How One Sail Influenced My Future

When Captain Kira Maixner first stepped onto a sailboat in San Francisco Bay, she couldn’t have known that moment would alter her life’s trajectory. Caught between the grind of a tech startup and the weight of post-travel blues, she found in sailing a sense of freedom and resilience that the corporate world couldn’t match. What started as a single evening sail soon blossomed into a career dedicated to empowering others (especially women) to claim their place on the water. Kira’s story is a reminder to all boaters that sometimes, the smallest leaps of curiosity can open the door to a lifetime of discovery, connection, and purpose.

How One Sail Influenced My Future
By Captain Kira Maixner, San Francisco Bay, CA

Ten years ago, I stepped onto a J/88 sailboat for the first time. I didn’t realize that moment would chart the entire course of my future. At the time, I was working in a tech startup in San Francisco, caught between the grind of the city and post world-travel blues. I took a chance on a new boat owner that I met at a crew list party and went sailing one summer evening after work. That first sail (thrilling, humbling, and wildly exhilarating) was the spark that ignited my career on the water.

Kira with her first J/88 Team in 2018 preparing for the Rolex Big Boat series in San Francisco, CA. 

From that sail forward, sailing became the center of my professional and personal life. It wasn't long before I was taking lessons, racing weekly, and spending every spare minute exploring the San Francisco Bay by boat. The water offered something the tech and corporate world couldn’t: a place where skill and resilience mattered more than titles or screens.

Early on, I noticed that there were few women on the water, especially in leadership roles. The few female captains and racers I met left a lasting impression on me—they were tough and inspiring. I realized that if I wanted to pursue this life on the water, I could not only find a place for myself, but also help create pathways for more women to step aboard and take the helm.

Kira instructing one of her very first women’s sailing courses.

Driven by that vision, I earned my Master and OUPV USCG Licenses’ and became an American Sailing Association certified sailing instructor and Master Instructor. I helped launch a women’s sailing program at the local club and it took off. I loved instructing and even more, I felt a connection to a greater something, community, when I taught women-only sailing courses. I began specializing in creating welcoming spaces where they could build confidence, learn to sail well, and see themselves as leaders on the water - just as I had. Over the years, I've had the privilege of certifying dozens of women and mentoring countless others, from first-time sailors to seasoned racers.

Kira holds her first OUPV USCG license in January of 2017

My career today is a direct reflection of that first leap onto a race boat. It taught me that stepping into the unknown with courage and curiosity can lead to a life you would never expect. Sailing has given me freedom, purpose, and a powerful community—and through my work, I strive to pass that gift on to every woman who dares to set sail.

Kira and crew aboard “Chinook” a competitive all women’s race team lead by Elizabeth Henderson

How to Get Involved in Women’s Sailing Events

Women’s Sailing Week with Captain Kira and Stacy Carter aboard a luxury catamaran in the USVI. 

Whether you’re dreaming of rounding race marks or cruising to remote anchorages, there are so many ways to dive deeper into the sailing community — especially as a woman looking to connect, learn, and thrive.

• Learn all that you can, from everyone you can.
  Being new to sailing can feel daunting, but it’s the perfect time to be a sponge. Taking a beginner class at a sailing school and striking up conversations with more experienced sailors is the best way to learn and set yourself up for future opportunities. Stay curious, ask questions, and say "yes" when invited aboard. All good sailors know that every day on the water will teach you something new.
• Attend a presentation by a professional sailor at your local yacht club.
  Many yacht clubs host speaking events featuring professional racers, full time cruisers, and industry leaders. These presentations are full of real-world advice, and often open to the public. It's a great way to meet others and inspire your sailing dreams.
• Attend Women's Sailing Seminars and Classes at local yacht clubs.
  Women's sailing seminars are a fantastic way to sharpen your skills and gain confidence on the water. Topics can range from beginning sailing lessons, docking techniques to race strategy to offshore cruising prep. Oftentimes these seminars are created and presented by women in the local community.
• Join an all-women’s sailing class at the local sailing school or club.
  If you’re looking to build skills in a quick, comfortable, encouraging setting, find an all-women’s sailing course. Some schools offer women-specific learn-to-sail or advanced courses, where you can practice boat handling, sail trim, and navigation with your peers.
• Build your own crew list.
  One of the best ways to get out on the water regularly is to create your own sailing network. Connect with friends, friends of friends, and new contacts who own boats or are looking for crew. Start a group chat, plan casual sails, and make sailing part of your social life.
• Lean into the community — join a yacht club or community sailing center.
  Becoming a member of a yacht club or local sailing center can open hatches you didn’t even know existed. You’ll meet a diverse community of sailors, have access to races and cruising opportunities. You might even find a mentor eager to share their knowledge. Networking at various clubs often leads to lifelong friendships.
• Volunteer at local sailing events.
  Many regattas and boating clubs rely on volunteers to help things run smoothly. Volunteering is a fantastic way to meet active sailors, learn the behind-the-scenes of various events, and get invited aboard your next ride.
• Join a club that offers charters
  Look for clubs that offer affordable charters, fleet access, or social calendars. These clubs often organize casual races, group sails, and themed parties — perfect opportunities to meet new people, get more sea time, and find your tribe.
  
• Attend an all-women’s sailing retreat — like the ones I host in the Caribbean and beyond!
  Sailing retreats are a magical way to immerse yourself in the lifestyle. During these retreats, you’ll sharpen your sailing skills, explore stunning destinations, and bond with an incredible group of women who share your love of the sea. Plus, it’s a well-deserved break from everyday life — and an unforgettable adventure.

About the Author: Captain Kira is a USCG 100-Ton Master, ASA Instructor, offshore racer, and delivery captain with over 50K nautical miles of cruising, racing, and instructional experience. Passionate about empowering women in sailing, she leads women's sailing weeks, all female courses and coaches all-women racing teams through her platform, CaptainKira.com. Whether teaching high-level ASA courses, delivering yachts offshore, or fostering inclusive sailing communities, Kira is dedicated to getting more people—especially women—confidently on the water.

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