When I was about ten years old, my father had returned to the states and bought a small 18 foot wooden sailboat which he launched onto Lake Michigan in Chicago. I cut my early sailing teeth with several short sailing trips aboard “Sunrise.” Decades later, I find myself exploring the Pacific Northwest looking at sailboats and considering the possibility of a life at sea, a thought that has drifted in and out of the tides of my consciousness over the years.
My sailing days expanded later in my youth when my father bought a 22′ sloop in Key Largo, Florida which he named Karma. He later upgraded to a larger 35′ ketch (also named Karma) which became his primary home over the next 20+ years. I took many holidays during my school years to sail with him and my step-mother Sandra. We had journeys in the Florida Keys, the Bahamas, the US and British Virgin Islands, Jamaica, Hispaniola, and lastly Culebra, an Island belonging to Puerto Rico where they settled for many years before moving to Thailand. I loved those sailing times. Though money was never plentiful, good times, banana bread and beautiful anchorages always were.
Sailing as a possible way of life appeals to me for many reasons. I especially appreciate the freedom it provides, the living by one’s capacities, the technical knowhow and practical troubleshooting required to fit and maintain the vessel, the ease of spending time in remote and beautiful places, and of course the actual sailing under power of wind.
I’m writing this, not because I have firm plans to go to sea, but rather to document the early stages should this come to fruition. I’m writing too about the importance of change and the ways in which we can manifest new directions in life. As I’ve allowed myself to freely dream of living new possibilities, I find this movement towards a life at sea accelerating. It feels important for the path to fully choose me rather than the other way around. Like any major life change, I’d like sailing to feel like it becomes a calling I say “yes” to rather than a decision more impulsively made. Yet I’d be lying if I didn’t acknowledge the excitement I have at the possibilities before me.
I’ve been visiting used bookstores most everywhere I go lately and have spent considerable time reading a small trove of sailing books I’ve been collecting.
I also walk docks to study boats, talking with any sailor patient enough to share some of their wisdom and perhaps offer me a tour of their vessel. I feel hungry for knowledge and devour all I can. Recently I completed an American Sailing Association sailing class, living for a week aboard a Jeanneau 451 with three other students, tending the sails and navigating through the beautiful San Juan Islands in Washington and picking up three different sailing certifications along the way. Aside from learning a ton to add to my experience from my younger years, I gained more confidence and most importantly I rediscovered how happy I can be while sailing. Suddenly noticeable was the ease which which I laughed. The combination of the freedom of moving under wind power, the technical aspects of the sailing itself, and spending time in remarkably beauty just seemed to feed and ease my soul.
Looking back on those early sailing days with my father, I can recall that same ease. Memories of snorkeling the British Virgin Islands, dropping hook in a secluded cove in the turquoise waters of the Bahamas, diving off the deck and swimming ashore, meeting fellow live-aboard cruisers, and night sailing past the breathing sounds of sleeping whales along the coast of the Dominican Republic still resonate. Of course there were challenges, but these challenges were also early and formative lessons for me into the value of freedom and living one’s life on one’s own terms, circumscribed only by the bounds of one’s own courage and capacities. There is a price to be paid for true freedom, but the reward is nearly always worth far more than the cost.
My father’s passing less than a year ago has made this exploration a little bittersweet. While it feels important to me that this be my personal journey, I’ve often wished I could call him up and chat through things like what makes a boat well designed for ocean-crossing journeys, the advantages he found sailing a ketch compared to other designs, or even basic questions such as strategies for anchoring in different situations. I got teary while wandering a boatyard in Port Townsend, WA this summer wishing he could be walking along with me and sharing his wisdom.
On the other hand, his passing may actually be making room for these possibilities. When our parents die, we become our own person in ways previously not possible. Autonomy previously struggled for is naturally bequeathed. This decision, given my father’s previous sailing life seems to require my autonomy. To get a boat also feels like it would be an honoring of him, a passing of a baton (or batten in sailing parlance). Although subtle, perhaps the strongest underlying drive toward navigating the seas on my own boat is the vision I have of taking some of his cremated remains and returning them to the sea where he felt most at home. It feels like an important honoring, and also a sense of personal closure since Covid quarantine rules in Thailand precluded my ability to travel to his funeral in a timely manner. On my last visit to Thailand in the year before he passed, he told me that he had let go of his dream of being the oldest man to circumnavigate the globe. The possibility of circumnavigating is the thing that gets me the most excited about sailing. It’s that vision, with visits to small atolls in distant seas, the challenges of lengthy ocean passages, and the endless opportunities yet unknown to me for growth and change that is fueling this acceleration. At a recent bookstore stop, I even bought a copy of “Migrant Cruising Notes Micronesia” just to keep on-hand for inspiration. Tangible tokens of the future can be very helpful in nudging us forward over time.
So much appeals to me about sailing possibilities, yet significant life change is almost always one giant leap which can involve thousands of smaller steps and stages. My father used to like to say that “the hardest part of any voyage is casting off the dock lines.” That applies to most all major changes in life, not just maritime. We can plan and prepare for decades yet never take that critical step of actually doing it. It takes true commitment and courage to step into the unknown. Starting something new takes courage. Almost always, the ending of that which we’ve known and found familiar and comfortable takes even more.
I’ve learned that one of the best ways to tell if I am on the right path is how easy my life energy flows in that particular direction. When inner resistance consistently arises, it’s likely that I am not on the right path. Lately, I feel actual excitement in my body and find I am eagerly leaning into learning as much as I can about boats and sailing. I’ve experienced this before in designing and building my own home, immersing myself in the learning required to complete the project successfully. I’ve also done the same with the design and conversion of my van (my second home). I enjoy larger projects, especially if they involve the creation of infrastructure towards a better life. While I am certain I wouldn’t build my own boat from scratch, I get excited about the learning and effort which would be required to transform a boat into one outfitted specifically for more significant ocean cruising.
We never quite know who we’ll be in the future and how our lives will unfold. The life I have today and the person I have become were beyond my imagination when I was younger. And with any luck, who I will become in the future will be virtually unrecognizable to the person I am now. So today I am playing with the charting of a new course. Perhaps one day I’ll cast off the dock lines of the life I know so well, and unfurl sails towards the one I know not of.