The sea, some say, is good to gamblers. The longer I ponder this proposition, the more depth I find. However, I’m allowed only one page, so I’ll stick to an area where it is highly relevant. Insurance. Sailing uninsured has always been an option for those struggling to afford a premium. The stakes are high but the odds on a sorry outcome are very long, especially for far-ranging ocean cruisers steering clear of crowded places with associated risks beyond their control.

I remember once enquiring about insurance for an old gaffer bound on a transatlantic cruise to rarely-visited venues. The response of the broker was salutary. She was a specialist in older craft and had been around the cans often enough to know a thing or two. The lady looked me up and down, examined the boat’s specification, then made her pronouncement in an old-school yacht-club accent, ‘You remind me of that dreadful man Tilman. It’s going to be expensive.’

I didn’t know whether to be downhearted or flattered. Major HW ‘Bill’ Tilman was my hero. He had sailed his pilot cutters in latitudes that could only be described as outrageous, danced with pack-ice and, sadly, had lost more than one historic boat in the process. The fact that he had enriched nautical literature with accounts that remain required reading for anyone who takes himself too seriously impressed neither the underwriters nor my broker.

A few years later, and despite the recorded misfortunes of Tilman, I declined an insurance quote for a trip to Greenland in a 1911 pilot cutter which he had once sought to buy. I owned the boat, but all my resources had been spent making her staunch, leaving me with a few fathoms short of nothing in the bank.

My shipmates were sharing the expenses of the trip and when the question arose of spending their money on victuals, which would benefit us all, or insurance, which would in all probability benefit nobody but the underwriters, the answer was a ‘no-brainer’. The reasoning was that if we ran into trouble in deep water or ended up nipped in ice, we’d fight like the devil to save ourselves. By default, this would involve keeping the ship afloat because nobody wants to punting around the arctic seas in a cheap liferaft. If wefailed, we’d probably go down with the ship, so whether or not I got my money back would be of no concern to anyone.

As for damage to the boat in coastal waters where salvation was probable, most uninsured sailors take at least as much care as those insured up to the gills. If damage were sustained, I carried a comprehensive tool kit for wooden boat repair, I was young and moderately capable. I’d handle it myself. As for the spectre of third party claims, there was always the advice of the foreman at the Elephant Boatyard in the Hamble. When confronted with a row of boats you’re about to hit, be sure to pick a cheap one.

Given the odds against disaster it all seemed fine, until I came unstuck in a big way. After successfully negotiating the fogs and ice of Cape Farewell and Newfoundland, my anchored boat was comprehensively rammed in New York Harbour by a large schooner under charter. With high-quality witnesses in profusion there was no serious dispute as to who had caused the collision. I raised a quote for repairs in a famous yard and was given assurances that the bill would be paid by the man who’d clobbered me. The job was a serious one and I was glad not to have to tackle it. That was until the bill was presented and the charterer changed his mind. A reputable insurer would have paid up then chased him for the money. As it was, the running was done by me. I lost a year of cruising, my hair turned white and all concerned ended up in the New York City courthouse. I walked out a free man with my bills paid, but I’ve never sailed uninsured since.

Tom Cunliffe October 2016 podcast

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