How Traveler Diedre McLeod Helps Caribbean Women Solo Travel Comfortably
Photo Credit: Diedre McLeod

Photo Credit: Diedre McLeod

How Traveler Diedre McLeod Helps Caribbean Women Solo Travel Comfortably

black owned business , Jamaica , traveler story
Nasha Smith
Nasha Smith Jul 30, 2021

In the West Indies, the term ‘barrel babies’ refers to kids whose parents migrate overseas — to the United States or the United Kingdom — usually for economic betterment. The name comes from the blue plastic or brown cardboard cylinder used to ship goods back home to the Caribbean to support family members. Diedre McLeod was one of those babies. She started traveling from a young age, visiting her mother in the United States. And now, she’s a solo travel guru.

“I spent most of my summers back and forth traveling by myself, [as an] unaccompanied minor, back in the days,” she recalled. “I think that sparked the interest. When I would go back and forth between the US and Jamaica, I was always interested in culture and the difference between Jamaica and the US. I was usually in New York. So what can I do? See the subway or go to larger museums? I grew up always being really interested in culture, even when I’m not traveling, in the books I’m reading.”

Solo Travel
Courtesy of Diedre McLeod

When McLeod started her corporate job back home in Jamaica, the idea of solo travel as an adult, unattached to visiting family, started appealing to her. She left her job in 2009 and moved to France to teach English, making it her first intentional individual solo trip. While there, McLeod discovered an affinity for slow travel where she could move about various countries unhurried. This lead to a stint in India for six months and another in Colombia for a year. It was quite a departure from the traditional travel habits of West Indian women based on a strong migrant culture rooted in familiarity.

“People move abroad often. This is not shocking to us. But in your everyday circles, people are still afraid of traveling. They’re not going to travel somewhere without a strong network of familiarity. So if there’s no family member where they’re going or they don’t have a close friend, or they’re not going with family or friends, then somehow it becomes this scary prospect.”

McLeod is now a business strategist and travel blogger who goes by the moniker Diedre in Wanderland and provides travel consultations for solo travelers. She shared some tips with Travel Noire for aspiring solo travelers who are still a bit hesitant about taking the plunge into the unknown.

“I think people don’t realize when you group travel, you focus a lot on the group and group dynamics, and you focus on your role in the group. But when you solo travel, you have to make all the decisions by yourself. And sometimes, when you think about it, it might seem daunting or overwhelming, but it’s so empowering. In the end, you’re like, ‘Oh, I didn’t know I could do this.'”

Solo Travel
Courtesy of Diedre McLeod

Solo travel is not that different from other trips

Solo travel is quite similar to all the other types of travel, like group travel. There are lots of commonalities, a lot of similarities. If you’re already willing to take the plunge, then you already have the curiosity. I would say understand what kind of traveler you are first. That will make arriving at your destination or choosing one a lot easier.

Have a plan

Figure out one thing that you want to explore. Don’t try to do everything all at once, because then it’s going to be overwhelming or chaotic, and that’s when you run into problems. This is a new experience, a new way to travel, so just choose one thing. Maybe this trip I want to focus on knowing food in the place, or I want to focus on water adventures, or just visiting museums, or you want to relax. Focus on one reason why you want to travel and then do that.

Take a walking tour

The biggest one which I do immediately is a walking tour. They’re amazing. It’s the best way to get familiar with the location. That’s also a good way to interact with locals because if there’s a guide, or you walk past a friendly storekeeper or something, then you can interact with locals in a relatively relaxed, easygoing way, and get familiar with the area. So the next time when you say, ‘Okay, it’s time for me to go on my adventure,’ then you won’t feel so lost because you start recognizing places.

Be independent

Solo travel, even if you’re staying with family. Don’t rely on them for your itinerary. Leave and do it by yourself. I think this is another thing that Caribbean people do. We’re always waiting for auntie or uncle or whoever you’re staying with. Or you don’t do anything during the week. You wait until the weekend or when the family member has a day off and that’s when you go out. Like no, even if you’re going to stay with your family and your friends, just do things by yourself.

For more tips on solo travel, check out Diedre in Wanderland’s resources and follow her on Instagram.