Florida Man Buys a Sailboat in Massachusetts in October By Paul Trammell
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lorida Man has certainly done some foolish things, but buying a sailboat is not one of them. In October of 2019, after selling my house and purging myself of the vast majority of my material possessions, I packed all my remaining belongings into a U-Haul trailer and pointed my old truck north. Windflower, a 1972 Cartwright 40 that I had under contract, was waiting for me in Mattapoisett, Massachusetts. She had been on the market for over a year and I essentially saved her from being sacrificed to destruction for salvage. Even though nobody else seemed to want her, she was just the right boat for me: a stout bluewater cruiser with a flush deck, a cutter rig, and a full keel. I was nervous about buying a boat so far north in the fall. She was not expensive, rather far from it, and I knew I would have to work on her for a month or two before she was ready for ocean sailing, and I needed to go ocean sailing in order to escape the northern winter. I was nervous both about working on her for two months in the cold, and about sailing in the North Atlantic in the winter. I’m built more for the tropics than the arctic. I considered having her moved over land to Florida on the back of a truck. This would have cost around $7,000, but would have been very convenient, as I would have been able to take my time working on her in the warm climate with which I am familiar and comfortable. However, I wondered if the money could be better spent. In the end, I talked an old friend into coming with me and I hired one other person to help me move her to the Chesapeake Bay, which cost me about $900. But before I could sail her anywhere, I worked on her for about a month in Mattapoisett at the Mattapoisett Boatyard. Mattapoisett is an exceptionally beautiful place. Every scene around town could be on a postcard. The houses are charming and were clearly built with an eye for aesthetics. The trees are tall and hang over the roads, bursting with fall colors of red, orange, yellow and all the combinations between. A quaint lighthouse sits at the end of the street past the marina, looking out over Buzzard’s Bay and welcoming the nocturnal sailors. The landscape is threedimensional, not the flat land that I am used to. I felt welcomed here and quickly developed a sense of home. I also noticed right away that the people up there are all friendly and helpful. As soon as I pulled in to the Mattapoisett Boatyard, I needed a hand. I wanted to park the trailer and get it off my truck, but U-Haul trailers apparently don’t have jacks to lift them off the hitch. The yard workers offered to use their forklift to lift it off, but the three of us managed by risking our backs instead. This was the first of many instances of friendliness and helpfulness that I experienced up there. October in Massachusetts is much like January in St. Augustine, Florida. Don’t let the fact that the locals are wearing shorts fool you. It’s cold by our standards. The
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temperature regularly plummets to near freezing in October, and the sun sets earlier and rises later that we remember it doing down south. Proper clothing is a must, but first, as Southerners, we have to face the fact that we know as much about proper winter clothing as Yankees do about alligators and banana spiders. Florida Man needs serious winter clothing just for fall in Massachusetts. Long pants and closed-toed shoes are not enough. Boots and long socks, preferably wool or something similar are essential for keeping the feet warm. Leave the cotton where you found it. Cotton holds water and thus perspiration. It is not a good insulator after it gets wet, and it stays wet inside a boot. Little ankle-high Florida socks are no good here. You need tall socks made for winter. Sock liners are also a huge help. They wick moisture away from feet and this keeps the feet warmer; warm feet are a blessing while cold feet make Florida Man want to stay wrapped up in a sleeping bag dreaming of hot sand on the beach in summer. Sock liners, warm moisture-wicking socks, and warm boots are a winning combination. Long pants are a must, but again, leave the denim and cotton at home if you are going sailing. Get some waterproof pants. Yes, they exist, and if you look, you will find them. When it’s really cold, a good combination is long underwear, synthetic workout pants, and offshore bibs. Pro-tip: take your bibs to a seamstress and get them to install a fly so you can pee without having to take off your lifejacket, then your coat, then your suspenders. By the time you’ve taken all that off you’ve likely peed your pants. I’m not sure how women handle this situation, but
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