Olivia Fleming
Travel Advisor

“Travel isn’t just where I’ve been—it’s in who I’ve become, shaped by a family legacy, driven by curiosity, and carried forward through every experience I create for others.”
Having grown up watching my mom and nana build their careers in the travel industry, I’m excited to now be stepping into this world myself. Travel has always been a part of my life, and this is a new chapter where I get to contribute in my own way while continuing a strong family legacy.
I currently run my own cleaning business, which I’m incredibly proud of. It has taught me independence, discipline, and what it takes to build something from the ground up. I’m excited to balance that with a career in travel—bringing together entrepreneurship and a lifelong passion. Growing up, I was fortunate to travel to incredible destinations including Mexico, Hawaii, Cuba, the Dominican Republic, the Bahamas, and throughout Europe—Switzerland, Germany, Italy, France, and Greece. These experiences shaped my love for travel, culture, and connection.
I studied graphic design, and I love being able to bring a creative edge to the family business. I spend my time curating trips and creating “Hot Deals” for our Vacations for Heroes site, combining both my passion for travel and design. I’ve also enjoyed working on website creation, helping refresh our platforms with a new perspective, and I’m proud to be part of that growth. Personally, I love to travel—especially all-inclusive resorts and cruises—and I’m always looking for new experiences to share with others.
At 24, I’m focused on building a future that allows for both career and family. One of the biggest reasons this industry speaks to me is its flexibility—the ability to work from home, earn additional income, and create a lifestyle that supports raising a family while continuing to explore the world. While I run my own business, I’m excited to be working part-time alongside an amazing group of agents, as well as my mom and twin brother. I’ve seen firsthand how this career can turn a passion for travel into a flexible, fulfilling lifestyle, and I’m excited to continue growing within it.
Call 236-361-3571
My passion for travel
Travel has always been a part of my life, inspired by watching my mom and nana build their careers in the industry. Growing up, I had the opportunity to explore destinations across Mexico, the Caribbean, and Europe, which sparked my love for culture, connection, and new experiences. Now, I’m excited to step into this world myself—continuing a strong family legacy while creating my own path. I’m passionate about curating meaningful trips, especially all-inclusive getaways and cruises, and love combining that with my creative background to help bring travel experiences to life for others.







