The Promise I Made My Kids — And How It Changed Everything
When my kids entered high school, I made them a promise: every year they’re in high school, I will take them on one one-on-one trip anywhere in the world they want to go.
No siblings. No compromises. Just the two of us.
At the time, I didn’t fully realize how transformational that promise would become — not just for them, but for me.
Freshman Year: Costa Rica with Liam
My oldest, Liam, was first up. For his freshman-year trip, we chose Costa Rica, and it set the bar impossibly high.
Our itinerary was perfectly paced and wildly memorable:
Flew into San José
Drove to Mount Arenal
Continued on to the Cloud Forest
Finished in Quepos, one of the coolest fishing villages I’ve ever visited
Because Liam was older, physically capable, and free of height or age restrictions, we got to say yes to experiences that would’ve been impossible with younger siblings in tow:
Zip lining (absolutely terrifying for me, by the way )
Mountain biking
Paddle boarding
Deep sea fishing
Ziplining in Costa Rica
That zip lining experience stands out to this day — not because I loved it (I didn’t), but because it was something new and scary we experienced together. Those moments bond you in a way everyday life just can’t.
But honestly? The most powerful part wasn’t the adventure. It was the uninterrupted conversations. No younger siblings cutting in. No distractions. Just time to really listen and get to know who my son was becoming.
Sophomore Year: Roughing It in Antigua
Liam’s sophomore-year pick was Antigua, and we did it very differently.
We rented a car and stayed in a simple Airbnb right on Dickenson Bay, one of the most famous beaches on the island. Having our own car meant total freedom — and total adventure.
The roads? Sketchy at best. Some literally ended and dropped off into the sea.
But that freedom let us explore every corner of the island:
Multiple trips back to the area near Hercules Pillars — we loved the snorkeling and the restaurants
Hiking the Shirley Heights Trail
More deep sea fishing
Shirley Heights Trail
It wasn’t luxury travel — it was real, gritty, memorable travel. And letting Liam choose not just the destination, but how we experienced it, made the trip even more meaningful.
Kyler’s Turn: Soccer, Culture & the UK
My younger son, Kyler, has very different interests — and that’s where these trips truly shine.
His freshman-year trip? The United Kingdom, built entirely around Premier League soccer.
We blended sports and culture:
Explored London extensively
Took the train north to Manchester to see additional matches
Mixed stadium days with museums, walking tours, and city exploration
We even found some unexpected highlights like:
Play Activate (https://playactivate.com)
The Snow Centre near Manchester
It was the perfect example of seeing the world through his eyes — following his passion while still layering in culture, history, and learning.
Why One-on-One Travel Is Such a Gift
These trips aren’t just vacations.
They are:
Space for deep conversations
A chance to focus on their interests
Time to really see who they are without sibling dynamics
Shared memories that belong to just the two of us
Yes, we usually pull them out of school — but we always build learning into the trip. Geography. History. Culture. Environmental awareness.
I’m incredibly proud to say my kids are confident travelers. They:
Navigate airports and cities (even without phones)
Exchange currency
Read maps
Talk to locals
Understand cultural differences
We also try to include some kind of environmental or cultural lesson on every trip — whether that’s conservation, local history, or learning how tourism impacts a place.
This Year: Two Kids, Two Trips
This year is a big one — and an expensive one — because I have two kids in high school at the same time.
Liam and I are heading to Banff, Canada for a winter escape
Kyler and I are off to Barcelona, returning to Europe for soccer — this time to see the newly renovated stadium, plus plenty of history
And my youngest daughter? She already has her future trips planned:
An African safari to see the big cats
The Galápagos for wildlife
New Zealand to skydive (God help me)
Final Thoughts
If there’s one thing these trips have taught me, it’s this:
Time and attention are the greatest gifts we can give our kids.
Travel just happens to be the vehicle that makes those moments deeper, richer, and unforgettable.
Watching the world through their eyes — without compromise — is something I’ll treasure forever.
