Travel · The Jackson Group

Living Along the Way: Ten Days in Costa Rica

June 2026 • Jennifer Jackson

In January, Mike and I traded a London winter for the green heart of Costa Rica, ten days, three corners of the country, and one quiet reminder threaded through all of it: the whole point of a well-built life is to go and live it.

Arenal, watching over our first mornings.

We started in Arenal, where a volcano seems to watch over everything. Our days began in the thermal rivers at Tabacón water heated by the mountain itself, winding through the rainforest in warm, steaming pools. We floated down the Peñas Blancas River in search of wildlife, walked across old lava fields, and finished one afternoon with a long picnic by the water that I am honestly still thinking about.

Drifting the Peñas Blancas, eyes peeled for whatever the next bend might be hiding.

 

From there we climbed into the clouds. Monteverde is a forest that lives inside the mist orchids, hummingbirds, the rustle of something just out of sight. We walked it by day across swaying canopy bridges, and again by night, when it becomes an entirely different and wilder place.

Mike and me on the Monteverde canopy bridge somewhere in the middle of the best ten days.

 

Costa Rica has a way of slowing you right down. You stop, you look up, and the forest comes to you a sloth dozing through the afternoon, a motmot frozen on its branch, a flower the size of a dinner plate. The forest rewards the people who linger. Of everything we saw, it was the quiet that stayed with me.

Two of the locals a sloth in no hurry, and a motmot mid-pose.

 

I have spent thirty years helping people build plans for their money. But the plan was never the point. The plan exists so that you can say yes to the trip, to the time away, to the people you love and the years you actually get to spend with them. Costa Rica reminded me that a portfolio is a means, never an end. The end is the life: the warm water, the long table, the morning you wake up somewhere new beside someone you love.

So here is the small invitation I carried home. Whatever you are working and saving toward, make sure the plan leaves room to go. Build it sturdy enough to weather the markets and generous enough to fund the memories. That balance security on one side, living on the other is the part of this work I love most.

We spent our last four mornings on the Pacific in Tamarindo, where the days were measured in tides instead of meetings. It was, predictably, the hardest goodbye.

 

Tamarindo: the last four mornings, and the easiest place to forget what day it was.

 

Back among the waterfalls, already plotting the next one.

 

Pura Vida,

Jen 

CIBC Private Wealth consists of services provided by CIBC and certain of its subsidiaries, including CIBC Wood Gundy, a division of CIBC World Markets Inc. The CIBC logo and “CIBC Private Wealth” are trademarks of CIBC, used under license.