Hugo Ortega didn’t grow up dreaming of yachts. Raised by Dominican and Honduran immigrants in the Bronx, he followed the blueprint his parents laid out: college, a stable career, and a steady paycheck. But by his mid-20s, despite having “made it” as an engineer, he was burned out and deeply unfulfilled. A spontaneous backpacking trip led him to a chance encounter that changed everything—and launched him on an unconventional path to becoming a Superyacht Captain, entrepreneur, and mentor for a new generation of global explorers.
A Life Rewritten
By 24, Hugo had checked all the boxes. He had a materials engineering degree, a corporate job in Houston, and a long-term relationship. But inside, he was struggling. “I did everything right—and I was miserable,” he recalls.
The engineering office felt like a prison. Every morning, Hugo would sit in traffic for an hour, stare at spreadsheets for eight hours, then sit in traffic again. The work felt meaningless, disconnected from anything that mattered to him. His weekends were spent recovering from the week, not living. “I remember looking at my older colleagues and thinking, ‘Is this it? Is this what the next 40 years look like?’” The thought terrified him.
His parents had sacrificed everything to give him opportunities they never had. They’d worked multiple jobs, saved every penny, and pushed him toward stability and respectability. The idea of walking away from their dream felt like betrayal. But Hugo was drowning in someone else’s definition of success.
When his company faced layoffs, he saw a way out. Hugo quit his job, ended his relationship, and bought a one-way ticket to Southeast Asia. “Everyone thought I’d lost my mind,” he says. “My parents were devastated. My friends said I was throwing my life away. But I knew if I didn’t leave then, I never would.”
The first few weeks of travel were liberating but also terrifying. Hugo had no plan, no safety net, and no idea what came next. He was carrying the weight of disappointing everyone who believed in him while trying to figure out who he actually was beneath all those expectations.
In a hostel in Myanmar, he met a South African deckhand who told him about the Superyacht world: “You don’t need experience. You just need to start.” The guy was tan, relaxed, and most importantly, he seemed genuinely happy.
That conversation changed his life. Hugo returned to the U.S., completed his STCW training, passed his medical exam, and landed his first job crossing the Atlantic on a Superyacht. He hasn’t looked back since.
“That first Atlantic crossing was the hardest thing I’d ever done,” Hugo remembers. “Seasick for three days straight, working 16-hour shifts, questioning every decision that led me there. But when I saw that sunrise over the ocean on day four, when I realized I was actually doing it—I knew I was home.”
Making Yachting Accessible
Ten years later, Hugo is a seasoned Captain and the founder of Superyacht Sunday School, a digital mentorship-based course designed to help people with no experience break into the yachting industry.
“Too many people get scammed by overpriced training that doesn’t actually get them hired,” Hugo says. “I built Superyacht Sunday School to give people a real roadmap—especially those from non-traditional backgrounds.”
The program covers everything from how to write a standout CV and network effectively to preparing for interviews and relocating to yachting hubs like Fort Lauderdale or Antibes. It’s hands-on, personal, and community-driven.
“I didn’t grow up around boats, and I didn’t have any connections,” he says. “Now I help people like me get their foot in the door—and land the job.”
More Than Boats and Beaches
One of the biggest misconceptions about the industry is that it’s all glamour and parties. “Social media has romanticized yachting,” Hugo says. “The truth is—it’s a job. A hard one. But the rewards are insane if you’re willing to work.”
Entry-level crew can make $3,000–$4,000/month with no expenses. Add charter tips, and the earnings can double or triple. More importantly, crew get to live rent-free, travel the world, and build financial freedom.
But the financial benefits are just the beginning. “When you’re working traditional jobs, you’re trading time for money in someone else’s dream,” Hugo explains. “In yachting, you’re building skills that transfer anywhere—leadership, problem-solving under pressure, cultural intelligence, adaptability. You’re not just earning money; you’re becoming someone new.”
The personal transformation is what Hugo finds most remarkable. “I watch people discover they’re capable of things they never imagined. A server from Ohio learns to navigate by the stars. A hairstylist from Chicago becomes fluent in three languages. A college dropout develops the confidence to lead a team of twelve people across international waters.”
The challenges are real and demanding. Crew work long hours in confined spaces, deal with demanding guests, and navigate complex social dynamics while being far from home. Weather can turn dangerous quickly, equipment fails at the worst moments, and the pressure to maintain perfection is constant. “You learn to handle stress, think on your feet, and work as part of a tight team where everyone’s safety depends on everyone else doing their job right,” Hugo says.
But Hugo stresses it’s about more than money or even personal growth. “Yachting gave me purpose. It gave me confidence. It gave me my life back.” For many crew members, the industry becomes a path to discovering what they’re truly passionate about. Some become marine biologists, others start charter companies, and many use their earnings to fund entrepreneurial ventures or advanced education.
“You’re not just working on boats,” Hugo emphasizes. “You’re learning about yourself, about the world, about what’s possible when you step outside your comfort zone. That’s worth more than any paycheck.”
Success Story at Sea
Hugo’s students come from all walks of life—hairstylists, servers, baristas, and tradespeople. One standout is Miya, a former U.S. hairstylist of 15 years who joined the course while backpacking in Switzerland. With Hugo’s guidance, she relocated, trained, and landed a full-time stew position on a 40-meter yacht bound for the Bahamas.
“She may not have fit the traditional mold,” Hugo says, “but she crushed it because she was determined.”
This kind of transformation is what drives Hugo. “I’ve helped over 200 people land jobs. Every time someone messages me saying, ‘I never thought I could do this’—that’s the win.”
A New Kind of Captain
For Hugo, this moment is full circle. He’s honoring his immigrant roots while empowering a new generation to pursue freedom, adventure, and purpose—on their own terms.
“You don’t need a fancy degree, a boatload of experience, or a trust fund,” he says. “You just need the courage to start.”
Interested in working on a yacht? Start with Hugo’s free 45-minute training here and see if it’s the right fit for you. It could be the beginning of a completely different life.
Hugo Ortega, is a seasoned Superyacht Captain, recruiter, and founder of Superyacht Sunday School (SSS), the online platform dedicated to helping everyday individuals break into the elite world of Superyacht work—no boating experience required. Drawing from his own journey of escaping engineering burnout, Hugo provides a roadmap for aspiring crew members, emphasizing that determination and the right attitude can open the doors to a life of adventure on the high seas.
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