
Nicaragua · Where I stayed
Outsite San Juan del Sur
A quiet base to lock in and work, with the bay and sunsets right there.
Two months of work, new friends and an ambitious board rental
In autumn 2024, I spent about two months in Nicaragua and Costa Rica. First San Juan del Sur, then Santa Teresa. I stayed at Outsite the whole time, worked, explored, made some good friends, and went surfing in both places.
Most days were ordinary workdays with a better view. Around them came beach runs, sunset horse rides, and friendships that followed me home. I also gave surfing one last proper try. The photos make that part look more successful than it was.
Nicaragua came first. San Juan del Sur was my base, with work taking up most of the days and exploring and meeting people around it. Surfing was part of the trip here too, though Costa Rica would be where I gave it the most serious try.
The people were lovely too. On my birthday, someone lured me back from the gym, and I walked into the kitchen to find everyone waiting with a cake. I'd only come back expecting the usual post-gym hunger, so this was a considerable upgrade. Being far from home felt a little less far that day.
San Juan del Sur made it easy to settle into a slower rhythm. I still had work to do, but finishing for the day felt different when I could spend the evening by the bay. I could happily have stayed longer.

Nicaragua · Where I stayed
A quiet base to lock in and work, with the bay and sunsets right there.


Going out · San Juan del Sur
Hostel PachamamaThe starting point for the infamous Sunday Funday pool crawl.


Nacho is closed now, but still deserves a mention from this trip.
From Nicaragua I went to Santa Teresa in Costa Rica. This was the next chapter of the trip: beach runs, new friends, sunset rides, and another attempt at becoming a surfer. Plenty to fit around a normal working week.
I stayed at both Outsite locations, which gave me two different versions of life here: the view from up the hill at Maramar, and the more social atmosphere at Playa. Between them, I found a routine I could happily have kept going for a while.
Flying is an option, but I'd recommend arranging a private driver. It's easy, and you get to see a lot of both countries along the way. Just remember that you cross the border on foot. With tonnes of luggage, that part can get sweaty 😅
Across the two countries, I was mostly working. The deadlines came with me, unfortunately. They apparently don't recognise a change of scenery.
Still, I liked having somewhere beautiful to come back to between tasks. It made an ordinary working week feel like part of the trip, rather than something I had to get through before the trip could start.
Santa Teresa was expensive. Housing and restaurant prices felt similar to New York and San Francisco. A beach town, yes, but I wouldn't go there expecting a cheap couple of months.
ATV life
Getting around added another chunk to that budget. ATV life was fun, but the prices I saw could reach USD 80-100 per day in peak season. In the off season, you might get lucky with USD 50.
That adds up very quickly when you're staying for weeks. I liked the freedom, but the quad was making a serious attempt at becoming my biggest travel expense.
I made some really good friends during those two months. Having people to share the everyday bits with made a huge difference. After a while, it felt less like passing through and more like having a small life there.
Danny, Connor, Murat, and Matt stand out the most. Danny and I later caught up in San Francisco and even Norway. Some friendships travel well beyond the place where they started.
For going out, Somos was the Thursday and Saturday party spot while I was there. Kooks was another place to go out.
I also went to an ecstatic dance at sunset. Not entirely sober, admittedly, but definitely enthusiastic.
My friend James is a filmmaker and a considerably more successful surfer than me. We also came up with an AI-generated mascot together as a group: the "Kook" monster, a blue furry creature surfing with a beer in hand. Like Kooks, the bar. Even our made-up mascot was doing better on a board than I was.




You can also go diving around Santa Teresa and Malpais. There are other ways to spend time in the water if surfing isn't your thing.
Maramar had the best view. It is up the hill, so I would definitely rent a quad if staying there. Playa felt more social. I liked getting to try both.

Santa Teresa · Best view
My favourite view of the two. It is up the hill, so I would definitely rent a quad.

Santa Teresa · More social
The more social of the two Outsite locations. I liked getting to try both.
I was also running 5Ks on the beach quite regularly in Santa Teresa. That part of the beach routine stuck a little better than the surfing. The sunsets certainly helped.
We also went horseback riding along the beach at sunset. This was one of those evenings that made me very glad I'd come. No great plan or ambition, just a really good time with people I liked.
It also helped that the horse was handling the difficult part. After my attempts at surfing, it was nice to let someone else be in charge of staying upright.
On a hike down at Montezuma Falls, near Santa Teresa, we took off our shoes to cross the river. On the other side, I figured I would take ten barefoot steps to dry my feet a little before putting my shoes back on.
What could possibly go wrong in ten steps?
On step nine, a caterpillar fell onto my pinky toe. It hurt like hell.
I took a photo and sent it to ChatGPT, which suggested it might be venomous. Not quite the answer I was hoping for. I didn't have insurance at the time, which made the whole thing considerably less funny while it was happening.
I tried to reassure myself that my pinky toe was about as far away from any important organ as it could get. Luckily, everything turned out fine.
I got insurance the next day.
Some people jump from halfway up the waterfall, or even from the top. I'd prefer a parachute from that height 😅 Swimming around the waterfall and jumping through it is popular too, and gets my recommendation.
In Costa Rica I rented a board and an ATV and got in the water every second or third day. This was my last earnest attempt at the surfer-boy thing. I gave it time, had fun, and kept going back.
By the end, I was still pretty bad. There isn't much point dressing that up. I'd given the surfer-boy idea a fair chance, and the ocean had given me fairly consistent feedback.
I used to think surfing would become a hobby. I think I wanted the image as much as anything. I've made my peace with downgrading it to an activity.
I still find it fun. If the waves are good and there's a board available, I'll probably head out. I just won't be organising my life around it any time soon 😅
Arenal, the trip I didn't get to take
I also wanted to visit
Arenal
, the volcano near La Fortuna, with rainforest and hot springs around it. In the end, I was whisked away abroad for work before I could go.
From Santa Teresa, I'd look at renting a 4×4 for the freedom to explore, or booking a
local driver
to take you to La Fortuna. An adventure either way. It's the trip I'd make time for next time.
A reminder to stop saving everything for later. You never know what tomorrow might bring, or where you'll end up spending it.
Three memories, blended with AI.
A few more trips from the archive.
Red dirt, sea turtles and a Jeep Wrangler
Backpacking Sydney to Cairns, twice
South to North