Today we’d like to introduce you to Diana O’Gilvie
Hi Diana, please kick things off for us with an introduction to yourself and your story.
My story starts in Kingston, Jamaica, where I was born and raised. I grew up with a strong sense of culture, curiosity, and storytelling. That foundation shaped everything,my love of writing, my interest in media, and eventually, my career in communications and filmmaking. After earning degrees in English and Videography, I spent years building a diverse portfolio that spanned travel journalism and telling stories that connect the African Diaspora.
It wasn’t until I created Urban Sass Travels that things really clicked. I wanted a space where I could be fully myself, smart, irreverent, travel-obsessed, and deeply rooted in culture. I didn’t see many travel platforms speaking to Black women with nuance and depth, especially ones who were traveling solo, reclaiming their joy, and connecting with ancestral heritage. So I built it.
Urbansass.io is the last iteration of two blogs I created over the last 15 years. I started blogging to document my travel experiences and life as a flight attendant. I did destination guides and planned itineraries. Then, I started specializing in the Caribbean and West Africa. It grew into a storytelling platform centered on what I call “soulful travel”, cultural immersion, food, history, and identity. Over time, it became a space where I could speak honestly about everything from navigating colorism in Latin America to finding peace in a remote beach town. It’s raw, it’s personal, and it’s real.
That voice led to new opportunities, writing for major outlets, speaking on travel and diaspora culture, and producing content that connects people across borders. I now balance that work with my career in public communications, but Urban Sass Travels remains my creative heartbeat. It’s where I tell the stories I want to see in the world.
The journey hasn’t been linear, but it’s been authentic. I followed my curiosity, trusted my voice, and stayed true to my roots, and that’s what got me here.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It hasn’t been a smooth road, but I think that’s part of what makes the story worth telling. Building something like Urban Sass Travels while managing a full-time career in communications has required a constant balancing act. There were moments when I questioned whether my voice mattered in a travel space that often felt very filtered and very white. I had to carve out space where there wasn’t much representation, and that came with its own set of challenges like imposter syndrome, limited access, and sometimes just plain old fatigue.
One of the biggest struggles was staying motivated when the growth felt slow. When you’re creating content that’s personal, culturally specific, and sometimes challenging to mainstream narratives, it takes longer to build an audience. There were times when I poured my heart into a piece and it barely got any traction, while lighter, less nuanced content would blow up elsewhere. That was hard. I’ve had to face criticism that my content was “too Black” or “too African focused.”
On a personal level, traveling as a solo Black woman isn’t always easy either. I’ve dealt with everything from language barriers to microaggressions to navigating places where people like me are rarely seen. But those experiences also deepened my storytelling. They gave me a clearer sense of why Urban Sass Travels needed to exist, not just as a travel blog but as a reflection of what it means to move through the world with both courage and curiosity.
The struggles sharpened my focus and forced me to get clear on my purpose. I’m proud of how far I’ve come, but I never want to sugarcoat the path. It took resilience, creativity, and a whole lot of patience.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I’m a writer, producer, filmmaker and communications strategist, but at my core, I’m a storyteller. Whether I’m leading public campaigns in my day job or creating content for Urban Sass Travels, my goal is always the same, tell stories that reflect truth, amplify culture, and connect people across borders and connect the dots across the African Diaspora.
It’s not just about travel for me and collecting stamps in my passport. It’s about identity, immersing in culture, history, food, art, and how we, especially as Black women, find belonging in unfamiliar places. My work explores everything from reconnecting with ancestral roots in West Africa to solo traveling through South East Asia, Latin America as a Jamaican woman navigating race, class, and language. Readers come to Urban Sass Travels for authenticity. It’s rooted in my lived experience.
I think what sets me apart is my perspective. I see the world through a global lens, and I’m not afraid to ask hard questions or tell the uncomfortable truths.
What was your favorite childhood memory?
I’ve been thinking about my grandmother, Ruby, a lot lately. She made the best Christmas cakes with fruit soaked with rum. Yes, as kids, we ate up those rum-soaked cakes. When she made the batter, she would hand me the wooden spoon and I licked it clean while my little sisters shared the bowl, each dipping their fingers and scraping up the batter with their little fingers. The sweet taste to Jamaican rum cakes is one of my most visceral memories and I miss my grandmother’s cooking very much.
Contact Info:
- Website: https://urbansass.io/
- Instagram: https://www.instagram.com/urbansasstravels/?hl=en
- Facebook: https://www.facebook.com/UrbanSassTravel
- LinkedIn: https://www.linkedin.com/in/diana-o-gilvie-a8705770/
- Youtube: https://www.youtube.com/@UrbanSassTravels
Image Credits
Photo Credit: Diana O’Gilvie and The Eye of Addo
