This lesson I learned on a Pacific Northwest cruise applies to day-in, day-out boating experiences for us all. But, first, let me introduce the Three Princes of Serendip.

In case you slept through the classes on Persian fairy tales and 17th-century English (Horace Walpole stole from their poem), the Three Princes of Serendip were from a mythical land whose king was their father. He sent them in search of a lame camel. Their path to discovery is marked by accidents and whimsical misjudgments, leading them to wondrous adventures.

Now, this may seem far afield from boating, but here’s the bottom line: Too many of us have everything planned on our outings, whether we are out for an afternoon cruise or a monthlong voyage. And that takes some of the joy out of boating, which should be about surprises and adventures and, yes, more than a touch of serendipity. A travel writer I have long admired often gives this piece of advice: “Whenever and wherever you travel, let your default response be this: Yes!”

For bareboaters, this means deciding to spend an extra day in a cove with a sandy beach and a reef for snorkeling. It means skipping the overnight stop you’d planned so you can instead take advantage of the little beachfront restaurant your checkout instructor said had “da best burgers, mon, and Painkillers, too.” Don’t resist. As the Vince Guaraldi Trio sang, “I set my sail as the tide comes in, and I just cast my fate to the wind.”

But this advice is not just for skippers on a charter. Let it take hold in your everyday boating. Try out that distant harbor you’ve never explored. Or, close your eyes and point at a local chart, and then go to the nearest port to your fingertip. Your boat isn’t limited to paved roads like your car is on land. Make up your own course and set it.

In the days of square-riggers and iron men, the captain never, ever, wrote the words “going to” in a logbook. The crew always set sail “bound for,” which gave them the slack to go anywhere the wind pushed them.

For a long time, my mentality was: “If it’s Tuesday, this must be Belgium.”
I was all about the rigid tour-bus scheduling found in the 1960s movie by that name. But then, I hung out with an old-timer aboard his rugged North Sea trawler in the San Juan Islands off Seattle. He was of an age that he operated entirely on Plan B. He would look, every morning, at the weather forecasts. But he might as well have thrown a dart at the chart; we went wherever, stopped whenever, lingered if it continued to please us (food, wine, friends on nearby boats), and were prepared to yank anchor at the exact instant that any of those things no longer held our thrall.

We were, in the spirit of the travel writer, always willing to say yes. Even late in the day, we might move just a couple of miles to plunder virgin territories. Our inspiration might have been a reliance on Serendip, or a dockside mention of a marina whose restaurant had fab vichyssoise, or a notion of finding better sunset views. The answer was always, “Sure, why not?”

I now live with a Plan B outlook that extends to my life ashore. If we spy a hole-in-the-wall diner at a truck stop, we’re often tempted to see how it does with patty melt sandwiches. Or meringue pies. Forget the well-worn restaurant that was our original destination.

Boating is a wonderful opportunity for serendipitous discoveries, which are often a lot more fun than the planned destination.

Trust me on this: You won’t regret following in the footsteps of the Three Princes of Serendip. 

This article was originally published in the July/August 2023 issue.