A Talk With Carolyn Ray, Publisher of JourneyWoman

Last year I joined a boatload of SATW member editors on a Crosi Europe river cruise in France and got to drink wine and eat fine meals with Carolyn Ray. She’s the woman overseeing 25 contributors and a lot of moving project parts at JourneyWoman, a solo travel resource for women over 50 and one of the longest-running travel publications on the internet. I got the scoop on her back story and what makes this award-winning publication and company unique. 

 

Before we get to your own history, I believe JourneyWoman goes back to a pre-internet print newsletter in the early 90s. What’s the story of how it started and where it went?

That’s true! JourneyWoman started as a printed newsletter in Canada in 1994, which Evelyn Hannon sold mostly through bookstores. I think it was $20 a year. I have some of the original issues, which are terrific.

In 1997, JourneyWoman went online as one of the world’s first travel websites, and as Evelyn said, that’s when the “female travel revolution” really began. Evelyn was really seen as the world’s first solo travel writer and was actively running JourneyWoman until she passed away in 2019, when I was invited to take it over by her and her family. I had the privilege of sitting with Evelyn in her hospital room just before she died, holding her hand, with her daughters Leslie and Erica, assuring her I would treat JourneyWoman with great care and love, as she had done for 25 years.

I was incredibly intimidated by what she had created—and the huge shoes I had to fill. It has been an enormous learning curve for me, learning about the travel industry, publishing and running this kind of online business.

When you took over the site, you didn’t come from a travel writing background like most bloggers and publishers. What was your career path like and how did that background help?

When I took over JourneyWoman, I had just sold everything I owned to travel and was living in a rented apartment in downtown Toronto. I had just quit my big consulting job, given back my car, and my daughter was off at university. I felt free for the first time in my life. I had a big map on my wall with stickers on all the places I wanted to go, and had dreams of travel writing.

I had been writing (unpaid) for a travel blog out of Italy for a few years. While I had honed my writing in my career, I didn’t understand then the descriptive storytelling nature of travel writing.

I spent most of my 30-year career in communications and marketing, where I learned about building brands from the inside out — and the importance of having a strong sense of purpose and values. At the consulting firm I led in Canada, I learned about research, which has been helpful in the travel market now, as we strive to get recognition for the woman 50+ traveler. All of this helped me evolve JourneyWoman and think differently.

When I took over the publication, I was leading my own consulting firm. I hired our team to modernize JourneyWoman with a new design system and built a brand new website. My whole family, including my daughter, was involved, as was Evelyn’s family, in every step. We did it all together, with a view to sustaining her legacy. It really is still a family business.

To learn about the industry, I reviewed a lot of travel websites to understand how they made money, which is mostly through digital advertising. Frankly, it felt wrong for me. I didn’t want to randomly promote products and services I didn’t know on my beautiful new website. I wanted to stand behind everything on our site through my own experiences or those of the readers. That’s what Evelyn did too.

But that had implications: I had to innovate other ways of creating revenue and funding the editorial, without sacrificing my values. I have always been the type of person who prioritizes purpose over profit, and I felt that the trust we had built over 25 years was a really valuable asset, one I wasn’t prepared to give up just to make money.

Now you have a team of people keeping the wheels turning and a lot of initiatives in the works. What accomplishments or stats are you most proud of?

When I relaunched JourneyWoman in March 2020, it was at the beginning of the pandemic. I had just gone on my first press trip to Cuba. I had hired an editor to help me develop content. I felt this obligation to keep JourneyWoman going because I realized early on that many of our readers were not just solo travelers, they were solo women, and the pandemic created massive isolation and loneliness. We held community calls every week for two and a half years and got through it together.

That’s when I realized that JourneyWoman was much more than a mailing list. It’s as very special community of women who truly care—not just about me or the website but about the world and each other.

I’m proud of a lot, actually. When I get emails or calls from women who have read an article on our website, and feel inspired to travel, that’s a win. When I have a new company join our Women’s Travel Directory, which is a completely unique innovation started by Evelyn 20 years ago, continued by me, I’m thrilled. When I’m invited by a travel company to help them develop a new solo or women-only product because of our research, I’m over the moon.

When I see a need in the market, I ask, “Why not me?” and make it happen. One example is our Women’s Speaker’s Bureau and another is our Awards for Women Over 50. There is no one creating what we’re doing and I love that.

Some people think JourneyWoman is a big business but we’re not. We’re a very small one. We are a scrappy, all-women Canadian team, evolving together. One of our values is to make our own rules, so I get a lot of joy out of watching our team do that, not following the crowd, and not being afraid to be different. I truly don’t know what other websites are doing anymore, I just focus on what’s right for our readers, partners and community.

Today, we have a community and mailing list of about 100,000 women from all over the world, including a private group on Facebook, and very consistent and strong website traffic. Having said that, I’m more focused on quality not quantity, and the opportunity to be influential in a way that benefits women 50+.

What is the role of freelancers for Journeywoman and what do you see in a freelance pitch that makes you want to say yes?

I am the only full-time employee at JourneyWoman, so freelancers are vital for us. The reason I started hiring freelance writers was to represent more diversity, both in age and experiences. We have had an accessible solo travel writer, Tanzila Khan, for 3 years. I have 3 female writers over the age of 80 to represent their perspective. We have about 25 freelance writers now, and I’m very careful about who writes for us.

In a pitch, I am looking for someone who knows JourneyWoman, who has been part of our community in some way. Maybe they knew Evelyn, or joined a community call or webinar. I want people who care about our readers, the issues we face, not just great writers. As a member of SATW and the past chair for the Canadian chapter, I’m also looking for women who are members of accredited travel associations.

This publication is more than an online magazine, with offshoots including tours, retreats, a podcast, a gear shop, and more. What are the biggest revenue buckets for you?

We have three main areas of focus: the first is of course our editorial, which is designed to support the UN’s SDGs, particularly gender equity. This includes our monthly JourneyWoman magazine, a subscription newsletter called “Smitten” with curated recommendations from readers and my own experiences, and ebooks like Never Too Late: How Women 50+ Are Making the Rules, which I co-authored with Lola Akinmade.

Our second area of focus is our Women’s Travel Directory, which is a membership-based directory that supports women-owned businesses, as well as the larger companies, offering tours and retreats for women. We vet and interview every company in our Directory and work with them to create exclusive “Hot Flash” offers for our readers, and build their brands. Our Directory also includes small ships and places to stay recommended by women.

Last year, we announced a major partnership with TourRadar that allows our readers to find and book trips through their technology platform, which now has over 8,000 trips for women, making it the largest resource of its kind in the world. I’m really proud of that; it’s a gamechanger in women’s travel.

In 2024, we launched a consulting business, which provides research on the needs of women 50+ to travel companies and destinations, as well as assistance with branding, product development and marketing.

While we make money on affiliate marketing, the main driver of our business is our Directory, and creating integrated marketing campaigns with our partners to help them grow their businesses. Many of our partners have been with us for 20 years, and say that JourneyWoman helped them get started.

I would like to see our consulting business grow, as I think it’s imperative to have data to create change in the travel industry. We’re piloting some new initiatives, like our new shop and our “Ageless Adventuress” podcast, which is supported by Globus, but many of the things we do are to shift stereotypes about age and ability, not necessarily profit.

You’ve traveled to loads of places the past few years. Which ones did you find to be the most surprising or inspiring?

Right now, I’m travelling to about 20 countries a year, and just spent two months in Malaysia, my 80th country. I am enjoying returning to places I know well, like Spain, but I also enjoy new places like Romania, Cambodia and Vietnam. I am very keen to challenge my western perspective and help me think differently about our world. Asia is perfect for that, as is South Africa, which I visited last year. If we only travel in our comfort zone, we don’t learn about empathy and understanding.

Through my own example, I am focused on helping to break stereotypes about places that are often said to be “unsafe” for women to travel to. Like Mexico, Colombia, Ecuador, Morocco, all of which I’ve been to multiple times. I also want to show women why we travel: not just for the fun of it, but also self-discovery, lifelong learning, and longevity benefits.

If women travel and support women-owned businesses, they can uplift and change communities for the better. That’s the true gift of travel—a real win-win for everyone.

 

Named one of the Most Influential Women in Travel by TravelPulse, Carolyn Ray took over Canadian-based JourneyWoman in 2019 after a successful 25-year career in consulting. An award-winning writer, she leads an editorial team of 25 female writers and published her first book Never Too Late: How Women 50+ Travellers Are Making the Rules in 2025, with co-author Lola Akinmade. In 2025, she published the industry’s first study on the US$519 billion women 50+ travel market, called “Invisible No More: The Ageless Adventuress” and is frequently featured in major media outlets for her insights on women’s solo travel. She is the immediate past chair of the Canadian chapter of SATW, a member of Women Travel Leaders, and a Herald for the Transformational Travel Council (TTC).