5 Minutes With Carolyn Ray of JourneyWoman (Travel Interview)

For McCool Travel’s 200th travel interview, I am pleased to present Carolyn Ray from JourneyWoman. Remember in the previous interview when I said that so many amazing travel content creators call Toronto home? Well, add Carolyn Ray to that list.

Also from Toronto, I have interviewed: Dave and Deb (ThePlanetD), Jennifer Weatherhead Harrington, Nora Dunn, Will TangChristopher Mitchell, and Jane Canapini. Phew!

Anyway, YES, this is my 200th travel interview and I am thrilled that Carolyn agreed to share her thoughts and travel expertise. I have been a long-time fan of JourneyWoman, since the 1990s when Evelyn Hannon founded the brand. Carolyn now owns it and serves as editor.

Carolyn Ray’s bio:

Carolyn Ray is the CEO and Editor of JourneyWoman, the iconic solo travel publication founded in 1994 (by Evelyn Hannon). In 2022, she traveled to 17 countries, spending several months in Mexico and Spain,and is currently seeking new destinations where she can continue to enjoy margaritas, learn Spanish, and live the life of her dreams. She was named one of the most influential women in travel by TravelPulse in March 2023 for her work bringing awareness to the influence of women over 50 in travel.

Founded in 1994, JourneyWoman™ is the world’s first solo female travel resource and one of the most popular and trusted online women’s travel brands in the world. JourneyWoman also operates the world’s largest Women’s Travel Directory, with hundreds of women-friendly tours, retreats, and accommodations to support small tourism businesses around the world.

Carolyn Ray in Oaxaca
Carolyn Ray in Oaxaca

Travel Interview With Carolyn Ray from JourneyWoman


I’m Canadian but I grew up in a small (then) beach town called Stuart, Florida. I was in the marching band and wrote the astrology column for our high school newspaper. Not so cool, but these were two things I absolutely still love today: music and writing. My family didn’t travel – after all, we were in Florida. The only travel we did was driving up I-95 to visit my grandparents in Toronto. Stuart has changed a lot and is now being marketed as a tourism destination, which makes me giggle a little bit.


Most of my travel is for long periods of time, so I tend to bring a lot of boring things that I can carry easily, like one pair of sneakers and layers. I donated most of my clothes five years ago, so I tend to only buy what I need and then recycle clothing. For example, I did a horseback riding trip in the backcountry and had never been on a horse – so I needed boots for sure. The rest, like cowgirl shirts, I got at Value Village and then brought it back so it could be worn again.

I always have:

  • A rubber door stopper, for safety in hotel rooms (yes, even when there is a lock!)
  • A headlamp, for midnight runs to  the outhouse when camping or in the backcountry.
  • My airpods, most museums use apps now so you need headphones, and I love listening to music all the time


Home is Toronto (I came here for university and stayed), but now live in a 500-square foot apartment that I can lock up and leave anytime. Last year, I went to 17 countries, which I don’t recommend. This year, I’m trying to be more practical and spend more time on self-care and taking care of myself.

My top three (as if that’s possible!) are:

  1. Anywhere in Southern Spain, where I spent most of the winter—Malaga, Seville, Cordoba and all the small towns in that area
  2. Key West, because it’s a place where you can be anything, even in a zombie bike parade
  3. Mexico, where I lived for almost five months learning Spanish and falling in love with Mexico’s culture (Oaxaca, Merida, San Miguel de Allende)


I love traveling solo but anytime I can travel with my daughter is the best. I’m a single mom and we’ve traveled together since she was three years old. I love all of our time together, but my favorite memory is when we went to Kenya when she was 15, watching her interact with the girls there, discovering how much they had in common. That trip was a turning point – we came home and decided to sell everything to travel, donated our clothes and were ‘homeless’ in about six weeks. I’ll never forget that feeling of freedom!

JourneyWoman CEO Carolyn Ray and daughter Alyx in Key West
Carolyn Ray and Alyx (daughter) in Key West


So many….

  1. Value Village/ Savers – because I rarely buy anything new anymore and prefer to recycle clothing
  2. I have three well-loved Gregory women’s backpacks, great for the Camino and hiking
  3. I love my Celestron binoculars for star and moon gazing the compact ones for regular outdoor use


In addition to asking other JourneyWoman members for their tips and advice (which we share and publish
every month):

  1. credit card points to book flights (I use the TD Aeroplan credit card)
  2. public transit since I don’t own a car
  3. long stays of a month or more when I travel

(Oh, and I downsized five years ago to travel, so not owning anything helps too)


Because I grew up on the ocean, I love being on the water. Seeing the horizon reminds me of the infinite possibilities available to us, that we can go and be anything we want when we set our minds to it.

  1. find the ocean – anywhere but warmer is better
  2. bring a travel speaker for dancing (I have a JBL Clip that I love)
  3. head to the local market and eat at the counter – no better way to connect with people
JourneyWoman Carolyn Ray at Killarney Dark Sky telescope
Carolyn Ray at Killarney Park Ontario Dark Sky telescope


I didn’t really start traveling until my 40s, and I know that the first step is often the hardest. “Take the first step” – it doesn’t need to be huge. If you want to travel solo, try having dinner with yourself at a restaurant near home. Take a staycation in your city. Work up your confidence before you do a big trip. (Then my next one is “You can do it!“)

OR “you don’t ask, you don’t get”. This is my philosophy with most things – hotel rooms, restaurant tables – you have to ask for what you want. No one is going to give it to you. And by the way, you deserve it.


This question makes me realize I need some new hobbies!

  • Goodreads for book inspiration
  • Airbnb for travel inspiration
  • LinkedIn for inspiration from other women entrepreneurs


My shell necklace from walking the Camino de Santiago in September 2021. This was my first international trip ‘after’ the pandemic and I was practically alone. Many places weren’t open yet in Spain. It feels a bit surreal now, thinking back to it.


In Oaxaca, one of my favorite places to wander… Pork tacos at El Lechoncito de Ora, the best street food in Oaxaca


Astronomy. I’ve been traveling to different Dark Sky Reserves, learning about the planets and our connection to the universe. As Carl Sagan said, we’re made of stuff from stars.


We have a travel book club and I’ve been able to meet several of our featured authors—including Jane Christmas (who wrote the Camino classic “What the Psychic Told the Pilgrim”) when I was in the UK last year, and Laura Maya (author of “Tell Them Your Name,” set in Nepal), when we were both in Dubrovnik.


Angelina Jolie. I admire her authenticity, her ability to strike her own path, and the important work she has done with the UN, long before it was trendy. Like Princess Diana, she’s been out there making a meaningful difference for years.

Carolyn Ray of JourneyWoman wearing denim jacket with wings
Carolyn Ray, JourneyWoman

Thank you so much Carolyn for sharing your travel advice and inspiration.

Follow Carolyn Ray at JourneyWoman and JourneyWoman’s social media channels Facebook, Instagram, YouTube, LinkedIn, and Twitter.

McCool Travel presents tips from travel experts in our 5 Minutes travel interview series—featuring travel industry giants, super frequent travelers, and adventurous persons.

Previous 5 Minutes travel interview: Will Tang

Sharing is caring!