I have found that the romance of sailing is often enjoyed before and after the reality of passage making. So many people follow their dreams of boats and the sea and set out for the romance of days, weeks, or months under sail. They dream with Sir Francis Chichester, the first circumnavigator via the Clipper Route in 1966: “What bliss to be in the cockpit with the sun and the warm breeze on one’s skin, just watching the sea, and the sky, and the sails . . . ”

And so many people discover, sometime during their first offshore passage, that the best and most romantic of sailing stories are written when safely in port with the anchor securely set. As Hilaire Belloc put it: “The best noise in all the world is the rattle of the anchor chain when one comes into harbor at last and lets it go over the bows.”

In short, the reality of offshore sailing can be a harsh romance.

Cruising statistics tell us that roughly 40 per cent of passages are in contrary winds, 40 per cent in calms, 10 per cent in favorable winds and 10 per cent in storms. This seems true based upon what I have encountered. I met a fellow at the Liberty Landing Marina in New Jersey who built a steel cutter in Toronto and was on his way to Australia via the downwind clipper route (U.S. East Coast to coast of Africa, then to Brazil, then to Cape of Good Hope and then to Oz via the Roaring 40s). This traditional route turned for him into a passage of 70 per cent of the time beating into headwinds and contrary seas, and on two occasions of turning turtle (the boat rolled through 360 degrees). Not how he had planned!

This takes me back to the romance versus the reality. I enjoyed one of the most magical sailing nights of my life bringing a 46-foot ketch back from St. Thomas to Connecticut. The full moon was a beacon dead ahead, casting a glittering path on the water. I contentedly steered down that path, marveling at the great moon. After an hour or so, the sails began luffing and as I adjusted them, I wondered at the wind shift, as I hadn’t noticed a change. Then came recognition: “Duh, the moon moves from east to west,” as I dreamily steered down the glittering path, I was (duh) turning the boat’s course to the west. Fortunately, this was a time of moderate and favorable wind. Had it been rougher conditions, it might have been a problem. Ah, the romance of moonlight and the reality of wind shifts.

Since my children had grown up with sailing stories, in 2009 I took my 29-year-old daughter and 26-year-old son with me on our 50-foot cutter for a trip to Bermuda and back. My wife planned to fly to meet us, since as she put it, “Nothing goes through rough weather like a 727.” I gave my crew pens and little journals and asked that they keep a short diary of each day’s events to serve as a lasting record. We left with small craft warnings due to increase and stall over New England for a week. I decided to leave before the storm system established itself. Six hours south of Montauk, we were surfing our 50-foot boat down 16 to 22-foot quartering phosphorescent seas in 40-plus knots of wind with higher gusts. This kept up for 28 hours of downhill rolling, clocking off miles flying only a little jib.

The natural show was spectacular, the sailing was uncomfortable, the noises of rolling gear and slapping waves continual. Sailing settled down, as it does sooner or later, and we had a lovely couple of days to St. George. After our first dark and stormy (a Bermudian drink of ginger beer and rum) and after cleaning up the boat and washing the salt-soaked laundry, I asked to read the journals. (Remember the journals?) My son gave me that long-suffering son look. “Dad, who had time or energy to write anything?” My daughter gave me her journal; it had a single page of scrawl. “I am going to die. The waves are crashing around and the pots and pans are slamming in the galley. I can’t use the head without falling. Every time there’s a noise, I think the boat is going to break apart. I don’t think I’ll ever see my fiancée again. I’m scared and I hate this.” A succinct statement about the romance of sailing.

Several years ago on a beautiful Columbus Day, I took several friends out for a cruise in New York Harbor. Safely under way, I gave a friend at the helm instructions to head down the harbor keeping the Statue of Liberty to starboard, and went below to prepare lunch. After five minutes, I felt the unmistakable slowing and the gentle rising of a boat moving up onto a sandbar. I rushed up the companionway but couldn’t get us afloat in a falling tide. Aground on Columbus Day at the Statue of Liberty, surrounded by tour boats, Coast Guard boats, New York Harbor patrol boats and New York fire department vessels. My crestfallen helmsman/guest protested: “But I did keep the Statue to starboard!” It was my mistake. The Statue of Liberty is on an island and the literal interpretation of my instructions had the helmsman carefully circling the island rather than heading down the channel.

I pumped all the fresh water out of the boat to lighten her, then tied the masthead to an anchor to heel her. Finally, I ran out of tricks and waited for the tide to reach low and then rise again. We floated off at the high tide.

But before that, I had decided to use the time aground to finally clear the forward head’s through hull fitting. I got in the dinghy and stuck a clothes hanger into the fitting; now aground, it was high and dry. I freed the blockage and was showered with gallons of toilet waste. Remember how I had emptied the fresh water to lighten the boat? I’m sure I am one of the few people who has cleaned himself in New York Harbor water.

It was only back in port (and several years later) that the sailing story became romantic. Or perhaps I finally became able to regale people with the reality of my dumb sailing adventure.

Jim Malkin lives in Chilmark.