From traveller to Trip Manager: the Contiki Cinderella story

Do you think you’d like to be a professional traveller? Take care of people from across the globe, make new friends everywhere you go, and unlock the joys of the world for hundreds of people every year?

We talked to two of our Trip Managers, Carlen Oliviera and Emily Shepard, about their travel love stories and why they decided to take that relationship to the next level and become a Trip Manager! Find out about their journeys from early travel passions to growing into full-fledged globe-trotters and vacation experts!

Before becoming a Trip Manager, had you always been a passionate traveller?

Emily: “The short answer is yes! I’ve always been a passionate traveller and loved learning about other cultures. Becoming a Trip Manager has really given me a different perspective on travel and the world.”

Carlen: “Yes, although I’m not sure I would have described myself as such. Growing up, my family didn’t set off on big vacations, so how could I be ‘passionate’ if I never left my home country? But my parents showed me that you don’t have to travel abroad to find a love of travel – there’s so much to do and see in your own country before taking on the rest of the world!”

“After the Covid-19 pandemic travel restrictions were lifted, I planned a 3-month backpacking trip around Europe. When I returned home months later, I didn’t feel as drained as I thought I would. To me that was the sign that travelling was a passion of mine, and that travelling for a living was something that wasn’t actually that crazy of an idea.”

Where have you travelled to that you loved the most?

Carlen: “I get asked this question all the time on the road and I have a hard time just picking one location, but I always say that Switzerland just ticks off all my boxes. The views are jaw-dropping and I got to check paragliding off my bucket list.”

Emily: “For me it’s Mongolia. I went with my grandma and together we lived a nomadic lifestyle for almost 3 weeks – this was my first time being out of the United States and my first time being exposed to a whole new culture. It’s what made me fall in love with travel and learning about new cultures. I got to hike the gorgeous Mongolian steppes, watch traditional wrestling tournaments, and help the women milk their herds of yaks.”

What destination is still on your travel bucket list?

Emily: “My goal is to visit all 7 continents before I turn 30 – I am currently at 5 out of 7! So, one of the top locations on my bucket list is Antarctica. I think the wildlife is so unique and the route to get there through Drake’s Passage is a journey in itself. There is so much to learn about that part of the world. In terms of exploring my own country, I’d love to visit Alaska – similar vibes.”

Carlen: “There are so many places that I still want to visit like Hawaii and New Zealand, but I think the Nordic Countries are at the top of my list. I’ve experienced a European summer, and as a Canadian who loves the cold, getting to see places like Norway, Denmark and Sweden in the winter would be something straight out of a fairytale.”

Had you been on a Contiki before becoming a Trip Manager? If so, which one?

Carlen: “I’d been on a few Contikis before I became a Trip Manager! The first one was a week-long trip to Ireland that I booked with one of my best friends from home. The trip was kind of a big deal for me since it was the first time I was travelling abroad without my parents and it’s what kick-started my love for Contiki and social travel.”

“The second I went on was a 3-month backpacking trip around Europe – it was one of the best decisions I ever made. On day one I instantly clicked with a couple of girls I now consider to be my platonic soul mates, I had a whirlwind summer romance, and I got my first tattoo, because when in Rome, right? We danced in the rain through the streets of Florence, swam at sunset on a beach in Nice, and drank wine while watching the Eiffel Tower sparkle until the early hours of the morning. What more could you ask for out of your summer trip?”

Emily: “Yes, I went on a Contiki solo to Scotland and Ireland. I was solo travelling in Europe for 6 months during that time, and I thought that hopping a Contiki in those countries would be the easiest way to reach some of the most remote cities and destinations. It was the best decision I could have made – the group was fantastic, and we visited so many places I’d never been to before! The trip opened up my eyes to the benefits of social travel and I haven’t gone back since.”

What made you want to become a Trip Manager?

Emily: “The Contiki I went on. I loved my Trip Manager, Brooke, and I was so intrigued by the behind the scenes work that Trip Managers do. I was a recent college graduate and was struggling to find a way to start my career, but I loved the idea of interacting with people from all over the world so much.”

“I loved how passionate Brooke was about all the history she knew and how she was able to manage such a large group of people. I actually had a few girls on my trip come up to me and tell me that I would be a good Trip Manager, so that was the push I needed to apply!”

Carlen: “There’s a saying I heard while on a Contiki that made me realise that being a Trip Manager was something I could actually do, and it’s the idea that this role isn’t just a job, it’s a lifestyle.”

“I had just finished my solo backpacking trip and still felt like I wanted to be on the road, hopping from city to city, meeting new people. That was the moment where I realised I might have what it takes to be a Trip Manager, because you really do have to like the idea of living out of a suitcase, constantly being on the go, and also have a big enough social battery to meet new people every couple of weeks.” 

“Since I had been a passenger on a few Contiki’s, I got a taste of what life on the road was like, so I knew that it was a style of travel that I enjoyed and could see myself doing long term. It’s fast paced and action packed, but there’s also quiet moments where you can sit back and take in your surroundings.”

Are there any benefits to being a Trip Manager? 

Carlen: “The idea that you get to say you travel for work is pretty cool, I don’t know how many people get to say that! Aside from all of the beautiful places and activities you get to take part in, even as the Trip Manager you develop friendships with people all over the world.”

“You definitely learn a lot about yourself while on the road and how to handle tough situations – whether that be a scheduling issue or how to find a balance between a handful of different personality types, this job gives you all sorts of new skill sets. Being on the road all the time also gives you a new perspective on life and what you want to get out of it.”

Emily: “The benefits of being a Trip Manager go way beyond the travel experience you get. I’ve built some deep connections with travellers all over the world. I’m a people person so I’ve always enjoyed meeting new people. But this job has helped me grow into the manager and leader I’ve always wanted to be.”

“I get to travel all around my country and show people all the great things the United States has to offer. I take a lot of pride in sharing my country and the different cities we visit. I have now built strong relationships with friends and suppliers in each city.”

What’s your favourite part about being a Trip Manager?

Emily: “My favourite part of being a Trip Manager is definitely the people I meet along the way. From all the travellers that I get to guide to all the people I work with in each city. I get to cross paths with so many people I would have never met before.” 

“Being a Trip Manager is a really unique job that not many people understand. I’ve really relied on other trip managers as my support team and I love connecting with them to share our stories.”

Carlen: “As cheesy as it may sound, it’s getting to watch strangers become family. As someone who got to experience the Contiki bonds first hand, I love getting to be the fly on the wall to see how the group’s dynamic changes from the first day’s timid introductions, to all the teary goodbye’s on the final day. It’s so special to have even the smallest part in helping people connect and build lifelong memories, and I definitely don’t take that for granted.”

What makes you happy and/or proud to do your job?

Carlen: “One of the coolest things about being a Trip Manager for Contiki is that I’ve been able to experience so many amazing sights and activities that make me proud to be Canadian, while also experiencing it through the eyes of a traveller. I find that it’s easy to start to take things for granted, especially when in your own country, but watching people get excited about Canadian culture or shed happy tears when checking something off their bucket list is something that I don’t think I’ll ever get tired of.”

Emily: “I love the impact these trips have on people. I can see when people come out of their shells or share a particular experience that they wouldn’t have at home. I love being able to help people on their first solo travel experience. I can really see how these trips can change people’s lives. For weeks after trips, I love seeing everyone’s photos and videos recapping their experiences. I’m so happy that I get to share my love of travel with everyone that comes on my trips!”