This story originally appeared on the Gents Cafe Newsletter. You can subscribe here.
Sailing has perennially been one of mankind’s most evocative and symbolic ventures. Great poets throughout history, including Samuel Taylor Coleridge, Emily Dickinson, Walt Whitman, and countless others have employed sailboats, great seafarers, and voyages as metaphoric representations of the human experience and historical events.
As an adolescent, I always envisaged sailing as an out of reach gentlemanly endeavor. My imagination overcome with images of JFK manning the helm of Manitou in cream slacks, and a bomber jacket with the Presidential Seal on the breast, or the English Royal Family (and later Frank Sinatra) aboard their bespoke vessel, The Southern Cross. In my youthful naivety, sailing seemed to be reserved for people of a certain pedigree. A class of gentlemen I was not born into.
As time marched on and age brought wisdom, I learned that I could not have been more wrong – and all the while paradoxically correct – in my assessment. For the past three years, I have lived aboard my own sailboat, and needless to say, I am not a Kennedy nor in the Royal Family. Yet, through firsthand experience, I can confidently state that sailing is one of the most gentlemanly passions, and not at all for the vain reasons I once associated with it.
When I tell people that I live aboard a sailboat in the Caribbean I am usually met with the same reactions – “Wow, you are living the dream,” “Must be nice,” or more sarcastically “Oh isn’t your life tough.” My reaction would likely be the same if I had never embarked on this unorthodox journey. Yet, pardon the pun, there is more beneath the surface. A type of character that is drawn into sailing and undeterred by its many discomforts and even hardships is what makes a man; a deeper appreciation, thoughtfulness, positive attitude, and persistence despite challenges are what makes a gentleman.
As I delve deeper into this lifestyle, meeting sailors along my journeys and reading about the greats, I find a few things to be true about the sailing community generally:
- It takes a unique devotion to own and maintain a sailboat. These vessels are constantly exposed to the harshest elements and require continuous care – blistering heat and beating sunlight, paired with constant motion and corrosive saltwater, wear down even the best-built boats. A true gentleman sailor does not lazily leave their vessel to be destroyed by the elements: they master their craft as riggers, mechanics, carpenters, electricians, plumbers, and fiberglass experts all in one. After all, when you are on the open sea, there is no mechanic on speed dial to rescue your boat when things break down. Real sailors get their hands dirty and work hard to keep their boats seaworthy.
- Sailors prioritize skills over convenience. As demonstrated above, all boat ownership is work, but those who choose to sail take on even more. Driving a motorboat with an engine and a helm is simple and intuitive – especially in an age where virtually everyone can drive and has access to a car. Learning how to harness the wind is an additional skill appreciated by those who wish to broaden their horizons and go above and beyond. It also comes with the added responsibilities of learning about and maintaining rigging.
- Sailing embodies considerateness in numerous forms. One thing is known to be true among all sailors: you do not sail on a schedule. The wind and the weather may have conflicting plans, and it is not the fastest or most reliable form of travel. Yet, it is environmentally friendly, bypassing the need for heavy fuel consumption and relying predominantly on natural phenomena. Sailing is also economical in that regard, and increasingly sailors become more and more self-sufficient through their use of solar power, wind generators, and desalinators (also known as watermakers). Aboard a well-prepared vessel, you could live many months of complete and total independence without ever requiring the support of society at large.
- Sailors are the archetypal “Gentleman Explorer.” Ernest Shackleton and his exploits aboard the Endurance are the stuff of legend and are still used today as an illustration of leadership. Sir Robin Knox-Johnston and Bernard Moitessier defined the Sunday Times Golden Globe Race in 1968 when they took vastly different approaches (equally noble in their own rights) to single-handed sailing around the world non-stop and without any assistance.
- Lastly, and more stereotypically applicable, sailing can also be incredibly leisurely. Few experiences are more peaceful or absorbing than calmly gliding through the sea with no other sounds to be heard other than those of the wind and the waves. On good weather days, there is nowhere better to be than on the open sea in the company of good friends.
Gents Cafe promotes Slow Living, and sailors embody this mentality in spades. Living in the moment need not negate long-term thinking however, and modern sailors trim their sails perfectly to the shifting winds of the world we inhabit today. Sir Peter Blake exemplified this in his deep love for the sea and sailboat racing, as well as through his enduring efforts to preserve the environment. When you live aboard a boat you intrinsically understand the importance of preservation. If the boat goes down, you do too. The same goes for the world that we inhabit. Life is sweetest when you are attentive to it, and it is difficult to not appreciate life when you are in the middle of vast oceans from which all life is derived.
No, I don’t think of Royal or Presidential Yachts anymore when I think of sailing. Anybody can easily find their way on board a vessel, taking pictures of their Mediterranean holiday or for publicity. Instead, I think of the cramped spaces I need to wiggle into so that I may fix something dirty and broken, of the great friends I have made and the ways they have helped me, and I daydream in anticipation of the next time we cast off, liberated and venturing down a path unseen. To me, the dedication, skill, personal ownership, sense of adventure, steadfastness, and more exhibited by sailors is what truly makes it such a gentlemanly endeavor.
