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  • Tristan Sess

Day One

Updated: May 12, 2021

Everyone’s dream after graduating from college is to move back in with their parents with no clear vision of what’s next… right? Well, it wasn’t exactly what I planned, but it is what ended up happening and it wasn’t all that bad. My brother and his girlfriend moved in too and we all had a blast that summer. More importantly, I fell in love with sailing again. After just one trip out on my dad’s power boat that Spring, and a few extra dollars in my pocket, I really struggled to find a reason NOT to buy a boat of my own. After all these years, it was finally time. I hadn’t sailed since early college, nearly five years ago, and I had really started to miss it. When I stopped sailing, it was because I was burned out. Competing at the top of the national circuit was stressful, and throw the pressures of a military academy on top of that and it was becoming hard to enjoy. But now, with a long summer ahead, and competitive sailing behind me, my the only stress I had was figuring out how to get out on the water as much as possible and how I was going to convince my dad to let me use his boat for the day.

I mentioned I had a few extra dollars in my pocket, but when I say that, we’re talking about $1000, not 20k, just for some perspective. The moderately maintained and decently outfitted boats were completely off my radar. When looking at prices I was really only looking at boats that were… well, free. That quickly changed after realizing that taking a boat off someone’s hands was going to cost me more than a boat someone wanted to sell. After a few weeks of searching, I eventually came across a Seafarer Challenger, a 23’er, and in pretty good condition as well. The best part about it was the price. Only $800! I was pretty sure there had to be something wrong with it so I called the owner up to talk. It turned out he was moving to Colorado and had to sell the boat before he had to start paying summer slip fees. My lucky day.

I messaged the seller, ready to buy it immediately, however, he told me I was too late and that he was selling it the next day, which happened to be the 4th of July. My heart sank. I told him how much I liked the boat and we started talking about CO, as that is where I had gone to college for three years. One thing lead to another and he decided to sell the boat to me if I could get him $900 cash by the next morning. That night I went to the ATM, took $500 out, another $400 in the morning and was on my way to pick up the boat at 5am sharp!

The morning was so exciting and yet also a little nerve racking for me. I had never sailed a keel boat before or even stepped foot on one. I had never navigated outside of a racecourse or Moriches Bay on the south shore of Long Island. My best friend, who is a highly competent baymen, decided to come with me for the first voyage, but he had never sailed a day in his life. To make things worse, we got to the boat and the engine throttle was seized up and I didn’t even know if it would run. I tried calling the seller but he was asleep, and considering it was 5am on a Saturday, I wasn’t surprised. There was a small amount of fog and my nerves were telling me it was going to stick around even though the forecast was saying otherwise. My girlfriend, who had driven us that morning, had never sailed before and was watching the whole situation with a worried look, wondering if she should let us two idiots sail off into the bay with a boat none of us knew would even sail properly. But the joy of buying a boat was keeping me high-spirited.

Sure enough, the fog cleared, we unfroze the throttle, and the way home was an easy straight shot through the channel. We motor sailed for about 6 hours until we got to Cupsogue Beach in Westhampton, NY where we threw anchor, headed to the beach, and enjoyed the rest of the 4th of July.

My girlfriend, who had never sailed before, got on board for the ride home that evening and fell in love immediately. I had never been so happy with a purchase in my life. She had no idea what boats normally cost and so she made a comment on how expensive it was, $900 being an outrageous amount of money for a broke college grad to be spending.

I told her that if we took the boat out the next day, each of our trips would then have cost only $450. We’ve now taken many more trips out on the boat and I can joke about how we’re probably approaching the single digit cost for each trip. We spend more than that on the beer we bring with us on the boat each time. It’s safe to say, she doesn’t think the boat was expensive anymore.


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Just rereading your tale of the sea. No one can write as well as you. I can almost smell the water. Hope you’re enjoying the work in Maine. What a beautiful part of the country you have. I heard that from my sweet Lisa. Give my love to my dear Delaney. Miss you all. Have a good day.

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