By Diona Young
March marks Women’s History Month, a global celebration of the achievements, leadership, and impact of women around the world. In sailing, it’s also a moment to pause and recognize the growing community of women who are shaping the sport in powerful ways.
As a woman working in the sailing industry, one of the most inspiring things I see every day is the number of incredible women stepping into leadership roles on the water. They are captains, instructors, adventurers, business owners, racers, and mentors. They are navigating oceans, teaching new sailors, building sailing communities, and helping others discover the confidence that comes from taking the helm.
What makes this community so special is the diversity of the journeys that lead women to sailing. Some grew up on boats, some discovered it later in life, and others stumbled into it through curiosity or a desire for adventure. But once the wind fills the sails, something shifts. Confidence grows, friendships form, and the water becomes a place where people discover what they’re capable of.
To celebrate Women’s History Month, we asked several remarkable women from across the sailing world to share their stories. Their answers reflect the humor, resilience, confidence, and camaraderie that make sailing such a powerful force in their lives.
Here’s what they had to say.
Kim Walther: Sailing Instructor | National Women’s Sailing Association
What first got you into sailing?
Sailing has always been part of my life. I don’t remember ever not sailing.
I learned to swim and snorkel from a sailboat while island-hopping before I could even walk. My parents cruised the Bahamas every summer when I was growing up, and we sailed every school holiday.
I wrote my first sailing article for Sailing World when I was seven years old. In college I raced on the University of Florida sailing team, and later worked summers in Maine on Windjammers to build sea time for my 100-ton captain’s license by the time I was 21.
Talking about getting into sailing is like talking about getting into breathing.
Sailing is life.
Who are the women who inspired you along the way?
Thirty years ago Captain Maura Hendry hired me at St. Augustine Sailing. She trusted me, and through that trust I gained knowledge and experience teaching students how to operate sailing vessels.
Now we also have a female owner at St. Augustine Sailing, RoseAnn Points, who actively promotes women in sailing. I’ve also found an incredible community through the National Women’s Sailing Association, where I recently joined the board and am building a community specifically for women sailing instructors.
Students, teammates, and fellow sailors inspire me constantly by pushing their limits and supporting each other.
What does a supportive sailing environment look like to you?
Open communication, mutual respect, and trust among crew members.
Everyone should feel comfortable asking questions, contributing ideas, and offering help. Mentors who share knowledge are essential, but so is the willingness to be coached and learn.
Recognition, encouragement, and inclusivity ensure everyone feels welcome and able to participate fully.
What do you wish more women knew before stepping aboard?
Sailing isn’t about strength. It’s about smarts, repetition, and practice.
You don’t have to master everything at once. Learn one skill at a time, then stack them together.
What advice would you give a woman curious about sailing?
It’s normal to be nervous at the beginning. Everyone starts somewhere.
Show up, stay curious, ask questions, and sail with as many people and on as many boats as you can. Confidence grows faster than you think.
Chrystal Young: Owner, LTD Sailing School and the Grenada Sailing Club
What first got you into sailing?
After I got divorced, I had a newfound freedom. Nothing says “freedom” more than sailing. I signed up for a weekend course at the local junior college. Once the engines turned off and the wind filled the sails, I was hooked.
What’s something about this industry that might surprise people?
People think sailing is expensive. And it certainly can be, but it doesn’t have to be. I didn’t have a boat, so I joined a couple of sailing groups in Seattle and ended up sailing about three times a week. I’d help people clean their boat, bring great snacks (not just a bag of chips), and great beer. I kept getting invited back again and again.
Also, have the right gear and keep it to a minimum.
What’s a small moment on a boat you’ll never forget?
We had just finished a disastrous five-day delivery of a 40-foot monohull from St. Croix to St. Vincent. The boat was falling apart the entire way. It was just Chris (the captain and my partner) and myself onboard.
We limped onto a mooring ball in Bequia at 6 am with the jib torn in half and the main ripped. We were still in our foulies, trying to tidy up before anyone noticed the carnage.
Three guys pulled up in a dinghy and asked if we needed help.
“No, we’re ok now, thanks.”
Then one of them asked, “Well, the ladies want to know if you will ever sail with him again.”
I said, “Me? I wouldn’t think of sailing with anyone else.”
What’s your ideal day on the water?
Partly cloudy Caribbean sky, about 80 degrees, wind 10–15 knots, calm seas, and good company.
What’s something you no longer feel the need to prove?
You can be a pirate and still be a lady.
Lisa Batchelor Frailey: Owner Sail Solomans, Master Instructor, ASA Author
What first got you into sailing?
I grew up in a powerboating family on the northern Chesapeake Bay, but when I was about twelve, we got a sailing dinghy.
It was seat-of-the-pants learning, but I loved the freedom that boat gave me. I’d disappear for hours at a time just sailing.
Later I started sailing bigger boats in college, added formal instruction, and I’ve never stopped learning since.
What do you love most about working in the sailing industry?
Every student and client is there for adventure. And I get to help make that happen.
Whether I’m training sailors or helping someone plan a charter, it’s incredibly gratifying to watch people develop the skills and confidence to go on their own sailing journeys.
How does your perspective as a woman shape your work?
After working in male-dominated fields most of my career, I’ve learned to pay attention to how people learn.
Every student processes information differently. Being open and adaptable as an instructor allows me to tailor teaching methods so each person can succeed.
What keeps you excited about sailing year after year?
I worried that turning a passion into a career might dull it, but thankfully it hasn’t.
Sailing is constantly evolving. New boats, new technology, new techniques, new places to explore. There’s always something new to learn.
What’s something you always bring onboard that isn’t sailing-related?
Books, music, cards or dice for entertainment.
Also an inflatable travel pillow and a quick-dry Turkish towel.
Boat yoga is real.
Behan Gifford: Circumnavigator & Cruising Coach
What first got you into sailing?
My father had unrealized sailing dreams, and that made me want to love sailing.
Teaching myself to sail a Sunfish on Lake Huron as a teenager set the hook. It dug in deeper when I accidentally became a competitive dinghy sailor in college.
But the final turn came when my boyfriend — now husband and circumnavigation partner — showed me how sailing could fulfill my wanderlust.
When have you felt most confident on the water?
Confidence comes from competence, and competence grows over time.
Sailing around the world double-handed requires an astonishing range of skills. But the moments when my partner Jamie and I are working in perfect flow together — that’s when I feel most confident.
What’s a lesson you learned the hard way?
The first year of cruising can break you.
We prepared carefully, but I still faced moments where I wondered whether we were cut out for this life. That doubt can feel lonely.
But you keep showing up. You keep learning.
Eighteen years later, I think the ending of that story speaks for itself.
When did you realize your voice mattered?
A woman once emailed me to say she discovered our cruising story while in the hospital battling a life-threatening illness.
She said our story gave her hope for a future with her family. Later she wrote again — this time from her own cruising boat.
That moment reminded me how powerful stories can be.
What excites you about the future of sailing?
Accessibility.
Sailing used to feel like an old boys’ club. That’s changing. More people are discovering sailing, and with it, empathy, responsibility, and connection with the world.
That gives me a lot of hope.
Nikki Henderson: Professional Offshore Skipper
What does sailing give you that nothing else does?
I feel more connected with myself when I’m at sea than anywhere else in the world.
More alive. More me.
I think it’s the freedom.
What has sailing taught you about yourself?
When things get uncomfortable or dangerous — when I really need it — I have an almost endless well of optimism.
What is the sailing world getting right for women right now?
One simple but meaningful change: clothing companies are finally offering real ranges of technical gear designed for women.
What do you hope improves in the future?
A shift in sailing culture.
The language we use, the jokes we tell, the safety standards we uphold — those things shape how welcoming the sport feels.
Even something as simple as saying helmsperson instead of helmsman makes sailing feel more inclusive.
Captain Kira Maxiner: 100-Ton USCG Master Captain, American Sailing Master Instructor
What first got you into sailing?
When I moved to San Francisco in 2013, I knew I would either become a surfer or a sailor. When I learned how cold the water is in Northern California, I hopped aboard a J/88 and never looked back.
When I later learned that only around 7–12% of USCG merchant mariners are women, I leaned in (or leaned out!) and committed to earning my 100-ton Master Captain’s license.
What skill or mindset do you rely on when things get challenging?
When things get challenging on the water, I remind myself that “slow is pro.”
On a sailboat, things can go sideways fast and compound quickly. If you slow down, examine the situation, and tackle it step by step, you gain clarity and confidence in what to do next.
What does sailing give you that nothing else does?
Sailing helped me find my self-confidence and develop leadership skills both on and off the water.
It also gave me an adventurous and supportive community that’s hard to find anywhere else. I love being outdoors, and sailing connects me to the elements and nature in a way that life on land never quite can.
What does being a woman in sailing mean to you personally?
To me, being a woman in sailing means helping lead the way for women on the water everywhere.
There is a place for everyone on a sailboat regardless of skill level, gender, or physical strength. When we work together, share knowledge, and have fun along the way, we’ll cross the finish line together.
Your favorite “I’ve got this” moment?
Some of my favorite moments come a few days into a delivery, class, or offshore passage.
Once the crew has adjusted to the motion of the boat, trust in the vessel builds, and everyone settles into their routines, I know we’re going to get from point A to point B safely.
Many trips start with an ugly uphill bash that makes me wonder what I’ve gotten myself into. It can feel like the hardest thing in the world.
But every single time, we push through the adjustment period. The skies clear, the sails settle, and the crew finds its rhythm.
I look around at the crew that gathered because they wanted this experience. Then I look at myself and remember that I chose this life too.
And in that moment I know:
“I’ve got this.”
Grace Lockhart: American Sailing Instructor, licensed USCG captain
What first got you into sailing?
I grew up in a sailing family and spent my summers racing and coaching through my club’s junior sailing program.
After college, a friend and I completed the Great Loop and I later worked as a sailing captain teaching others to sail.
Now I have a desk job, but I spend as much time as possible racing and getting back out on the water.
What skill or mindset do you rely on most when things get challenging?
When things get exciting, I trust my instincts and rely on my preparation.
Don’t hit anything. Don’t get hurt.
Sailing gives me peace and connection to nature, but racing keeps my competitive edge sharp and motivates me to stay strong and healthy.
What does being a woman in sailing mean to you personally?
Being a woman in sailing is one of my favorite ways to inspire others.
I’ve had incredible adventures, built a career around the water, and competed at a high level.
And sailing is one of the few sports where the playing field between genders can be remarkably level.
What’s your favorite “I’ve got this” moment?
Med-mooring a 52-foot Jeanneau to a concrete dock in a 20-knot crosswind in a tight space.
No fouled prop.
Stuck the landing.
Rose Ann Points: a sailor, educator, yacht broker, and business owner
What first got you into sailing?
Sailing was never my dream. It was my husband’s.
We had a powerboat in the Pacific Northwest, and I was the one who always got seasick. So when he came home one day and said, “We’re selling the house, buying a sailboat, and traveling the world,” my first thought was not excitement.
It was, Oh no.
But I’ve always been an adventurer at heart. I wanted my children to believe they could step beyond comfort and into possibility.
We sold everything, bought a sailboat named Tranquility, and started learning.
One night anchored in the Marquesas, under a full moon with the water glowing in phosphorescence, I stood alone on deck and realized I had a choice.
To resist this life.
Or to fully live it.
That moment changed everything.
What might surprise people about the sailing industry?
People see the romance of sailing — sunsets and open water.
But behind it is responsibility, preparation, and leadership.
And sometimes the hardest part is believing you are enough.
A small moment you’ll never forget
One afternoon my children and I gathered coconuts and returned to the boat. My daughter proudly announced she had baked a carrot cake.
We didn’t have carrots. Or powdered sugar. Or most of the ingredients. She had substituted everything using a notebook of baking swaps.
When my son took a bite he asked, “Why is it crunchy?”
Without missing a beat she said, “If you don’t like it, don’t eat it.”
He replied, “I am eating it. I’m just giving commentary.”
We all laughed.
And we all ate the cake.
What’s your ideal day on the water?
Simply sailing with my husband.
Warm air. Gentle wind. Water like glass.
And the peace of being exactly where I’m meant to be.
What do you no longer feel the need to prove?
I no longer feel the need to prove that I can do everything.
Strength comes from knowing where you shine, where you are still growing, and trusting others to shine beside you.
The Future of Sailing
The sailing world is changing.
More women are stepping into leadership roles as instructors, captains, offshore racers, cruising mentors, and sailing school owners. They are not just participating in sailing — they are shaping its culture.
What stands out across all these stories is not just skill or experience.
It’s community.
Mentors who open doors. Crews who support each other. Families who chase adventure together. And sailors who share their stories so someone else can imagine themselves doing the same.
Every woman who takes the helm expands what sailing looks like for the next generation.
Women’s History Month reminds us that progress doesn’t come from a single moment. It comes from thousands of small ones — the first time someone steps aboard, the first time they trust their instincts in a tough maneuver, the first time they realize they belong on the water.
The ocean doesn’t care who you are.
It simply rewards curiosity, teamwork, preparation, and courage.
And as these sailors remind us, the future of sailing is stronger, richer, and more inspiring when more women are at the helm.
Here’s to the women who sail, the women who teach, the women who explore, and the women who are just beginning their journey.
The wind is waiting.
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