For years, my friends kept saying the same thing: “You should get into travel planning—you’re so good at it.” And they weren’t wrong. I’ve organized everything from long weekends in Jamaica to full-blown spring vacations in London and Paris. But even though I loved it, I was hesitant. The idea of leaving my stable accounting job to become an entrepreneur felt risky.
That started to change during the pandemic.
I launched a small business consulting firm—almost by accident. And once I saw I could navigate unfamiliar waters and actually thrive, that travel business idea didn’t seem so out of reach anymore.
The final push came after a trip I’ll never forget… for all the wrong reasons.
When a Dream Trip Goes South
I’d spent over two years researching the perfect Caribbean festival getaway for me and my friends. We finally landed on Barbados Crop Over 2022 and booked with a travel concierge company. We joined Zoom meetings, signed up for payment plans, and built up the hype.
But once we arrived, everything unraveled.
From missing tickets and unplanned out-of-pocket expenses to included meals we never got, the experience was a mess. Even worse, the company had no representative on the island. Less than halfway through the trip, I somehow became the unofficial group leader—communicating with vendors, sorting out costume issues, and handling logistics for the company’s other clients.
At one point, I had to step in when the costume vendor refused to hand over outfits due to unpaid balances—something the concierge company never mentioned. It was chaos. And the worst part? No one got reimbursed, despite promises made.
But here’s the twist: that trip also changed everything for me.
Turning Disaster Into Destiny
Despite the disappointment, I walked away with something powerful: clarity. I knew I could do it better—way better. I’d already built strong relationships with Barbados vendors, proven I could lead under pressure, and tapped into my skills in planning, organizing, and problem-solving.
So, I combined all of that with my love for travel and launched Caribbean Island Festivals—a concierge travel company built on trust, transparency, and unforgettable island experiences.
And yes, I’ll be back at Crop Over—this time on my terms.
