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I First Visited Costa Rica 33 Years Ago. Here's What I'd Do Differently Today.

Writer: Brian Darling
Brian Darling
Aug 21
2 min read

Updated: Sep 4


Back then, it was a single day off a cruise ship. Ziplining to the beach, cutting through jungle, land crabs skittering across the sand — the kind of day that sticks with you for three decades even though it barely scratched the surface.

I always knew I'd go back and do it right. This year, I finally did. Here's how the two trips stack up.

Then: One day, one stop, no plan. I saw exactly what a cruise itinerary let me see, and nothing more. It was memorable — genuinely — but it was a sample, not a trip.

Now: I picked a handful of regions and actually lived in them for a bit. Costa Rica has beach country, volcano country, cloud forest, and coastline that couldn't be more different from each other depending on which coast you're on. Trying to see all of it in one visit is a mistake I didn't make twice. I'll tell you exactly which regions I chose and why in the guide.

Then: I never left the tourist track. Everything I experienced was pre-packaged, and there's nothing wrong with that for a cruise stop — but it's not the same as meeting the country.

Now: I found where locals actually eat. There's a specific kind of small, family-run spot that's everywhere once you know to look for it — better food, better prices, and a completely different vibe than anywhere near the resorts. I ate more meals at these than anywhere else on the trip, and it changed how I felt about Costa Rican food entirely.

Then: I didn't think twice about safety or logistics. Cruise days are handled for you. This time, I had to actually plan — routes, timing, what to keep out of sight in a rental car. It's a different kind of trip when you're responsible for your own itinerary, and there's one specific safety habit I picked up that I'd tell anyone to build in from day one.

Then: I don't remember tasting anything specific except maybe a soda. This time, food was its own adventure — a national dish I now crave regularly, a coffee culture that earned every bit of its reputation, and one specific drink combination that became a daily ritual by the end of the trip.

Then: I left with a handful of vivid but disconnected memories. Now: I left with an overall rating that landed higher than almost anywhere else I've reviewed — and a very specific answer to "would I go back," because there's more of the country I haven't seen yet.

Some places you visit once and check the box. Costa Rica isn't one of them. Thirty-three years apart, and it still has more to show me.

I put the full breakdown — the exact regions I'd pick again, the food I still think about, the safety habit worth building in, and my complete ratings — in my Costa Rica Pura Vida Quick Guide.

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