The best travel lesson I’ve ever experienced didn’t happen on a trip.
It happened in a classroom.
Over the years, I realized something surprising: the skills that make someone a great student are often the same skills that make someone a great traveler.
In a good classroom, learning isn’t just about finding the right answer. It’s about curiosity. Asking better questions. Sitting with uncertainty long enough to understand something more deeply.
I’ve seen this happen many times with students.
A student reads about the Roman Empire in a textbook, memorizes a few dates, and moves on.
When they stand inside the Colosseum, they suddenly start asking completely different questions.
- How did people feel sitting here?
- Why did a society build something like this?
- What did power look like in this world?
The facts didn’t change. But the experience changed the way they thought about them.
It’s one of my favorite moments as a teacher: when a student stops looking for the right answer and starts asking a better question.
Many times, those moments happen on the road.
During a civil rights trip, we visited 16th Street Baptist Church in Birmingham, Alabama, where four young girls were killed in a bombing in 1963. Students had read about the event in class. They knew the names, the date, and the role it played in the movement. But standing outside the church made it feel different.
“Mr. Voss… we talked about this in class. But something about being here. It just lands differently.”
Moments like that remind me what curiosity really looks like. Travel doesn’t just give students answers. It gives them better questions. Learning stops being abstract and becomes personal.
The same skills that make someone a thoughtful learner—curiosity, empathy, and a willingness to see the world from multiple perspectives—are exactly the skills that make someone a thoughtful traveler.
Moments like that don’t just teach content. They change something deeper. Students don’t just see the world differently—they begin to see themselves as part of it, with a greater awareness of the people, histories, and communities around them.
Teaching has shaped the way I think about the world, about people, and about the value of experience. And in many ways, those lessons now shape how I approach travel.
At first, I planned school trips before I ever called myself a travel advisor. Watching students encounter a place they’d only read about, and seeing something shift in how they understood the world, showed me what travel can really do. It’s what led me to start Tenured Travel, and it’s the lens through which I plan every trip today.
Here are a few things the classroom taught me about seeing the world.
Every Destination Has More Than One Story
In any classroom, no two students arrive with the same story. Each person brings their own background, perspective, and experiences that shape how they see the world. A student who grew up hearing one version of a place will see it completely differently from someone who grew up hearing another.
It’s one of the most dynamic and essential parts of a classroom because learning to understand different perspectives is one of the most important skills a student can develop.
Travel works the same way.
No destination has just one story. A place is not just what appears on a postcard, a travel list, or a viral Instagram post. It’s a collection of perspectives, histories, and everyday lives that exist far beyond what most travelers see.
Two people can visit the same place and walk away with completely different experiences.
That’s part of what makes travel so powerful. It reminds us that the world is bigger, more complex, and more interesting than any single narrative.
I was reminded of this while walking down Auburn Avenue in Atlanta—the street where Martin Luther King Jr. grew up and was once the most prosperous Black business district in the country—you can still see pieces of that history. Churches, storefronts, historic buildings that tell the story of what was once called “the richest Negro street in America.”
But you also notice something else.
An interstate now cuts directly through the area. The flow of the neighborhood is broken. Some buildings stand beautifully preserved, while others show signs of neglect and time.
Standing there, it makes you start asking different questions.
- How and why did this place change over time?
- Who benefited from those decisions?
- What stories are told—and which ones are harder to see?
Moments like that remind me that history isn’t just something we read about. It’s something written into the places around us.
The version of the story students and I arrive with is often incomplete. Seeing the places where it happened, and the people living there today, reveals how much more there is to understand.
And that understanding begins with something simple: the willingness to see a place from more than one perspective.
That’s part of what makes travel so powerful. It reminds us that the world is bigger, more complex, and more interesting than any single narrative.
The Danger of Arriving with a Single Story
One of the most important ideas I return to, both in the classroom and in travel planning, is what Nigerian author and educator Chimamanda Ngozi Adichie calls the danger of the ‘single story’. If you haven’t seen her TED Talk, it’s worth 20 minutes of your time.
The core idea is simple. When we only hear one version of a place or a culture, we risk turning complex communities into simple stereotypes. Headlines, social media posts, and travel lists often reduce destinations to one idea or one image.
Travel challenges that.
When you visit a place yourself, you quickly realize how layered and nuanced it really is. A city is not just its famous landmark. A country is not just the reputation it carries in the news.
I noticed this almost immediately during my first trip to China. Much of what I had heard about the country before arriving came through political headlines. But the moments that stayed with me were much quieter.
One morning in Beijing, I walked through a park and saw groups of older residents exercising together. Some were stretching. Others were practicing tai chi. A few were simply walking and talking with friends as the day began.
It felt routine. Almost ordinary. But it also revealed something deeper about the rhythm of daily life.
Many retirees in China step away from full-time work earlier than Americans might expect. In part, this helps make space for younger generations entering the workforce. At the same time, there is a strong cultural expectation that younger family members help care for their elders.
The result is a different relationship between generations. Health, family, and community are not seen as individual responsibilities alone. They are shared ones.
Watching those morning routines reminded me of something important. A country is never just the story we hear about it. Sometimes the real story is happening quietly in a park at 7 a.m.
The headlines tell one story. Everyday life tells another.
The more you travel, the more you begin to appreciate the many stories that exist within a single place.
Curiosity Matters More Than a Checklist
Students learn best when they are curious.
The same is true for travelers.
Many people approach travel with a checklist of attractions they feel they need to see. While those landmarks can be incredible, the moments people remember most are often the ones that weren’t planned.
- A conversation with someone local.
- A neighborhood café you stumbled into.
- A street you wandered down because you simply wanted to see what was there.
I remember wandering through the Gothic Quarter in Barcelona, Spain with no particular destination in mind. Turning down a quiet side street, I ended up in a small square called Plaça de Sant Felip Neri.
At first it felt peaceful. Just a small fountain, a few children playing, and old stone buildings surrounding the plaza. But looking closer, you start to notice something unusual. The walls of the church are rough and marked with dozens of small scars in the stone.
I wondered what had happened there. They aren’t from age or weather.
They’re the marks left behind from a bombing during the Spanish Civil War that killed dozens of people, many of them children.
It’s the kind of discovery you rarely find on a checklist. But curiosity has a way of leading you there. You notice something small. You start asking questions. And suddenly a quiet plaza becomes a doorway into a deeper story about the place you’re visiting.
Moments like that change how you see a destination. History stops being something you read about and becomes something you encounter in the places around you.
As a travel advisor, part of my job is building itineraries that leave room for exactly those moments. I design a structure that creates space, rather than filling every hour.
Curiosity opens the door to experiences that no guidebook can fully predict.
The Best Learning Happens Through Experience
As a teacher, I’ve always believed that the most meaningful learning happens when people experience something for themselves.
Reading about history is valuable. But standing in the place where history happened creates a different kind of understanding.
I remember visiting the Great Wall of China with a group of students. Before the trip we had talked about it in class—how long it was, why it was built, the dynasties that expanded it.
But once we were actually climbing it, the conversation changed.
One student looked out across the mountains where the wall disappeared into the distance and said, “Mr. Voss… they built this without machines?”
At that moment, the lesson wasn’t just history anymore. The scale, the effort, and the reality of it all became something they could feel, not just memorize.
Learning about a culture in a classroom is helpful. But sharing a meal, navigating a market, or hearing another language spoken all around you creates a deeper connection.
Travel is experiential learning at its best which is why educational travel and immersive cultural experiences can be so powerful. It invites us to move beyond observation and into participation.
People Remember How They Felt, Not What They Checked Off
Students rarely remember every detail from a lesson. What they remember are the moments that made them feel something: curiosity, surprise, excitement, or connection.
Travel works the same way.
The best trips aren’t defined by how many things you checked off a list. They’re defined by how the experience made you feel.
Maybe it was the moment you watched the sunset in a place you’d only seen in photos. Maybe it was a conversation that changed how you saw the world. Maybe it was simply the feeling of stepping outside your normal routine and realizing how big the world really is.
For me, it’s often the simple conversations that stay with me.
Talking with locals about everyday things—family, work, children, life. The kinds of conversations that remind you how much people around the world actually have in common.
I remember one moment while in Tiananmen Square in Beijing, China, chatting with a family while their young daughter played nearby. I handed her a small sticker I had brought from the United States, and suddenly we felt connected—even though we spoke very little of the same language.
Moments like that make the world feel smaller.
Not because places are the same, but because you start to see the human connections that exist everywhere.
Those are the moments that stay with you.
A Few Questions Before Your Next Trip
Just like in a classroom, meaningful experiences often begin with good questions. Before your next trip, it might be worth pausing to ask a few of your own:
- What kind of experiences do you want to have?
- What perspectives are you curious to explore?
- Where might you go to challenge your assumptions about the world?
- What kind of memories do you hope to create?
Planning a Trip with Purpose
Travel isn’t just about where you go. It’s about what you discover along the way
This is the conversation I have with every client before we build a single itinerary. Understanding what someone hopes to feel, learn, or carry home from a trip is what separates a well-planned vacation from a genuinely meaningful one.
The world has an incredible number of stories waiting to be experienced.
The question is simple: which one will you explore next?
If you’re starting to think about your next trip and want help designing something meaningful, thoughtful, and memorable, I’d love to help you start the conversation.
