How We Knew Our Kids Were Ready for a Safari in Kenya

A Guest Post By LeeAnn Stivers

We always imagined we would raise our kids to be travelers. In practice, that looked a lot like

movement close to home: road trips, camping, coastal weekends, Whistler, Mexico. We kept

moving, but there is a difference between enjoying travel and fully committing to a big trip. For a long

time, anything that required real distance or a long-haul flight quietly lived in the category of

“Someday.”

Kauai was the first time we stopped talking about someday and simply went.

What changed was not the destination, but the way we experienced it. We found a rhythm that

worked for all of us, with days layered with waterfall hikes, snorkeling, sailing, and jungle trails,

balanced with long stretches of unstructured time. The boys had space to be fully themselves,

crashing into waves, digging in the sand, chasing whatever caught their attention. It was the first

time we saw how adventure and rest could coexist on a far from home trip in a way that felt sustainable for our family. We departed Hawaii knowing two things with clarity: water is where we come alive, and we our family was ready to go further.

Costa Rica became that next step.

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In 2024, when the boys were six and ten, Costa Rica marked a shift from vacationing to

traveling. It was not just a change in geography, but in expectation. We were asking more of

our kids, such as to sit through longer drives, to try unfamiliar food, to stay present with guides and

experiences that did not immediately gratify but required effort to obtain. At the same time, we held onto the elements from Hawaii that mattered for them: space to reset, to play, to return to something familiar at the end of a full day.

The end result was true magic. Our boys leaned-into the Costa Rica trip with a level of curiosity and engagement we had not fully seen before. They asked thoughtful questions of their guides and us, listened closely, and actively sought out the experience: tracking poison dart frogs, zip lining through the canopy, and pausing to watch a new mother sloth care for her pup just after birth. They threw themselves into surf lessons and immediately wanted more, played with Spanish by attempting new words with locals, and approached unfamiliar food with a level of openness we had not expected. They were not just participating; they were paying attention. As a Mom, watching that unfold was a dream come true.

Costa Rica answered a question - were we raising children who could be good travelers, not just vacationers? The answer was yes, and it created the confidence to take a much bigger step.

This year, that step is Kenya. It’s more like a leap, but it feels right for our family at this time. My husband Jeff has traveled to Africa more times than I can count on my hands, but his connection to the continent goes back much further than his nearly 20-year career in the travel industry. He studied abroad in Tanzania during college, spent time in the Sahara and on the Nile working on archaeological digs, and has been designing and selling travel across the region since his mid-twenties. His relationship with and love for the African continent has been built over decades, not just visits, and it’s been his dream to share his passion for Africa with us. 

Most importantly though, we are seeing the readiness in our kids, and beginning to feel, as parents, the quiet awareness of how few summers we have left with them. Their readiness shows up in curiosity and excitement for the trip on the horizon; ours in the willingness to trust, to let go of some control, and to say yes to something that will stretch all of us. 

The Kenya itinerary we’ve built together reflects that balance. We begin in Nairobi at House of Waine, offering a gentle entry point and proximity to the Giraffe Centre, an immediate, tangible way for the boys to engage with the wildlife they will encounter later from a further perspective. From there, we fly up north to the Ol Lentille Conservancy, where the landscape opens into vast, uninterrupted views that shift your sense of scale. As Jeff has shared, time on the conservancy invites deeper engagement through wildlife tracking, guided walks, and opportunities to connect with the Samburu and Maasai cultures in ways that feel both accessible and adventurous. It is the kind of place where our shared curiosity naturally takes over and we can explore together.

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The journey continues into the famed Maasai Mara wildlife reserve, where we split our time across two camps that offer cultural depth, safari time, and space to slow down through early morning game drives, afternoons back at camp, and the kind of wildlife moments that Kenya is famous for. Our trip was designed to progress in a way that will build our kid's confidence as travelers: enough adventure to keep them curious, enough structure to give Mom & Dad a plan, and plenty of space for quiet downtime and reflection. We’ve purposefully built in room within the itinerary for them to choose their own activities (not everything needs to be scheduled) and are equally intentional about how we live while we travel, making sure everyone has space to recharge at the end of a long day. It is a simple formula, but it is what allows us to keep stretching further. You can glimpse our itinerary and trip plan at the link below.

VIEW OUR FAMILY KENYA TRIP

We are still learning what truly immersive travel looks like for our family. Each trip teaches us something new, about our kids and about ourselves as parents. Kenya feels like the right next step in that ongoing process, not because we have it all figured out, but because we are ready to keep discovering what is possible together. 

Next comes the part that matters just as much: how we prepare for a trip like this. Stay tuned!

The Stivers Family is headed to Kenya in November. Follow their journey on our Instagram (@outlier.journeys) for get in touch with Jeff at jeff@outlierjourneys.com to discuss your own Family Adventure to Africa.