She gets to race all the bucket-list races – every year. Cruise around tropical Caribbean island. She owns a 45 foot sailing yacht which she brings onboard people from all over the world to join her racing – often finishing on the podium. And she has built a business around a dream lifestyle.
Katy Campbell is the founder of Sea to Sky Sailing and runs a unique “pay-to-play” racing program. It’s a model that opens doors, giving sailors access to world-class racing and real career paths at sea – but also comes with responsibility.
In this episode of the Gybe Set Sailor Stories Podcast, Katy talks about the upsides and downsides. She reveals the behind-the-scenes challenges, the ambitions and dreams, safety priorities, and the rewarding aspects of her lifestyle.
Tune in for a conversation that’s equal parts business and pleasure. Filled with funny (and frankly quite often very relatable) anecdotes and scary moments. Exploring what it really takes to work professionally in sail racing – and what it means to build a life of joy, fulfilment, salt, sweat, and a 45-foot race boat.
Chapters
00:00 Introduction and Background
03:33 Sailing Experience and Career Path
05:22 The Sea to Sky Sailing Business
07:09 Racing vs. Cruising is a Balancing Act
07:41 The Van Isle 360 Race: Challenges and Community
11:20 Building a Competitive Sailing Business
17:17 Navigating Challenges in Professional Sailing
28:25 The Importance of Skills and Certifications
32:42 Safety First: The Role of Training in Sailing
34:33 Joining the Race: Requirements and Realities
40:06 Balancing Business and Inclusivity in Sailing
42:22 Empowering Local Youth in Sailing
46:32 Future of Sailing: Leadership and Inclusion
The Reality Behind the Racing
In Antigua, ahead of her fifth Caribbean 600, the day starts not with coffee, but with race prep and boat work. A backstay adjustment, a safety check, a quiet mental list of what could go wrong – and how to prevent it.
As a racing skipper, Katy manages risk, finances, logistics, and people, often all at once. This is the reality of being both skipper and entrepreneur. Every decision carries weight. Not just for performance, but for safety. Because on this race boat, no one is a passenger. Everyone is part of the crew.
“There’s a legal and moral responsibility,” she explains. “People are paying you to keep them safe.”
That means knowing when to push – and when to walk away. Like the time she pulled out of a regatta due to a keel issue, choosing a month in the boatyard over a potentially dangerous start line.
In this world, money becomes secondary. “You have to treat it as renewable,” she says. But trust? That’s priceless.
Building People Through Racing Programs
Despite the pressure, it’s the human side that keeps Katy going. Life on board strips away small talk and brings people together fast. In a space where conditions are tough and emotions run high, something shifts. Confidence grows and limits expand.
Through her program, she’s not just training sailors. She’s launching careers. Young crew members step on board with ambition and leave with experience, skills, and a pathway into professional sailing.
She’s also committed to creating access, particularly for local Caribbean youth. In a region where global racing fleets arrive each season, she saw a gap and chose to act. By blending international crews with local sailors, she’s building teams that are not only competitive, but culturally richer.
Because in the end, this isn’t just about racing. It’s about creating opportunities, shaping people, and redefining what a life at sea can look like.
And maybe that’s the real dream? Not just sailing fast, but building something that lasts.
Follow Sea to Sky Sailing at:
www.seatoskysailing.com and instagram.com/seatoskysailing
