doing the “visa run every 90 days” thing.

Why I didn’t want to do visa runs

There’s some expats out there that do what they call “visa runs”, leaving the country every 90 days (or 180, depending on what the current entry rules are), and coming back in on a fresh stamp. It’s not a bad solution for some people; it just wasn’t for me. Between teaching and my daughter’s school schedule, I didn’t want our lives to be ruled by the border runs. Something many people don’t realize going into the job search is that not every school sponsors the work visa. Two of the schools I got offers from didn’t sponsor the work visa at all. If I’d taken either of those, I’d be doing border runs every few months, tourist stamp to tourist stamp, indefinitely. That was a big part of what led me to the cloud forest school. The cloud forest school does sponsor the work visa, directly tied to my teaching position, and that definitely put it on my short list. How it’s actually working is that I came into the country on a tourist visa, and once the school’s attorney formally starts my work visa process, I’m allowed to legally stay past the 90 day limit on a tourist while it’s pending. I don’t have to do border runs while the application is going through (which, it turns out, is a process that takes six months to a year). The paperwork surprised me more than the timeline did. I needed an apostilled birth certificate and FBI background check. Both had to be done in person, which for us meant a trip to the state capitol in Austin, TX, since those are things where just mailing it in wouldn’t cut it.

Why my husband is going the investor route instead

My husband is a bit of a different case. His offshore oilfield schedule makes for long stretches out of the country, and that makes for routes that have in-country presence requirements or have long processing timelines that hinge on staying local to be a poor fit for him. The investor residency (Inversionista) route made more sense for him.

Here’s what that route actually requires, based on the current 2026 rules:

A minimum investment of USD $150,000, which can go into real estate, a registered business, shares, or an approved project
If the investment is real estate, it has to be in his personal name and not held through a company in order to qualify
It starts as a two year temporary residency, renewable as long as the investment is maintained
After three years of continuous legal residence, he can apply for permanent residency
Investors can include a spouse and dependent children in the application. Exactly the plan. Once his residency is approved, he can claim us as dependents, and I won’t need to keep working just to maintain my own status here.

It’s a bigger financial commitment up front, but for someone who’s out of the country for weeks at a time, it’s the route that fits his life rather than fighting it.

Where things stand right now is that we’re still in process. Aside from the car, we haven’t purchased anything yet towards the qualifying investment. That part of it is still ahead of us. Slower than either of us would like, but it’s happening.

What being on the Caja actually means

I’m registered under the CCSS (Caja Costarricense de Seguro Social), usually just referred to as “the Caja”. It’s Costa Rica’s public healthcare and social security system, and being enrolled means I have access to public clinics and hospitals here, the same system Costa Rican citizens use. Contributions come out based on income, similar to payroll taxes back at home, and it covers everything from routine doctor visits to major medical care. It’s not private insurance, and the pacing of public healthcare here has it’s own rhythm compared to what we were used to, but it means real, functional healthcare coverage without paying out of pocket for every visit.

The bigger plan

This isn’t just about the paperwork. It’s about where we’re headed. He’s hoping to retire from the oilfield within the next five years. The investor visa isn’t just a legal workaround for his work schedule, it’s step one of an actual long term plan to be here, together, full time, sooner rather than later.

If Costa Rica doesn’t work out

We’re realistic about this. We chose the path we’re on carefully, but we also built it so that if Costa Rica ultimately isn’t the right long term fit, we haven’t lost much. Colombia is our next option if things don’t pan out here. It’s not a doomsday backup plan, it’s just how we think about this whole move. We’re not locked into one country out of sunk cost thinking. We’re looking for the place that actually works for our life. What we have in common is that we don’t see ourselves moving back to the States anytime soon. That’s not part of the plan. Our real end goal is a second, permanent residency somewhere outside the U.S. – a real, legal foothold in a country we choose, rather than just an extended vacation. Costa Rica is where we’re building that first. Colombia is the next name on the list if we need it.

The part that made it manageable

Honestly, the thing that’s kept us from being completely overwhelmed by this is having the right person handle it. The school’s attorney is our POI (point of contact) for the whole process, and he handles about 90% of the actual paperwork to go through it for us. Out of the full process (which involves 11 hearings total), we only need to personally show up for 3 of them. He handles the rest for us. If you’re going through this, I can’t overstate how much having a good attorney makes the difference between drowning in bureaucracy and just… waiting.