Co-Founder/Tour Operator
Gabriel A. Callaway
Born and raised in San Diego, Gabe Callaway comes from a long line of ocean explorers. As a third-generation waterman, the sea has always been in his blood—a legacy of adventure and respect for the deep.
Gabe built a successful career on land as the owner and operator of one of San Diego’s premier landscape design companies, where he combined creativity with technical expertise to craft stunning outdoor spaces. But no matter how much he shaped the land, the ocean was always calling.
Gabe met his wife, Emily, while surfing the waves of San Diego—an instant connection rooted in their shared love for the sea and adventure. Together, they decided to turn that passion into something greater. In 2025, Gabe and Emily founded Black Flag Scuba, a scuba tour company in Maui, to share their love for the ocean and create unforgettable experiences for those eager to explore the underwater world.
Beyond diving, Gabe thrives on adventure in all forms. Whether surfing, freediving, spearfishing, kickboxing, Jiu-Jitsu, rock climbing, or backpacking, he embraces every challenge with the same energy that fuels his passion for the ocean. Above all, he cherishes time spent with Emily, their daughters Nora and Harper, and their close-knit circle of family and friends.
Continuing his family's legacy of exploration, Gabe is forging a new path—one that leads straight into the depths of discovery.
Co-Founder/Operations
Emily Callaway
For Emily Callaway, the ocean is more than just a place—it’s a way of life. A third-generation San Diegan, she grew up with a deep appreciation for the water, adventure, and the boundless beauty of the natural world. Descended from a long line of fishermen, Emily’s connection to the sea runs deep, instilling in her a natural rhythm with the tides and a lifelong respect for the ocean’s power and mystery.
Her love for the sea was only reinforced when she met her husband, Gabe, while surfing in San Diego—an instant connection that would lead to both a lifelong partnership and a shared dream.
With a strong academic background, Emily earned her degree in International Studies with a Concentration in Global Health from the University of Washington, later earning her Master’s in Public Health from UCLA in 2015. While she thrived in the world of public health, she discovered another passion—entrepreneurship. She became instrumental in the success of GCLA Landscape Design, serving as its Chief Financial Officer (CFO) and Operations Manager, ensuring the company’s continued growth and excellence.
She also launched her own health coaching practice, empowering others to live vibrant, balanced lives by blending modern wellness science with natural, sustainable habits.
But the call of the ocean never faded. In 2025, Emily and Gabe founded Black Flag Scuba, a scuba tour company in Hawaii, to merge their passion for adventure with their desire to share the magic of the sea with others. More than just a business, Black Flag Scuba is a reflection of their love for the ocean, exploration, and the thrill of discovery.
Above all, Emily’s greatest joy is being a mother. She loves raising their daughters, Nora and Harper, with the same adventurous spirit that has shaped her life. Whether she’s diving, surfing, climbing, or simply embracing island life with her family, Emily finds fulfillment in every wave, every dive, and every moment spent exploring the world alongside those she loves.
Together, she and Gabe are charting a new course—one built on passion, family, and the call of the deep.
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Honorary Rescue Diver
Nora Callaway – Honorary Lifeguard, Black Flag Scuba
At just 3 years old, Nora Callaway already lives life with the spirit of a true ocean explorer. As one of the honorary lifeguards at Black Flag Scuba, she proudly represents the next generation of sea lovers—always ready with a big smile and an even bigger sense of adventure.
Nora loves climbing rocks, splashing in the surf, and cruising the beach with her identical twin sister, Harper, by her side. Whether they’re playing in the sand or pretending to lead their own scuba tours, these two are inseparable and always on the move.
With salt in her hair and curiosity in her heart, Nora is already making waves at Black Flag Scuba—one sandy footprint at a time.
Honorary Rescue Diver
Harper Callaway – Honorary Lifeguard, Black Flag Scuba
Harper Callaway, age 3, is the other half of the dynamic twin duo lighting up the shores of Black Flag Scuba. As an honorary lifeguard, Harper brings endless energy, imagination, and a big love for the ocean to the team—always ready for the next beachside adventure.
Harper spends her days surfing tiny waves, climbing rocks, and going on wild seaside missions with her identical twin sister, Nora. The two are inseparable and always dreaming up new ocean adventures, whether they’re building sandcastles or pretending to rescue sea creatures.
With a fearless heart and a big smile, Harper is already proving she's got saltwater in her soul and adventure in her blood.
The Legacy Continues
A Legacy Beneath the Waves
The story of Black Flag Scuba begins generations ago, with my grandfather, a pioneer who started one of the first local scuba businesses in Southern California. His deep respect for the ocean and passion for exploring its mysteries laid the foundation for a family legacy built on saltwater and adventure.
He passed that love down to **his son—my father—**who spent his life diving, exploring, and teaching his five sons not just how to dive, but how to truly appreciate the power, beauty, and serenity of the sea. That passion became a part of me, and now, my wife Emily and I carry it forward through our lives, our work, and most importantly, our children.
Together, Emily and I founded Black Flag Scuba as a tribute to that legacy—a way to share the magic of the ocean with others, just as it was passed down to us. Today, our twin daughters, Nora and Harper, are growing up surrounded by that same spirit of curiosity, adventure, and deep connection to the water.
Black Flag Scuba isn’t just a business—it’s a continuation of a family tradition, a celebration of the sea, and a commitment to nurturing a lifelong love for the ocean in every generation. Through every dive, every tour, and every wave, we honor the legacy that started with one man and continues now through us—and through our daughters.
Contact us
"Get in Touch with Black Flag Scuba – Dive Into Adventure!"
P: 619.729.8040
E: callaway@mauiblackflagscuba.com
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