What happens when two friends with a shared passion for travel, purpose, and impact join forces? In this candid conversation, founder Simon Armstrong and director Callum Reilly reflect on the humble beginnings, key challenges, and defining moments that turned CAS Trips from a bold idea into an internationally recognized student travel organization.
Founding CAS Trips
Can you take us back to the moment when the idea for CAS Trips was born? What inspired you to start this journey?
Simon: I started out in sports journalism in the UK, but after two years covering football, I realized it wasn’t quite the dream job I’d imagined. I wanted to travel, so I got my ESL qualification and spent several years teaching English abroad. That eventually led me to teaching at international schools in Indonesia and Switzerland, where I saw firsthand how transformative the CAS program could be—when done well.
What if we brought CAS to life through travel?
Back then, CAS was often treated as an afterthought. Students were overloaded with academics, and schools struggled to make CAS meaningful. Meanwhile, many of the school trips I was organizing felt like empty tourism – fun, but lacking depth. That’s when it clicked: What if we brought CAS to life through travel? Real, hands-on experiences that connected students to communities and gave them space to reflect.
We piloted our first program in Prague with a few schools I knew, and it worked. The students loved it, and I saw the impact immediately. Soon after, I decided to go all in and scale the idea. That’s when Cal came on board, and things really took off.
Callum: I’d say my passion for experiential learning started when I was 16 and spent six weeks on a trip to China. It was a life-changing experience that pushed me out of my comfort zone and planted the seed for studying and working abroad.
It reminded me of how transformative travel had been for me as a young person.
After university, I went into investment banking, but I quickly realized that world wasn’t for me. I was drawn back to travel, exploration, and meeting people from around the world. I moved to Prague, where I worked in short-term tourism, running half-day trips and having a blast diving into the local culture. Simon and I had been friends for a while, and once I got the hang of things, I felt ready to sink my teeth into something more demanding, challenging, and rewarding. When he started growing CAS Trips, it reminded me of how transformative travel had been for me as a young person. It felt like the perfect opportunity to build something meaningful together.
Simon: Yes, the timing was perfect! Cal officially joined in 2015 as we expanded to new destinations. In addition to launching trips in Edinburgh, Krakow, and Berlin, one of his first big projects was the Prague Spring program — which was a logistical challenge but also a defining moment in our growth. Looking back, it was a serendipitous partnership—we were growing rapidly, schools were eager to expand their travel opportunities, and we were ready to take CAS Trips global.
The Power of Partnership and Team Culture
How has your friendship influenced the way you built and shaped the company?
Simon: We’ve always been great friends first and business partners second. Our dynamic works because we have complementary skill sets—there’s no ego, and we’re always aligned in making decisions that are best for CAS Trips. If you sit in on any of our business conversations, they often spin off into tangents about travel, our family and social lives, or community impact strategy, but that’s part of the magic. I tend to be the big-picture dreamer, the creative mind always coming up with new ideas, while Callum is the structured, pragmatic one who ensures everything runs smoothly. We balance each other out perfectly.
We genuinely have fun working together, even through the toughest challenges.
Callum: Exactly. Simon is always thinking about the next step, the next destination, the next way we can innovate. I come in with the practical, operational mindset, making sure the numbers add up and that our plans are executable. That balance has been key to our success. Beyond that, we genuinely have fun working together, even through the toughest challenges. Whether it was growing the company rapidly, working insane hours, or navigating COVID, we’ve always managed to keep a sense of humor. I think that energy carries over to the whole team.
Simon: Yes, that is key. We’ve built a team culture that reflects that energy—everyone genuinely cares about the mission and about each other. From the start, we’ve sought out team members who are travelers at heart, engaged with global communities, and passionate about crafting these experiences for students. It’s evolved to become truly familial over the years.
Challenges and Defining Moments
Were there pivotal moments that made you realize CAS Trips could become something big?
Simon: In the beginning, there were definitely a few moments when we felt we were way over our heads. That said, we always rose to the occasion, and our belief in what we were doing only grew stronger! One of our biggest points of pride is how we handled COVID-19. Overnight, we had to cancel all trips and pivot our entire business online. Instead of shutting down, we doubled down on our mission.
We launched Virtual CAS Conferences, tackling global issues like the climate crisis, equality, and mental health. We brought in keynote speakers, ran breakout sessions, and even created hands-on challenges where students worked on real-world problems faced by charities. That initiative not only kept us going but also deepened our impact. We were able to showcase our educational expertise and draw on the collective strengths of our team. Many of the schools that joined those conferences are still with us today. And through it all, we kept our full-time staff—we never let go of anyone.
Callum: Yeah, that is a huge point of pride for us. Another moment that stands out is when we first started expanding internationally. We were essentially following tour guides around in new cities, waiting until their tours ended so we could grab a coffee and pitch them our idea. Fast forward to today, and we’ve now run trips to 37 destinations worldwide, plus our flagship Global Student Exchanges.
Simon: Yes, the Global Student Exchanges are another thing we are so proud of! Those exchanges truly embody the kind of global citizenship we’re trying to cultivate—they bring together students from different backgrounds to learn from each other in ways that no other program does.
What were some of the biggest challenges you faced in the beginning, and how did you overcome them?
Simon: Growth is always a challenge—scaling while maintaining quality and impact. In the early days, we were running trips while also handling logistics, sales, and program development. It was exhausting, but we were fueled by our belief in what we were building. Over time, we built an incredible team, and that’s made all the difference.
Callum: One specific challenge early on was streamlining our operations. For example, we didn’t have fixed trip dates at first—schools could request nearly any timeframe—which quickly became a scheduling nightmare. Coordinating guides, venues, and transport across a shifting calendar was almost impossible. Another headache was food orders. We used to offer way too many meal options, which led to chaotic spreadsheets and kitchen mix-ups. Over the years, we’ve refined those systems—fixed trip windows, simplified menus—and things now run far more smoothly. But getting there involved a lot of trial and error.
Bringing the IB to Life
The IB’s CAS program is at the heart of what you do. How do you ensure your trips truly reflect its spirit?
Simon: The key is making Service engaging and meaningful. Too often, school trips approach Service as something passive—students are marched into a soup kitchen for a few hours and then leave. We focus on making Service fun, interactive, and community-driven. Our approach is to partner with grassroots organizations that are already doing incredible work and create experiences where students can genuinely contribute. That makes the learning process more impactful and long-lasting.
We focus on making Service fun, interactive, and community-driven.
We pride ourselves on creating experiences that are both meaningful for the students and beneficial for the local communities. It’s the combination of fun and impact. We want students to have an amazing time, but we also want them to walk away inspired. The goal is for them to see themselves as global citizens who can make a difference. Our service projects are designed to be mutually beneficial—not just an exercise in charity but real partnerships that create lasting change.
Callum: We also put a lot of emphasis on pre-trip and post-trip activities. A CAS Trip isn’t just five days of travel—it’s a longer journey of learning, reflection, and action. That’s what makes it truly transformative.
What’s Next for CAS Trips?
Where do you see CAS Trips in the next five to ten years? Any big dreams or projects in the pipeline?
Simon: We’re entering a new stage of growth. Our team is expanding, our resources are improving, and we’re looking at how we can make CAS Trips even better for the next generation. We’re at a stage where we can really refine and enhance what we do. One major focus is making CAS Trips more accessible—privilege is very present in the kind of work we do, and we want to find more ways to allow students from all backgrounds to experience the transformative opportunities we offer.
We see school trips as an enormous opportunity to inspire students.
Callum: We also want to keep evolving our model to ensure even deeper engagement. We see school trips as an enormous opportunity to inspire students at a moment when they are hyper-aware and open to new perspectives. We want to continue innovating how we facilitate those connections.
Final Reflections
If you could go back and give your past selves one piece of advice when starting CAS Trips, what would it be?
Callum: There’s a lot to reflect on here, but on a more lighthearted note, I’d say set arrival dates sooner! It took years off my life managing logistics without fixed schedules. Also, food orders—offering students too many choices made life more complicated for everyone!
Simon: Honestly, I’d say just trust the process. The challenges, the long hours, the unexpected pivots—they all led to something truly rewarding. Seeing the impact on students and knowing we’ve played a role in shaping global citizens makes it all worth it.
