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Meet Kaylie O'Brien: TSC's Newest Entry-Level Mariner Instructor

When I stepped onboard Lady Washington as a Two Weeks Before the Mast participant back in 2012, I was practically floating with excitement but had little idea what to expect. I certainly wasn’t prepared to encounter an industry and way of life that would become both a personal and professional passion.

Kaylie joins the TSC team as the program's Entry-Level Mariner Instructor. Welcome, Kaylie!

Today, I’m thrilled to be the instructor for the Entry Level Mariner class offered by The Seafarer Collective and I can’t wait to meet my first cohort of students. TSC’s mission formalizes the amazing mentorship, training, and professional development opportunities that have existed on tall ships everywhere for decades. It also makes those opportunities more accessible than ever to the next generation of captains, mates, engineers, and onboard educators. As the program enters its second year I look forward to watching how it continues to change the maritime industry for the better.

Growing up in the Northwest, I was fairly oblivious to the region’s maritime history and global presence until I intentionally went looking for it. Even then, I had to do some digging before I found a way to get on the water in a meaningful way! I don’t think I’m unique in that regard, and am proud to be a part of an organization that’s committed to getting similarly interested folks from sea to shining sea working on boats.

During my career as a professional mariner, I’ve witnessed the transformative power of maritime on the individual and vice-versa. I’ve also witnessed a deficit of credentialled mariners in the industry, often due to the complex and sometimes prohibitively expensive application process. The more we can do to help motivated folks from all backgrounds get involved and invested in maritime, the better! I’ve loved working with Hali, Sarah, and the other TSC instructors to put the finishing touches on a class that combines a strong traditional foundation with thoroughly modern skills to prepare its graduates for whatever maritime career path they choose. I know that if TSC had existed when I joined my first vessel, I would have avoided much of the muddling through and hard knocks that made my early forays into the world of licensing tedious. Thankfully I can draw on those experiences to help my future students navigate their own professional courses!

I’m a USCG licensed captain, an experiential educator, and recently began teaching in a middle school while completing my state teaching certification. I also hold degrees in History and Political Science from the University of Idaho. My husband (a fellow mariner who I met while crewing on Hawaiian Chieftain) and I live on the coast of Maine where we’re lucky to have access to the largest fleet of traditionally-rigged vessels in the country. When I’m not sailing, you’ll most likely find me fixing up our home, a schoolhouse built in 1829, and enjoying Maine’s glorious outdoors.

Feel free to reach out to me at

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