By rough count, more than 60 different people have sailed with me on my boats.

No, I haven’t been operating a day charter business on the side. What I have been doing is sailing in sailboat races for a long time. Those 60-plus men and women, and a few teenage boys and girls as well, came to sail in races as members of my crew.

Sailors who prefer cruising, daysailing and just spending time on their boats at the dock have told me they eschew racing because they don’t want the pressure of competition to intrude in the simple joys of sailing.

I get that, and in hiatuses from racing I like to enjoy my boat in exactly the laid-back way they do. But for those of us who sail in races, the competition only adds to that enjoyment.

Most of us are programmed to be happy when we win, and sailboat racing, at least at the sub-grand prix levels where most of us compete, makes winning fairly easy. Yacht racing has embraced the “podium finish” ethic of the Olympics and awards prizes to competitors who “win” them with second and third place finishes, and in some races even with fourth or fifth place finishes. Trophies inevitably accrue. Dust covered boxes of these tchotchkes can be found in the basements and garages of habitual racers.

Other sailboat racing awards are found far beyond the podium. Racing rewards us by getting us on the water. Racers typically sail hundreds of miles each year, far more, I’d reckon, than all but the most dedicated long-distance cruising sailors. Those miles are sailed in the full array of sea, wind and weather conditions, testing sailors’ skills and providing experiences that stoke enduring memories.

And then there are those kindred sailing spirits you meet along the way. A number of the scores of people I’ve sailed with have become lifelong friends. 

A young man who was a precocious member of my crew as a high school student went on to college, joined the sailing club there and got the bright idea of inviting club members to come to his hometown on weekends to crew on boats sailing in the local racing series. 

The university students were mostly fast learners, young and fit and fun to be around, but one of them was a standout. While we were sailing back to the harbor after a race, with the boat heeling at a sharp angle in a strong breeze, he walked up the windward side of the mast, waved from the masthead and made his way backwards to the deck.

I think he just did it for the fun of it, but if it was meant to get the skipper’s attention, it worked. I soon learned he not only was undeterred by any physical challenges encountered on sailboats, but was a natural born sailor. He has since sailed with me for decades as a mainstay of the crew and a spot-on reliable navigator.

One day, a 20-something-year-old man came to my office and told me he wanted to apply for a position. I thought the well-dressed and articulate fellow wanted a job on the magazine. It turned out that what he was applying for was a position on my sailboat racing crew. He told me earnestly that though he was new to sailing he would learn quickly and be an enthusiastic contributor to the success of the boat in any role we designated for him.

That was 33 years ago. He was true to his word and became a skilled sailor who to this day energizes the crew with his unflagging spirit. Meanwhile he wrote a seminal book about reviving family sailing and after a successful business career started a new career as executive director of a large community sailing center. 

Some of my most memorable crewmates displayed interesting but harmless foibles in our racing adventures. Like the two sailors who came as a package, buddies with stellar sailing resumes.

They were terrific additions to the crew, true renaissance men of sailing who could calmly and expertly perform any task on a racing sailboat, from steering in a downwind blow with a spinnaker on the edge of a broach to strategizing the next move up the course. 

Alas, the latter frequently tested the buddy relationship. Tactical decisions, even basic ones like whether to jibe to cover another boat or stay on the favored jibe, ignited epic arguments between the two, fought with the intensity of a courtroom drama (one of the buddies was a lawyer). Often the arguments went on unabated after the skipper had made the decision they were fighting over. The rest of the crew regarded the debates as diverting entertainment.

One of my mates was built like a Michelin Man with muscles (and muscular genes—his daughter became a champion weight lifter). His specialty, naturally, was winch grinding, and he was good at it. Several years after he left the crew, I was informed that his frequent trips to the head in long distance races were not for the usual form of relief. On a boat where, by skipper’s edict, alcohol is never consumed during a race, he had secreted a stash of a fermented malt beverages and chugged cans of it in his visits to the head. It didn’t seem to affect his performance.

Speaking of alcohol, my crews over the years have included three alcoholics (that I know of). They were capable sailors and, unlike the thirsty grinder, never indulged their addiction on the boat (again, as far as I know). The most colorful of them brought with him not a bottle of booze but a bulging seabag of hair-raising sailing experiences, which served the crew well with entertaining stories and, when the going got tough, the confident effort of a sailor who had seen it all. 

He and the others mentioned here are just a few of the 60. The dust continues to settle on the boxes of tarnishing racing trophies, but the sailboat racing friendships are as shiny as ever.