Routes to the Sailing Life
A look at how five families broke free and went cruising.
Certain decades in one’s life just seem to make it simpler to get to that point of untying the dock lines of your own cruising boat and sailing for distant shores. My wife, Windy, and I first did it in our 20s—before the house, the kids, and the careers. We had few ties to cut before sailing away for seven months to visit eight countries on a small, coastal, classic-plastic cruiser that I bought for $8,500. For many others, the cruising lifestyle is a goal only realized once they reach their golden years, when they no longer have to report to the office each morning and the kids are off on their own. These folks usually plan extensively for their escapes, and they possess the time and means to make it accessible.
But what about the folks who are, as author and blogger Mike Litzow has written, “serving the triple demands that people in their 30s and 40s find themselves beholden to: raising the kids, making a living, and, with whatever energies are left over, trying to organize things around some vision of what might add up to a satisfying life”? How do these families manage to cast off and anchor among the 20-somethings and the retirees? Given the apparent difficulties, what compels these sailors to make such a transition?
In just the past few months, which my family spent cruising along the Pacific coast of Mexico, my wife, myself, and our two daughters have crossed wakes with more than a dozen families who found such a path to the cruising lifestyle. Talking with several of them, I recognized familiar themes, though all of their stories were unique. I also heard what I knew: Yes, it’s hard work for a family to break free from a conventional life and transition to a vagabond existence aboard, but it’s definitely doable, even within modest means. Here are the stories of five such families, beginning with my own.