We live in a 9-to-5 world, our calendars, computers and appointment books jammed with scribbled must-dos and don’t-forgets, and we have very little time that isn’t scheduled. The very concept of “spare time” has disappeared from our vocabularies. Kids scurry from soccer practice to dance lessons without pause for either kid or parent.

On a charter, though, you can leave all that nonsense at home.  

In the olden days of wooden ships and canvas sails, the captains never, ever, wrote the words “going to” in their logbooks. They always listed their voyages as “bound for” and therein lies a world of difference.

“Bound for” leaves enough slack so that they could end up anywhere in the world without feeling badly about it. If the winds were against them, or they had a problem en route, they just went somewhere else. No big deal.  

When it comes to bareboat charters, I admit it: I used to be like many of you. I couldn’t resist planning my charters from start to finish. It was, for those of you old enough to remember the movie, the “If it’s Tuesday, this must be Belgium” mentality. We weren’t getting on a tour bus every morning, but I knew where we would anchor each night, sights we would see, reefs we would snorkel, and pubs we would suck dry.  

But then I sailed as a guest with some friends who were almost fanatically committed to the unplanned adventure. The theme to their entire lifestyle might be called “Plan B.” As we cast off the lines on the first day of our charter, we had no idea where we were heading. We had two or three good options, of course, but we let the wind be our guide.  

Literally.

As we cleared the harbor, we looked to see which way the wind was blowing, and went with it. Only then did we check the chart to see where we were headed that day. It put fresh meaning to the words I remembered from the 1960s Vince Guaraldi song, “Cast Your Fate to the Wind.”  

“I set my sail as the tide comes in, and I just cast my fate to the wind.”  

It was, from start to finish, an absolutely delightful charter without my train schedule mentality.  

We lingered over breakfasts, enjoying the morning coolness without having to rush to our next destination. We would up the anchor at midday, sail for a while, and then look at the chart to see where we might anchor for the night. In fact, on our third day, or maybe it was the fourth, possibly even the fifth, we didn’t go anywhere.  

At all.  

We liked where we were anchored and we were content to savor the whole day: snorkeling, beachcombing, reading in the cockpit, sipping a rummy cocktail. We met some cruising folks on the beach and joined them on their boat at happy hour to watch the lemminglike rush of arriving charterers who were on The Schedule.  And we smiled with delight at our own relaxed attitude.

“I shift my course along the breeze, won’t sail upwind on memories.”

Since that time, I’ve become a convert, mostly. I’ve managed to throw away the minute-by-minute schedule. Now, on a seven-day charter, I have a mental list of three or four places I’d like to visit. If we make it, great.  But if not, no problem. Refer to Plan B.  

Rick Steves, the ubiquitous travel writer, has a basic piece of advice for all his readers, whether seasoned or novice: “Whenever and wherever your travel, let your default response be this: YES.”  It’s solid advice for charterers as well.

If you’re sailing near an island and spot a beautiful beach with not a person on it, the answer to “Should we stop?” is YES. What do you think about having dinner at that little restaurant near the marina?  YES. What if we skip the expected second-night anchorage in favor of one the charter company mentioned?  YES.  

In the process, She Who Must Be Obeyed made friends with a couple running a tiny beach food stand who were more than happy to make grilled ham and cheese sandwiches for us. We still get Christmas cards from them. I know an amazing snorkeling reef that even locals don’t know, simply because we said, “Sure, why not?”  YES.

As a result, I’ve mellowed, knowing that I’m likely to find a handful of wonderful places I never knew existed. So it all seems to balance out rather nicely. The discoveries are serendipitous, and often a lot more fun than a scheduled destination.

The sheer vagaries of wind and weather on a charter are a refreshing and much-needed change from our over-regimented world.

“I wonder how it might have been, had I not cast my fate to the wind.”

Trust me on this: You won’t regret it!