I married into a sailing family.

I was raised in the Rust Belt, north of Pittsburgh, Pennsylvania, amid fields of corn, soy, and cows. I had gone a good 27 years without ever setting foot onto a sailboat.

Before my relationship with my wife, Chiara, whenever I thought about sailboats (which I will admit was hardly ever), I would conjure up images either of pirates hoisting the Jolly Roger as they prepared to plunder some poor merchant ship, or of people who had far too much time on their hands and who dressed in aggressive pastels and Top-Siders.

Needless to say, I often questioned the value of sailing and the motivations of those who owned sailboats. Hadn’t we moved beyond sails and scurvy?

Imagine my surprise when my inaugural visit to my in-laws’ home involved endless hours of our afternoons sailing on the Gulf of Mexico, off the coast of Florida. Southwestern Florida is known for its high-end shopping, manatees, pristine, white sand beaches, tourism, and saltwater fishing. Its backwaters and coastline are replete with powerboats carrying sun-kissed bodies and recreational anglers darting to and fro.

My father-in-law, Richard, owns a 2005 Corsair 24 trimaran, which he has affectionately named Just a Slice of Heaven. I can still remember looking longingly at those sleek powerboats as they sped past us, motors roaring, carving their way out into open water. We, on the other hand, had just spent what felt like an eternity with our sails limp and unfurled, waiting for the breath of a breeze to bless us.

They informed me we were “in irons,” and as the sweat dripped down my body, I wished someone would put me out of my misery, strap irons to my feet, and throw me overboard. My new family, however, seemed to enjoy this boring, humid hell, which further added to my misery.

“This is why they almost mutinied Columbus,” I thought, confirming my original convictions on the value of sailing.

Richard is a New England native and had spent his boyhood sailing with his older brother on the lakes and coast of Massachusetts. As a young man, he moved abroad and taught health and physical education for more than 30 years. He lived in many countries known for their stunning sailing environments (the Philippines, Indonesia, and Greece, to name a few) and was able to continue his love affair with sailing.

Forever the educator and sailor, he began to show me the ropes—bad pun intended.

One of the very first lessons imparted by Richard was that whoever invented sailing decided it was best to make up a smorgasbord of extra words to describe things already aptly named. For example, he would say, “The jib is luffing, trim the sheet!” For those of us who are more at home on terra firma, this would roughly translate to, “The front sail is not catching the wind quite right, pull the rope attached to it!”

My saint of a wife translated these inscrutable commands into something comprehensible to this landlubber, and so I trimmed the sheet. Apparently, there is a correct way to pull on a rope, and Richard was quick to alert me of this and model the more efficient and safer way to do the task that I had just accomplished (wrongly).

Many of the lessons Richard imparted on this tyro of a coxswain boiled down to how whatever rope he had asked me to pull could (and inevitably would) maim me or a member of my new family if it were not properly secured. To ensure the lesson was well-received, my teacher would couple his demonstrations with fun, vivid sailing stories about someone who had been mangled because of their lackadaisical rope handling.

So it went, me being tasked with pulling some rope, me doing it, and then Richard showing me how it should have been done, which was followed by a rousing tale of how “Ned” lost two fingers or how “Joe” dislocated both arms, and so on.

Every holiday they put me into this crucible of family fun.

I started out as merely a counterbalance. This was a simple job that consisted of me just standing on the windward amas whenever there was a strong wind (see what I did there, using that technical term, amas?). Eventually, however, I was given the honor of helming under strict supervision, which over time became light supervision.

As my hours logged on the family boat increased, my attitude towards this sailing business began to shift. It became apparent that the jargon I had derided was, in fact, necessary to differentiate between the plethora of ropes found on a sailboat. For example, the term “jib sheet” was much more efficient than saying the “horizontal red rope connected to the triangular sail.”

The more time I spent on the Gulf, the more I paid attention to small, subtle factors: the wind changing a few degrees, the clouds on the offing, the shifting tide, and so on. I was becoming responsive to these various details and could keep the boat moving forward (sort of).

Maybe sailing wasn’t all that pretentious or silly after all; it took specific knowledge, skill, experience, and work.

I will always savor the delicious memory of explaining to my wife the different points of sail and how we were currently beating, but we wanted to move to a broad reach so we could make it back to Delnor-Wiggins Pass State Park. She rolled her eyes and called me annoying. It would appear she was neither impressed with nor enjoyed my newfound nautical knowledge. Richard, on the other hand, gave me a big grin and a wink.

This past Christmas, he even gifted me with my first pair of Top-Siders; I may still be finding my sea legs, but I guess I earned my boat shoes!

As for those powerboats—they lost their luster a long time ago. Now I find their loud, interminable whining an ever-present annoyance, cutting through both wind and tranquility.

Possibly the greatest sailing lesson imparted by Richard is that the joy is in the journey and the reward is in catching the wind in your sails. Both are made that much sweeter when you can share them with the people you love.

It truly is just a slice of heaven.

Michael P. Hassett is a wildly inexperienced sailor, but what he lacks in know-how he makes up for in enthusiasm and poorly timed jokes. He is the co-founder and president of Friends of Tonga Inc.

April 2023