After a few elementary instructions, the new mate learns by experience. For instance, never tie up the peapod painter with a slippery hitch. Having her go adrift once is sufficient experience.

We were beating out of the harbor with a full load of six passengers in our Friendship sloop. The mate was on the foredeck coiling down the jib halyard. From the wheel, I called, “Jon, clear the weather sheet.” Jon looked puzzled. What was the weather sheet and to what? “Jon, the weather sheet!” The jib was backing and forcing the bow away from the wind so I could not tack as we approached the shore. Jon quickly saw that the windward jib sheet was fouled around the bit and cleared it in time. “Windward” he knew, “weather” was not yet in his vocabulary. Let the topsail sheet go aloft and it will soon be in your vocabulary.

On another day, we were planning to set a different mate ashore on a float to which was tied a Coast Guard launch. In the lauch were two men, one holding erect a galvanized pump and the other pumping dirty bilgewater over the side. My idea was to luff by the Coast Guard boat, and as we glided gently by, the mate would step daintily over. But I didn’t glide close enough. I called, “Don’t Jump!” but it was too late. She was already airborne. She shouted, “I’m boarding you,” and landed in a clutter of arms and legs, pump and bilgewater. I, of course, glided on. Sailboats have no brakes. Both of us learned from that experience.

On another pleasant day, Jon and I took out the Governor of Illinois with his wife and three children. His son, aged about 12, was wearing proudly his new sailing cap with a shiny visor, a white top, and fake gold braid. We had had a good sail and the Governor had taken pictures of his son at the wheel with his new cap tipped jauntily over one eye. We were homeward bound before the wind with Jon at the wheel.

“Be careful, Jon, and don’t gybe,” I cautioned. We sailed on for a while very happily ’til Jon edged too far to leeward, the wind got on the forward side of the sail and we gybed with a crash and rattle of blocks. Nothing broke, but the son’s hat went over board and was left bobbing astern.

Both Governor and son leaped up to swim for it. I said, “We’ll go back and pick it up. Keep watching it and pointing to it.” Jon and I had practiced Man Overboard several times. I trimmed in the main sheet. Jon doused the jib and trimmed the staysail. We tacked to get the hat on our weather bow. Jon picked up the boathook and stood by the rigging. I luffed, and as we slowly approached the hat, now partly submerged but visible, Jon harpooned it with his boathook and handed it dripping to its owner.

The delegation from Illinois learned about Man Overboard. Jon learned that if the wind blows on the back of your neck on the same side as the mainsail, you better duck, and we both had another good practice at Man Overboard.

A regular contributor to Working Waterfront, Roger F. Duncan is the author of Maine: A Maritime History, and other books.