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FunTimes Magazine

Diedre McLeod: Solo Travel Coach Empowers Caribbean Women to Explore the World

May 07, 2021 05:20PM ● By Candice Stewart
diedre mcleod solo travel coach

Diedre McLeod, Solo Travel Coach

Traveling solo, especially during a pandemic, appears only as a fantasy for many who will never experience it due to anxiety and fear of the unknown.

However, for one Jamaican woman, Diedre McLeod, she uses these often crippling feelings to fuel her drive for exploring the world.

McLeod’s main focus is to empower people, especially Caribbean women, to take the leap and travel. She does this by sharing her often funny and interesting cultural experiences, encouraging the implementation of safety practices, and showcasing travel hacks and tips on the know-how of preparing for and actually traveling. 

Diedre Terracotta House, Colombia

Besides being a solo travel coach, McLeod is the ““bilingual and adventurous WanderWisher” behind the blog “Diedre in Wanderland”. She also hosts the Instagram (IG) Live Series Stories from Wanderland, where she shares her travel experiences with her audience. 

In one of those stories, Diedre talks about the time she had to hitchhike in India, in the middle of the night, in an unknown location (to her), to get to the airport to catch her flight. She was alone and could hardly communicate effectively with the locals. 

McLeod also had her phone stolen while she was in a cafe in Puerto Rico. She now jokes about how it happened, and the crazy journey she went on to resecure her stolen property. She also shared the story of the time she was stuck in New York because of the COVID-19 lockdown. During that time, her visa expired, and she found herself communicating with officials to try to sort her travel documents to prevent any trouble. There was also a time where McLeod almost got in some trouble with the law in Colombia

Diedre in Treasure Beach, Jamaica

In recalling a moment of foreshadowing, McLeod tells FunTimes Magazine, “I knew when I was a child that I wanted to travel. I was about ten when I told my mom that I wanted a job that allowed me to travel and  that I wanted to learn six languages.” 

English is her first language, and she speaks Patwa (patois), which is also identified as Jamaican Creole by many linguists. She is also versed in Spanish and French and is currently learning Korean - well on her way to 6 languages.

Although as a child she spoke of a life of traveling, McLeod realized as an adult that it is her true calling.

“I resigned from my last regular 9-5 job as a Project Specialist in International Development in Jamaica to teach English in France. It was around that time, upon reflection, that I realized I had left three other jobs before  deciding to go traveling. That’s when I gave in and embraced the solo travel life because it was clearly intended for me,” she tells FunTimes Magazine

She ended up living in France for 5 years teaching English and obtained a master’s degree in corporate strategy and international management.  

Diedre sitting in a Rickshaw in India

McLeod says she has always wanted to travel the world with friends, but life continues to happen where they often pull out for various reasons, leaving her as the last woman standing. 

“Undeterred by unavoidable situations, I always opt to travel alone, and in doing so, I have unlocked parts of me that I never knew existed, and it has afforded me many opportunities in the travel community. It has also exposed me to new cultures and interesting people. This is why I aim to empower women to do the same. As many women as possible should go out there and see the world,” she says. 

“Of course I have my doubts and my fears, but I don’t allow them to cripple me into being stuck in one geographical location my entire life,” she continues. 

Diedre taking a dip in the Blue Lagoon in Iceland


Diedre in Reykjavic, Iceland

 Over the years, she has also lived in Colombia, where she taught French and English, lived and worked in India for about 6 months, where she worked in business development, and traveled to other countries, unlocking newer versions of herself, experiencing new cultures, and meeting new people. 

A few of the other places she has visited include Spain, Kuwait, Iceland, Venezuela, and the Bahamas.

“Solo travel is exhilarating, but it can also stir a melting pot of emotions. I don’t allow those emotions to consume me. Instead, I use it to explore my travel persona, fight through challenges, and make decisions that impact my life on my own terms. That’s the thrill of it all,” she explains.

“When you return home, you’ll find that so many things or people have changed, but in reality, it’s you who changed because of the experiences you’ve had while on your solo journeys. It is somewhat intangible, but you notice that your world view has changed and your opinions expand because of the cultures you get exposed to and the people you meet,” she continues.

Diedre at Las Cuevas del Indio, Puerto Rico

 In late 2020, McLeod used her desire to empower women in solo travel to draft plans to develop a solo travel starter course for current solo travelers and those who want to start. This came when she returned to Jamaica after being stuck in New York due to the pandemic.

As a test run, she hosted a virtual session in February to provide travel hacks while taking pointers to finalize and revamp the content for the course. There is currently a waiting list and anyone  can sign up if it interests them.

Diedre by the Eiffel Tower in Paris, France


The Solo Travel Starter Course is an A-Z roadmap for women who want to safely and affordably travel the world solo by creating epic moments.The course features the basic steps that McLeod has taken on her solo travel journey. It boasts COVID-19 travel advice, video lessons, live coaching sessions, a solo travel planner, and help in finding flights, food, and fun, among other amazing features.

“One of the main reasons I started my Solo travel starter course was because I know many back out of travel plans once they become the only person available for a group trip and due to the fear of doing it alone. I find, however, that the fear comes from lack of knowledge. As such, my course will be perfect,” she shares.

With knowledge comes lessons learned. As such, McLeod shares a few tips while travelling solo. Check them out below!

Major Lessons Learned While Solo Traveling

  1. Solo travel allows you to design your life.
    “It has empowered me and taught me that I am capable of choosing the life that I want to live. It has taught me that I have all the answers if I pay closer attention and take the time to understand.”

  2. There’s more to you than you know.
    “The everyday life of not exploring allows you to do so much and no more. But solo travel allows for many opportunities to unlock versions of yourself that you never realised existed. Your world-view will change once you engage with other cultures and peoples. As a result of that, you will become more tolerant, more understanding, and eager to learn more about other countries and cultures.”

  3. People are more good than they are bad.
    “People are kind, but we are often dissuaded by  the stories we hear of one bad experience. We often don’t give people a chance.” 

  4. Document your travels as much as possible. 
    “It is always nice to look at old travel pictures, rewatch a video from a travel experience, or read from a travel journal.”

Diedre at the Taj Mahal, India


As a voice for travel safety, McLeod was one of the travel safety contributors for World Nomads, who offers travel insurance for Caribbean people. The company is one of the largest travel insurance companies in the world. 

McLeod shares a few safety tips (physical tips and those for peace of mind) below! 

Safety Tips for Solo Travel

  1. Know where you’re going before you head there. 
    “Learn a bit about the culture, the local weather, geography, and prepare your itinerary with targeted activities before getting there. This way, your confidence level goes up a few notches while exploring an unfamiliar place.”

  2. Walk with notarized copies of your important travel Identification and documents.
    You don’t want to run the risk of losing your passport and visas in a foreign country.

  3. Use pen and paper.
    Write addresses, contact numbers, and important names in a book, because your phone or other electronic device can fail you. Let’s not be stuck trying to figure out your next move with a 1% charge on your phone. 

  4. Never disclose details about where you’re staying with a stranger. 
    If they ask you if you are travelling alone, lie. Give the impression that you are travelling with friends, even when you are not. 

  5. Put a ring on it.
    To reduce the chances of unsolicited advances, wear a ring on your engagement finger to discourage people from approaching you in such a manner.

  6. Walk with a 'COVID safe' travel kit.
    Pack it with hand sanitizer, disinfecting wipes, gloves, masks, a portable thermometer, soap, a few ziplock bags, and a bigger compressible bag to store dirty clothes or masks.

  7. Bring medications with you.
    If you have medications to take regularly, travel with those. Travel with allergy medicine as well.

 Candice Stewart is a Jamaican content writer specializing in human interest feature stories. She is a web content writer, blogger, and budding podcaster. 

She holds an MA in Communication for Social and Behaviour Change and a BSc. in Psychology from the University of the West Indies (UWI, Mona).

Follow her blog at, where she shares stories and life lessons through real-life experiences.