Meet the Jamaican Teaching Women How to Solo Travel the World

Meet the Jamaican Teaching Women How to Solo Travel the World - Taj Mahal India diedre in wanderland

Diedre McLeod has been travelling by herself for 11 years. It first started when she resigned from her corporate job in Jamaica and moved to France to teach English. “I began to feel suffocated and uninspired by the corporate 9-5 life. I could no longer see the impact of my work, so I left.”, Diedre explains.

The move to France was not without challenges. Diedre almost became homeless, had to quickly adapt to a new culture, learn a foreign language, and try to connect with people from different backgrounds. Despite this, Diedre stands by her decision to move across the world. The positive impact of teaching English to French students, watching them improve their language skills, and being able to share her Jamaican culture made it all worth it.

Las Cuevas del Indio Puerto Rico Diedre in Wanderland

Las Cuevas del Indio, Puerto Rico

While living in France, Diedre would plan trips on the weekends with friends but often ended up postponing because people would back out at the last minute. Frustrated and yearning to explore her new home, Diedre decided to go on the trips by herself anyway.

This newfound freedom to forge her own path, make her own decisions, and travel at her own pace sparked an interest in travelling solo and discovering even more. Since then, Diedre has travelled to more than a dozen countries by herself, and she has lived and worked on 4 continents.

There’s no denying the benefits of solo travel. Travelling alone brings something truly valuable to the table…you’re more likely to meet new people, chat with local, and immerse in the culture. Solo travel allows you to truly practise self-care, be selfish, and spend every day on your vacation the way you want. It’s a confidence boost and it helps you to step out of your comfort zone to try new things.

Treasure Beach Jamaica Diedre in Wanderland

Treasure Beach, Jamaica

“Travelling alone, as a woman, is an empowering gift.”, says Diedre. “I discovered a new side to myself. I found out that I was bolder and more adventurous than I thought. It sounds cliché but travelling alone made me grow into myself.” A study by Hostelworld (the world’s largest hostel booking travel site) shows that solo female travel has increased by 88% over the last four years.

There is usually a mix of shock and intrigue when people find out that most of Diedre’s travels are done solo. Diedre would blog and share her experiences travelling alone around the world. Eventually, more people, especially other Jamaicans and Caribbean women, started to ask questions about how they could travel on their own.

Diedre has since launched her “Solo Travel Starter Course” for women who want to learn how to travel alone. The course teaches you how to solo travel the world fearlessly, using the same 6 steps that Diedre uses to plan her own solo trips.

And if you’re wondering…yes, this includes advice on how to travel alone during the coronavirus pandemic and being covid compliant. Diedre was stuck abroad during the heights of the CoVid19 outbreak in March 2020. She lived through 4 months of strict lockdown in New York City and also had to fly internationally.

All of Diedre’s lessons, trials, and experiences over 11 years of travelling alone are poured into the Solo Travel Starter Course. She also gives 6 weekly travel coaching sessions as part of the course, along with other bonuses.

Reykjavik Iceland Diedre in Wanderland

Reykjavik, Iceland

“I wish I had someone to guide me back when I started solo travelling 11 years ago. So I want to give women the tools to be empowered and feel safe to take trips by themselves. You don’t need to wait on anyone to travel and create your epic life moments.”

For more info on the Solo Travel Starter Course, visit:

Diedre McLeod is a Jamaican travel writer, business strategist, and travel coach. She blogs about her travels at “Diedre in Wanderland” and often hangs out on Instagram @diedreinwanderland to give travel tips.

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