Breaking Barriers: Women Chart New Waters in the Sailing Industry

For decades, the world of charter sailing has carried the weight of tradition. At the docks and in the boardrooms, men were almost always at the helm. In recent years, however, the winds have begun to shift. More women are stepping into leadership roles, proving that strength at sea can look many different ways. These women are not only navigating the waters but reshaping the very culture of sailing.

One company at the heart of this change is Waypoints Yacht Charters, a boutique charter company where women are steering both vessels and vision. Among them is Waypoints President Kirstie Palmer Tippett, a leader whose own path—starting at the very bottom and working her way up—embodies both resilience and reinvention in the industry.

A Different Touch at the Helm

Kirstie has been in just about every corner of the sailing world, from scrubbing boats to navigating corporate leadership. Along the way, she’s seen firsthand what women bring to the table. 

“The female brings a difference in customer and owner service, a little more boutique – just brings a different approach, a little more delicate,” Kirstie said. 

It’s a subtle shift, but one that matters. Kirstie is known for treating every boat like it’s her own, a detail that sums up her meticulous and whole-hearted approach to management. 

Kirstie manages yachts worth millions of dollars, but her focus isn’t on dollar signs. It’s on people – the owners and her team.

“I want to be accessible to customers, owners, and staff,” she said. “Here, you’re not just part of a corporate company. You’re part of a family.”

In an industry where scale can easily overshadow service, this kind of accessibility makes a real difference.

Headwinds That Still Remain

Despite advances in recent years, social progress is rarely smooth sailing. For women in the industry, old biases linger. 

“The biggest thing is that everybody will turn to the boys before they turn to the girls,” Kirstie notes. 

That reality has shaped her advice to younger women: “Come with the mentality that we are not daft, we can do it.”

Importantly, she doesn’t see this shift as a matter of men versus women. While Kirstie is passionate about the role of women in the industry, she does not want to understate the value of the men on her team. 

“We still need the boys,” Kirstie said. “Bringing the women into the industry as well, it’s bringing equal opportunity to everybody.”

Kirstie’s vision is largely about balance and creating an industry where women and men are seen as equally capable. Sailing has always been male-dominated, but it is entering a new era. Each season makes it more obvious that women are in the industry to stay.

Mentorship as a Compass

Ask Kirstie what’s most important, and she’ll point not to the boats but to the people. 

“I am a big advocate of mentoring. I love to mentor people, men or women,” she said. “If we can continue to mentor and bring females into this industry, it does everything to raise this industry as well.”

Kirstie sees the charter business as wide open with possibilities, and her own team keeps her inspired to keep chasing new opportunities. The cycle of learning and lifting others up mirrors her own early experiences. 

From the beginning, Kirstie was inspired to work from the bottom up. In the early days of her career, one pivotal and life-changing opportunity to do just that came thanks to Peter Twist of Conch Charters.

“He walked into an office and said, ‘Is there anyone here who would like to do the invoices and do owner statements?’ I was willing to stand up and say, ‘I’ll learn that,’” Kirstie recalled. 

That willingness to say yes—to take on new tasks and risk mistakes—is something she still carries with her today. 

“Don’t be scared to get yourself involved within your team and make mistakes. You learn, and you get better. Never be scared of making mistakes. We may not be correct all the time, but we are going to strive to get better,” Kirstie said. 

The Horizon Ahead

Looking forward, Kirstie is optimistic but clear-eyed. More women continue to step into leadership roles throughout the sailing industry each year. These women, however, continue to face age-old challenges like salary inequality. 

For Kirstie, overcoming these issues – and reshaping the cultural mentalities that go along with them – means staying persistent and resilient.

“Stepping into a man’s world, you have to stand up for yourself,” she said. 

With years of experience behind her, she knows she can do just that. She is committed to helping other women realize the same strength within themselves.

Waypoints and the Personal Touch

That confidence carries over into Waypoints itself. Waypoints is a small boutique charter company, and it prides itself on being hands-on. The company is dedicated to making sure people get the best out of their vacations, and it achieves this by being completely approachable.

It’s a philosophy that stands out. In a charter market where corporate expansion often swallows up individuality, Waypoints is determined to keep its scale—and its heart—intact.

That, perhaps, is the most telling sign of the changes happening across the sailing industry. Women aren’t simply finding their way in; they’re altering its course. Women are bringing new priorities: mentorship, attention to detail, and a commitment to personalized service.

The winds of change are steady now, and leaders like Kirstie aren’t just catching them. They’re steering the ship toward a more inclusive, balanced, and human-centered horizon for charter sailing.

Click here to learn more about Waypoints Yacht Charters.

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