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Robert’s Substack · Aug 21, 2026

Family Sailing Chaos

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Robert Issenman · Robert’s Substack

My older brother first learned to sail small boats at camp in #Algonquin Park. In sailing as in most other areas, Phil never questioned his own prowess. He lives by the principle of “Ready, Fire, Aim”. Looking back, we have shared a series of sailing experiences that became more of an adventure than may have been absolutely necessary

The first occurred on Cape Cod’s #Hyannis River. My mother was inescapably drawn to this place so closely associated with the Kennedy family. So, it was no surprise that on a family vacation to the Cape, we set out to rent a small skiff for an afternoon river sail. Phil would have been 14 and knew a great deal about sailing on Algonquin Park’s Canoe Lake. He had not yet learned that other boats were rigged quite differently than the hardy Albacore camp boats he knew so well.
We all piled into the small boat, picked up a stiff breeze and slid smartly away from the dock. No sooner had we caste off, than pandemonium ensued. The marina staff were waving arms and yelling. We waved and shouted our greetings back to them. They waved even harder. We slowly came to understand the source of their enthusiasm. We had somehow snagged a rope connecting the rest of the marina’s fleet of small boats but were not at all slowed by the eight skiffs that we towed behind us. As in the movies, one of the crew leapt into the water knife between his teeth and cut our boat free. Thus liberated, we careened away from the dock and ploughed towards hundreds of yachts with smooth polished mahogany hulls bobbing at anchor in the middle of the river.

The boat’s rudder was not responding to the tiller which Phil jammed from starboard to port in a fruitless attempt to control the speeding vessel. My father rapidly assessed the hundreds of thousands of dollars damage our small craft would do to these priceless yachts. Without regard to his own safety, he threw himself into the breach fending off the yachts with strength and determination we didn’t know he possessed. Still baffled, Phil determined that the boat’s problem was the excess weight of the crew. By this time, we were three quarters of the way across the broad river. I still don’t know what instinct motivated my mother! We sat transfixed as she rose from her place and dove over the side of the boat and started to swim several hundred yards to shore.
Further lightened, the boat was picked up by the wind and hurled downstream. My sisters sat in shocked silence as my mother’s shape grew smaller and smaller until she seemed like a spider slowly plying her way to shore. Finally, Phil realized that our centerboard needed to be lowered, and the boat responded as desired. We spent the afternoon tacking laboriously up the river, returned the boat and found my mother who had successfully made it to shore, walked to a bridge two miles upstream and back to the marina in a salt-soaked sundress looking not at all like Jackie Kennedy.


A number of years later, Phil and I were both much older, married with children. Phil decided to lease a beautiful 48 foot Hunter. It was moored in Port Douglas at a yacht club on Lake Champlain’s northeastern shore. My son Michael, and daughter Kate, joined Phil and his friend Patricia as a stiff fall westerly breeze blew across the narrow harbor.

We headed out to the Lake. Out beyond landfall, we caught gale force winds which filled the sails and hurled the boat across the head of the lake towards Burlington, Vermont. It was an exhilarating sail until we attempted a come about and the boat heeled over on its side. I looked up just in time to see the outboard motor which had been lashed to the top of the transom, break loose and slowly tip over the side into the water. With a distinct gulping sound, #Lake Champlain swallowed the motor as our yacht sped rapidly away.
Phil shortened up the sails, and we beat our way back to port. However, once home, we found the winds swirling around the harbour. Despite lowered sails and motor power the boat responded sluggishly. We putted up the narrow dock channel but each time we turned into the slip a gust of wind would catch the boat broadside and move us perilously close to one yacht or another. I blurted out a suggestion to the captain, whereupon Phil threw up his hands, walked away from the helm saying something to the effect of “If you think you can do better.......”

I took the wheel. Oversteering, I managed to spin the 48 feet of boat in the 60 foot channel several times. Yacht owners poured out of the club house grabbing gaff poles and ropes to defend their property in the face of this spectacle. Finally, Phil recovered enough to take the helm and with the help of onlookers successfully brought the boat into its slip. We went off to find how much we owed for the lost motor as the women and children ran from the humiliating scene to the refuge of our cars.

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