‍How it all started

When I first pitched the idea, most people said: “You’re nuts.” It was mid-pandemic. Travel was a logistical Rubik’s cube. But when I floated the idea to Nick and Sebastian, their response was instant: “F** it, let’s do it.”*

Landing in Costa Rica: Rain, Coffee, and Adrenaline

We flew into Liberia and immediately headed up to Monteverde in the mountains. None of us really knew what we were walking into…

Monteverde was…moody. Chilly, wet, foggy. I had packed exactly zero warm clothing. Just shorts, t-shirts, and a cast on my arm. Picture me wrapped in a hostel blanket wearing a poncho meant for toddlers.

Still, we made the most of it.

We worked a little (shoutout to “remote” software sales), but mostly just tried to soak up the vibe. And the ziplining? Next level. Flying over lush rainforest canopies, wind and rain in our faces—it was the kind of adrenaline rush you only get when you’re strapped in with a questionable harness and a GoPro dying midair.

That zip line run was hands-down my favorite moment from Monteverde.

We also met some characters—Matt and Rob, who would pop back up later in Tamarindo. A couple flight attendants. Some local guides who gave us real talk about Costa Rica’s laid-back but fiercely proud culture.

But after a few days of wet clothes and cold toes, it was time to chase the sun.

Tamarindo: Where the Real Trip Began

We hit the road and headed west to Tamarindo, a beach town that would go on to become the true heart of this bucket list journey.

The second we rolled in, it felt like we exhaled.

Sun. Salt air. Streets full of locals and expats riding bikes with surfboards under one arm. Even during COVID, Tamarindo had life. A kind of buzz. And because of the pandemic, we kept seeing the same 10-15 people on the beach, at the hostel, in the bars. It became this tight-knit, weird little bubble of travel friends and strangers-turned-characters.

We stayed at Casa Aura—a hostel so good it deserves a shrine. Right on the beach. Solid breakfast. A restaurant below called “Salad Agua” that served this fried snapper I still dream about.

Days were for beach walks, jet skis, beers, and naps in hammocks. Nights were for wine bombs, pool games, and some truly unhinged moments I can’t (and probably shouldn’t) explain here.

There was the guy who had just gotten out of prison. A screaming redhead demanding $7 from Sebastian. Me trying to play it cool and casually scurrying away like a cartoon mouse. Classic.

At one point, I even managed to take a girl home who got so drunk I had to walk her back, clean her up, then go back to the party. Which I did, because I’m a man of the people.

Pura Vida and the Mayor of Tamarindo

If you’ve ever been to Costa Rica, you’ve probably heard the phrase “Pura Vida.” It’s more than a saying. It’s a whole damn philosophy.

It means “pure life,” sure—but it feels like “slow down, chill out, enjoy this moment.” That vibe runs through everything: the people, the food, the way no one’s really in a rush. It’s hard to explain, but easy to feel.

We even created a shared doc called “The Pura Vida Boys,” where we logged our most ridiculous moments, running jokes, and hostel folklore. My broken thumb got its own subplot. So did the “Mayor of Tamarindo,” a local dude who somehow knew everyone and was both hilarious and terrifying at the same time.

This place gave us what we didn’t know we needed: fun, freedom, and a reset on life.

A Plot Twist Called the Four Seasons

Just when you think the bucket list is all backpacker hostels and beer money, we decided to flip the script.

Nick pitched the idea: “What if we just go full baller and stay at the Four Seasons Costa Rica for a few nights?”

I laughed. Then I checked my bank account. Then I said yes.

It was the perfect shift in energy.

The resort was practically empty—thank you, COVID—which meant we had two beaches, endless piña coladas, and golf carts on demand all to ourselves. I read under a cabana while Sebastian journaled and Nick floated in the pool like a man who had truly arrived.

It was reflective. Peaceful. A different kind of bucket list box checked.

Every Squirrel Got His Nut

We each got something out of it:
Sebastian finally got his slow-travel zen moment.
Nick fulfilled his dream of staying at a luxury beach resort.
And me? I got to look back on the trip and realize—this thing actually happened.

We pulled a country out of a hat (sort of). We booked flights. And we lived it.

Bucket Lists Don’t Need to Be Perfect—Just Lived

If I’ve learned anything from trying to cross off 52 life goals in one year, it’s this: you’re never going to follow the script exactly.

Countries change. Plans shift. Thumbs break.

But if you show up, say yes, and let the story unfold—that is what makes it a bucket list memory.

This trip was wild, weird, sometimes uncomfortable, but always worth it. It brought three old friends even closer. It gave us stories we’ll tell for decades. And it reminded me why I started this whole project in the first place.

To feel alive.

To take the chance.

To do the damn thing.

🎧Listen to our podcast episode for the unfiltered, hilarious, and heartfelt version of this story. 

Got a bucket list idea you’ve been putting off?

If you’ve ever dreamed of doing something wild, spontaneous, or off-script, this is your sign.

You don’t need the perfect plan. 

Write it down. Speak it out loud. Grab your people and go.

Someday you’ll be telling your own wild story.

And if you’re looking for a tool that can help, head over to BucketMatch to start your bucket list journey today.