Florida Man Buys a Sailboat in Massachusetts in October

By Paul Trammell

Florida 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 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

it is something to think about.

Layers, layers, layers. Yes, multiple layers of clothes will keep you warm. Don’t ask why, just do it, and don’t use cotton, at least not as the first or last layer. Start with a thin synthetic long-sleeve shirt and tuck it into your pants. Next up is a thicker shirt, move on to a fleece or wool sweater, and top it off with a waterproof and windproof jacket. The expensive Gore-Tex jackets are great if you can afford them. The generic versions are nice too. But your first purchase should be inexpensive foul weather gear made for commercial fishermen, like Grundens or Stearns. These simple PVC Jackets and bibs will keep you dry after the expensive gear is waterlogged. You need more than one set of foul weather gear anyway, because it’s going to get wet.

You can’t go wrong by bringing too much cold weather gear, so pack up hats, scarves, neck warmers, and gloves. You’ll need lots of gloves if sailing offshore in the cold. They get wet and need frequent replacing. I buy cheap gloves from Home Depot made for construction workers, and I buy lots of them. This way I always have dry gloves. I also have inexpensive ski gloves for when it’s really cold, and some gloves leftover from my mountain-biking days. Even when it is warm, it’s a good idea to wear full-finger gloves when anchoring. The heavy anchor and rode can take a finger right off, and cheap gloves can prevent this.

A friend who works on commercial fishing boats recommended the Mustang Deluxe Anti-Exposure Coverall and Worksuit. This is a warm and waterproof one-piece suit with built-in floatation, a hood, and big pockets. It’s less expensive than a high-end foul weather jacket. I bought one, and will let you know how it works soon, but I have high hopes. You can find them at Defender for a good price.

Choosing a weather window to sail from Massachusetts to the Chesapeake Bay in late October is a daunting task. Low pressure systems, often nor’easters, roll off the coast with a disturbing regularity and whip the North Atlantic into a cold frenzy.

While I was in Mattapoisett, a nor’easter developed 50 knot winds, sustained, and it lasted for two days like that. The passing of this storm left me anxious about choosing the right time to leave. Thank goodness for modern weather forecasting.

Windflower and I left Mattapoisett with two crew at 4:00 a.m. October 23rd to catch the outgoing tide. Although the temperature was a pleasant 61 degrees, the fog was thick and Albert, my paid crew, stood at the bow with a spotlight looking for mooring buoys, of which there were many in the bay. The fog was so thick that as I looked ahead at Albert and his spotlight, I started curving off to starboard. I was a bit shocked when I looked at the chartplotter and we were heading towards land and shallow water. It took my fogconfused brain a minute to grasp the situation. Becoming disoriented in fog is real, and I had to put my trust in the chartplotter, which took a moment of conscious thought.

Soon we were out in Buzzard’s Bay and sailing, which would have been fine had it not started raining. I didn’t have a bimini yet and had to just sit at the helm and take it. Oddly enough, nobody mentioned that it was raining, and I suppose it was obvious enough and complaining certainly would have done us no good.

After clearing out of the bay and entering the Atlantic Ocean proper, I was able to kill the engine and point to sea. The wind came up to 20 knots, and we made 7. I was

Cruising & Sailing Florida, The Southeast & The Bahamas thrilled; my new old boat could sail! Windflower charged through the 4-6’ seas all day and I wore a broad smile while I sat at the helm of my new vessel and home, sailing her offshore for the first time. However, Albert got very seasick and became incapacitated. My other crew was an MD, and she and Albert convinced me to sail towards Long Island to get in the lee of the land and thus calmer water so Albert might recover. He was vomiting every hour or so and she was worried that he might get dangerously dehydrated. I reluctantly agreed and we tacked toward land.

Night set in and I stayed at the helm a long time. Needless to say, I was very cold. One crew was nearly hypothermic and effectively immobile, the other was still sick. I did what the situation asked of me and sat at the wheel dressed as warmly as I thought necessary before leaving the interior of Windflower. It’s hard to gauge how much clothing to put on when inside a boat. Outside it’s always colder and the wind exacerbates the discomfort. On my next cold-weather journey, I intend to keep a plastic Ziplock bag full of gloves and hats and HotHands in a lazarette in the cockpit. This way I will have a much better chance of staying warm while at the helm. As soon as my gloves get wet, I will replace them. If I need a hat or the extremely warm neck warmer, or a facemask, I will have it right next to me. Windflower sailed into the Chesapeake Bay on October 26 in warm and sunny conditions and we took a slip at the York River Yacht Haven.

I’ve been here for about five weeks now working on the boat. The main chores have been installing new hatches, a powerful below-deck autopilot, a solar panel arch, solar panels, new batteries, and raising the roller furler higher off the deck so I can hoist anchors beneath it (the furler was mounted about 2 inches above the anchor roller).

November in Virginia is similar to October in Massachusetts, or perhaps a bit colder. Soon Windflower and I will set sail for warmer climes, perhaps The Bahamas, or perhaps Martinique, or I could shoot for the middle and go to the Virgin Islands, and there’s also Bermuda to consider. I might just make my decision while I’m underway, for what better way to choose a destination than to let the wind decide for you?

Paul Trammell is a solo sailor and author of four books, which can be found at Amozon.com. His latest sailing nonfiction is “Journey to the Ragged Islands.”

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