Travel Women We Love: Geraldine Ree

Writing a profile on Geraldine Ree after our conversation had me stumped; I must’ve tried coming at it half a dozen different ways, none of which felt like truly I’d captured her.

And then I realized the likely reason for my struggle was because I’d done the interview captivated by her insights – she was the teacher and I her eager-to-learn student. I have a feeling she has this effect on many in the industry.

Ree’s breakthrough into travel came by, quite literally, chasing down an opportunity.

“I was a flight attendant for Canadian Airlines for two years while I was going to university, but my dad really encouraged me to get my business degree, and not to stay on with the airline. I went and got my degree, but I always wanted to go back into travel.

I had my resume on my car seat. I was doing sales calls in Victoria, and I was applying for every airline, Ward Air being one of them, and all of a sudden, this Ward Air car drove past me. I chased them down and said to the sales rep ‘you’re going to think this is crazy, but I think it’s serendipitous’ and I gave her my resume. She told her boss it was worth looking at and that’s how I got into the travel industry.”

Ree’s career in the travel industry is defined by a series of intentional leaps.  Each transition was guided by a single question: Where can I learn more, and where can I make a bigger impact?

“Very intentionally, I didn’t ever want to repeat the same experience twice, because I’m a lifelong learner,” she told us. “And I started in, the back of the plane, and then I got into the sales side with an airline, and then cruise industry was just catching on, so I made the leap to Princess Cruises.

Best thing that ever happened. I won the lottery.”

Ree would go on to have a 17-year tenure with Princess Cruises, and later into retail leadership with Expedia Cruises, intentionally avoided repeating the same experience twice.

Today, as a respected business coach, she is helping a new wave of travel professionals—many of them women—step confidently into leadership.

“In its simplest terms, I help travel entrepreneurs understand how to get their business to run so they can lead.”

Early on, she recalls a stark imbalance: women dominated frontline roles, yet leadership positions were overwhelmingly held by men. The contrast was clear and limiting.

“I remember being at the ACTA awards and it was all women in the room. All the people who did the bookings were the women, but the people on the stage running the industry were men. And I remember thinking, that is really strange. That is such an inverse.”

Ree says today that landscape has shifted. As the industry has evolved, particularly with the growth of independent travel advisors, more women have stepped into ownership and leadership roles. Many did so organically, turning expertise and passion into entrepreneurial ventures.

Ree says however, despite the advancement of women in leadership roles, many still suffer from imposter syndrome.

“Our male counterparts are raised to take more risks, that’s part of the gender. How many times were women growing up told ‘who does she think she is?’ Women don’t want to express themselves on social media because they don’t want to be boastful or seen as having an ego. There’s a lot of ‘I’m not enough, or ‘I’m not too much’.

Ree says it’s important for both women (and men) to switch that mind frame and realize that holding themselves small and playing a smaller game isn’t giving full service to the people they want to serve.

“Right now the industry is just desperate for leadership. There are so many new advisors coming into the industry that women are rightly stepping in and saying, ‘I can help these people and they need leadership, and I need to stop holding myself small so that I can be in a place to really help others’.

I think it’s really improving, and it’s an evolution of where we’re coming from.

But for anyone, my general advice is don’t wait. Ready is better than perfect. If you’ve got the inclination to do something, it’s so important you move on those instincts now.”