I must confess, I’m a bit of a geek when it comes to plotting a float plan. Maybe it’s the anticipation of casting off lines and setting out on another adventure. Or maybe it’s just my inner control freak taking over. But for me, there’s nothing more pleasurable on the eve of a cruising leg than rolling out a paper chart with a set of parallel rules and a pencil, and etching out some lay lines.

But, as with life, cruising doesn’t always work to schedule.

I recall the last day of a perfect long-weekend cruise with my in-laws on their Meridian 490 Pilothouse Island Time. They had twisted our arms just enough to persuade my wife and me to join them on a diversion from their Great Loop expedition, spending a few days exploring Block Island and Martha’s Vineyard in New England.

Sunday’s return plan was simple enough: Wake up, enjoy a leisurely bacon-and-eggs breakfast aboard Island Time, and then roll out of Vineyard Haven at Martha’s Vineyard mid-morning to arrive at Newport, Rhode Island, around lunchtime. My wife and I could then catch an afternoon flight out of Providence. We both had to be back at work in Fort Lauderdale on Monday morning.

As our Island Time crew began to stir around daybreak, a chorus of metal shrouds and stays slapping the masts on some neighboring sailboats was of some concern. We had checked the weather the night before and were expecting a lumpy ride, but to what extent was speculative. Not wanting to take any chances of missing our flight, we forwent the leisurely breakfast to allow ourselves more time to get there.

Departing Vineyard Haven into a sea of whitecaps, we made the gradual turn from northwest to southwest, hoping to catch some lee in Vineyard Sound. The northeasterly breeze, however, allowed little protection, and the more the sound opened up, the more we pounded.

Our saving grace was a cut through Robinson’s Hole, a passage that Vineyard boaters regularly take through the Elizabeth Islands. Seven buoys mark a narrow channel. Once in it, we felt like the whitecaps visible at either end provided an eerie solace—it was as if we were in the eye of a hurricane, which would have seemed even cooler were we not busy sizing up what awaited us at the other end. The calm did provide a brief respite to down breakfast and a cup of coffee.

Round two was a mad dash to the finish line, pounding straight into short-interval 5- to 7-footers all the way down Buzzards Bay and into Rhode Island Sound. My father-in-law and I manned the flybridge helm together, soaked to the bone, taking green water in the face like we were being waterboarded. It was a hell of a ride, and far from the “happily ever after” we had mapped out the night before.

Even the best-laid lines on that crisp paper chart couldn’t account for the elements beyond our control, which is why you should never boat on a schedule. Much more than the obvious logistical nightmare a schedule can pose, it can suck all of the fun out of the cruising experience.

On that beater to Newport, the most important thing about boating—enjoying it—was the last thing on my mind. Instead, it was the worry of variables that were out of our control: Were the wives OK down below? Were we going to miss our flight? Was I going to damage my in-laws’ boat trying to keep to a schedule?

Save those qualms for the next guy. Next time, I’ll change my flight.