How Lisa-Gaye Shakespeare turned her wanderlust into a thriving global travel business

Lisa-Gaye Shakespeare would watch television for hours, sitting on the mat of her Clarendon home in Jamaica. Beaches, buildings, jungles, and cultures would flash before her nine year old eyes – the tiny box became her window to foreign worlds.

This wanderlust followed her into adulthood, turning into an enviable career as a travel influencer. Lisa’s deep desire to share her experiences motivated her to create the Shakespeare Agency, which partners with tourism brands to provide incredible travel adventures to those with a hunger like nine-year-old Lisa had.

Lisa-Gaye answered our questions on being a travel influencer, the unfortunate timing of starting a travel service during the heights of the COVID pandemic, the importance of re-connecting to Africa, and how she takes care of herself during her many travels.

How long have you been a travel influencer and how long did it take you to find success in the field? 

Lisa-Gaye: Officially, I started to monetize being a travel influencer in 2021, however I’ve always loved traveling, because I strongly believe that you should fill your life with adventures, not things. For me, travel has been the best education I’ve experienced. 

In 2017, I applied (along with over 6,000 people from all over the world) for a role with a travel website that was searching for someone to move to Cancun for six months to create online content and showcase the city. I had to create a video showcasing my own city, which was Miami at the time. Unfortunately, in spite of overwhelming support from my family and friends, I didn’t get past the top 50 applicants. That experience however, re-ignited my fire and passion for creating content and my love for travel.

So, in January 2018, I decided to start Shakespeare Travels, and in late 2019 I left my corporate career to pursue travel as my full-time career. I moved back to Jamaica in the beginning of 2020 to kickstart my newfound travel career, but obviously, the global pandemic hit in early April, which caused a hard halt in my travels. To stay afloat, I had to reshuffle my plans and create an online agency, where I taught dance fitness classes and managed social media for small businesses. I also wrote press releases. This is where the Shakespeare Agency was born.

I never forgot about travel, and even though I could not travel internationally, I took the opportunity to explore Jamaica. I sought out the hidden gems of the island, and cemented my content creation and marketing skills by collaborating with boutique hotels and villas. While I was successful in growing my social media following and gaining momentum online, as I previously mentioned, I did not see any financial success until 2021, when I rebranded my agency to solely focus on travel. 

Now, I am absolutely loving my business. I’m working with top travel brands and sharing my love for travel experiences with over 34K followers on Instagram and hosting group trips around the world.

Why is travel important to you, and why would you encourage other women to do more of it? 

Lisa: Travel is an extraordinary thing. Visiting new places, experiencing different cultures, foods, and adventures can change the way you see yourself, and what you believe is possible for you. My enthusiasm for travel began when I went on a school trip to Cuba. I was twelve years old at the time, and that enthusiasm has only grown over the years. I know that many women are nervous to travel alone, which is why I offer group experiences. I also know that there are women out there who have no idea where to even start, which was part of the reason I started sharing my own travel experiences. I think especially for women of color, knowing that travel is possible and how it can enrich your life is so important. There are a lot of women traveling nowadays who are the first women in their family to do so, especially solo. That’s a big part of why I love to share what I know, and help others to live their travel dreams too!

Has being a Jamaican woman presented any advantages or obstacles throughout your travels? 

Lisa-Gaye: As a Jamaican woman, I have great pride in being from the Caribbean. Representing my island is a big deal when I travel and I love sharing where I come from – especially when I visit Africa, because the welcome that I receive is overwhelmingly beautiful. I remember the first time I visited Ghana using my Jamaican passport and the immigration officer said, “Welcome home, Sister” – I literally teared up. I experienced this several more times while visiting other African countries. Using my Jamaican passport to visit Africa has been golden, as we don’t need a visa for many countries like Ghana, Uganda, Senegal, South Africa and Tanzania, which are all countries I have visited on my Jamaican passport.

Overall, I can’t say that I have ever experienced obstacles being a Jamaican woman while I travel, but I am very conscious that some of my travels have taken me to places where I do not see other people who look like me. When I visited China, it wasn’t the best experience, because I was constantly stared at and had my photo taken without my permission. It was quite uncomfortable, to be honest, but this is also part of the reason I want to help more people of color, and women of color in particular, to travel the world and experience different places – so we’re not seen as an anomaly.

You exude a sense of confidence, health and vibrancy. What are some self care habits that have brought you to this place, and how do you think this helps your work? 

Lisa-Gaye: Self-care when you travel is so important. Basic things like hydration and good nutrition become vital when you are traveling to new places. I am careful to take the best quality skin care products (soap, moisturizers, face cleansers, masks etc.) with me when I travel, as I am never sure what will be offered locally. Knowing that wherever you are in the world you can take care of yourself to your usual standard means you can focus on having a great time. I’m a big fan of massages as well, especially when I’m abroad. Mainly because it’s usually so much more affordable and there’s nothing like an amazing massage when you’ve been on excursions and adventurous activities back-to-back. Also, I strongly believe that the most important part of travel self-care is the right mindset. When we travel, so much of what we do and what happens can be influenced by others, so going in with a positive mindset and being flexible is a total gamechanger. 

As a world traveler, why do you think it’s important for Caribbean people to connect with Africa? 

Lisa-Gaye: I could go on and on about this question, because it’s a subject I’m truly passionate about. As a woman who spent her early life in the Caribbean, and long periods of time based in the US, returning to Africa and reconnecting with cultural experiences, traditional foods, and authentic practices has enriched my life beyond words. The Caribbean has such a wonderful and varied culture, but this is amplified in Africa, and connects us with the roots of who we are. I remember when I first saw ackee (Jamaica’s national fruit) in Ghana, I had that sense of feeling like I was home. Getting to experience the roots of our food, our music, our culture… There’s absolutely nothing like it. The way we dance, the food we eat, our customs and traditions are so similar. That’s because our ancestors were stolen from Africa and brought to the Caribbean during the slave trade. This history is so important for us, especially as Black people whether from the Caribbean or the United States, to learn, feel, walk, be present in, experience and truly understand. Traveling the world is an education, but traveling to the Motherland and taking in everything Africa has to offer is an expansive and rewarding experience.

How do you think Caribbean and African women specifically, can benefit from community building? 

Lisa-Gaye: As I mentioned earlier, there have been times when traveling that I have seen no one that looks like I do. It is quite an uncomfortable and lonely experience. Those times remind me of the importance of a sense of belonging. Building a community of women of color who are traveling the world increases the opportunity for us to feel that sense of belonging, and to enhance our own sense of self and connection to who we are as well. During my travels, I have been blessed to have met some incredible women with whom I bonded on a deep cultural and emotional level, as we exchanged cultures and beliefs, while recognizing our similarities and embracing the differences. One thing I love most about traveling to Africa is attending traditional weddings. I’ve attended three African weddings now (in Egypt, Uganda & Ghana) and they have been some of the most beautiful experiences I’ve had while traveling. The love and support from family is a remarkable sight, which goes to show the importance of community building.

You have accomplished an international career, while living both in Jamaica and the United States which is still highly unusual and trailblazing. What advice would you give other women who dream of establishing that for themselves? 

Lisa-Gaye: The best advice I can offer is simply to follow your passion. As cliche as it might sound, it’s truly the best thing I’ve done for myself. Share what you love, follow your heart, and travel to places that light you up, but don’t be afraid to travel to places you perhaps haven’t considered too. I always knew that I wanted the freedom to travel the world and experience new things, so when the opportunity came to build a business around that, it was an easy yes. It started with sharing my “likkle” island of Jamaica with the world, which evolved into showcasing my travels worldwide. I’m blessed to live this lifestyle and while it’s “unusual and trailblazing” as you said, it’s not impossible. This is why I also encourage more women, and women of color specifically, to not just travel, but to become travel influencers and build businesses around their experiences. So, not only do I share my travels, but I also work directly with women who want to build a career as a travel influencer, mentoring them as they begin their own journey.

What’s next for your career?

Lisa-Gaye: The world is my oyster, and who doesn’t love oysters! The more I travel the world, the more enthusiasm I have for helping others to do the same. The more of us there are sharing the possibilities travel can bring, the better we all will be. That is why my business is always evolving from planning travel for others, to helping other influencers build their businesses, to planning and hosting my own group trips, and working with more brands within the travel and hospitality space. My ultimate goal one day is to have my own travel show. So stay tuned, this little country girl from Clarendon, Jamaica is only getting started!

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