Cruising: Revisiting the Dream of Vagabonding

Sail News

Back at sea: the author and his wife decided it was time to cast off lines once more

While neither my wife, Ivy, nor I came with a sailing pedigree, there has always been a sailboat in our marriage. Now, with our careers approaching their final curtain, we’re drafting plans to cross old waypoints and establish new ones as we retrace a journey that takes us back to our beginning.

We’re no longer the neophytes we were when, as newlyweds, we set a course that took us outside the lines of convention. Leasing out our home in Hawaii and loading all our hopes and dreams into our low-tech 36ft cutter, we sailed through the first 10 years of our marriage while bumping along the Left Coast of Canada, the United States and Mexico. Schooled by a decade of shivering and sweating together in close quarters, the three of us—Ivy, our marriage and I—were soon tempered and bonded in the crucible of a small sailboat at sea.

Bigger boats also bring bigger demands

Bigger boats also bring bigger demands

Discovering that vagabonding enriched our lives in a currency too few seemed to value, we postponed our return to Hawaii. Throwing in for a penny or a pound, we sold our beginner boat and acquired a sleek, modern 47-footer we found in Florida. After that, our second decade of marriage found us harbor-hopping along the Right Coast of North America, eventually transiting the isthmus and making a rhumbline back to Hawaii to complete the final grind of our careers.

Since returning to Hawaii and adhering to a 10-year “scrimp and save” plan, we and our sailboat have not sat idle. Bleeding a river of sweat and elbow grease into our seaborne citadel, we’ve renewed our vessel and are convinced she is ready to escort us to new destinations we’ve long dreamed of.

Regrettably, the same decade we spent hardening our sailboat has also softened our bodies and rounded some of our edges. As we plot to sever the safety net that our careers have provided, Ivy and I recognize that cruising at our age presents challenges that did not exist 30 years ago.

Our sabbatical from cruising has also, in addition to enabling us to acquire an inventory of possessions, created in us a sense of ownership. Trading my wife’s awesome car and my beloved motorcycle for long, hot walks in flip-flops under a tropical sun through dengue and malaria-ridden backwaters, no longer holds quite the same charm it did when we were in our thirties. Surrendering our cushy existence to return to a life of uncertainty and discomfort, a life that will include “sporty” weather, night watches and the occasional worrisome anchorage makes us take a deep breath.

Easily, the leading cause of our increased cost and consternation is the fact we’re no longer young and no longer on a 36-footer. Cruising in our earlier years, we laughed at the idea of “wasting” money on any kind of insurance other than some extra chain and a bigger anchor. While we remain blessed with good health, the prospect of sailing into the winter of our lives without feeding the beast that is medical and property insurance seems like courting disaster.

A return to vagabonding will also require that Ivy and I step back from the pinnacle of our careers with the resulting loss in earning power. I expect to wobble a bit while trying to recall a tempo that I haven’t listened to for a long time. Patently aware that a failure at our age may prove harder to recover from, we still hold to the tenant that life is uncertain, hedged by educated planning and cautious readjustment. Whether it’s choosing a career, opting to not have children or cutting dock lines, we’ve never expected, nor asked for any guarantees.


While there’s only so much to be done for our clogging arteries, one thing we can do is relearn how to enjoy life by remembering that aging well is an acquired skill. Ensconcing ourselves in a retirement comfort zone might runs the risk of sowing the seeds of stagnation and “senioritis.” Electing to navigate both the good and bad that is inherent in the cruising lifestyle, we hope to reawaken old muscles and return to a less scripted version of ourselves and our changing planet.

And so, last May, Ivy and I quit our jobs and unfurled our dreams as we reached from Hawaii and rode the trades to Kodiak. Why Kodiak? Because cruising Alaska forces us to redefine our comfort zone. The world and weather are evolving. The higher latitudes have never been warmer. We’ve come to see blue ice because, like me, the glaciers are old, cracking and may someday cease to exist. Eventually, we’ll meander down the West Coast as we did so many years ago, attempting to smell any roses we may have missed the first time around. Periodically, we’ll take inventory and reevaluate if we’re still having fun.

Why am I telling you this? Because you might be me. Because you might be old enough to recall that your first set of keys belonged to roller skates and with most of the sand in the bottom of the hourglass it becomes pointless to beguile yourself. You’ll never be younger than you are today. The fruit of your labor is best picked at peak season. Eventually, time becomes more precious than money. Maybe it always was. Hope to see you along the way. Aloha! 

Photos by John Cruz

January 2021

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