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  • Tristan Sess

Round One

We did it! The first overnight passage was a success. Although we set out to make it to Block Island and we never did, we had such a great time along the way.

The trip started off rocky, I’ll be the first to admit it, mostly my fault, but nothing that really affected the trip too much. I forgot the portable stove we had been planning on taking for our breakfasts and a dinner on the way. Even with the small swells we had during the trip, we realized just how difficult cooking would have been even if we did have the stove, so fortunately that didn’t affect anything. The next obstacle in my way was one I had no control over. Worse than any storm the ocean could brew up, there was no avoiding my fate, NYC weekend traffic. I ended up getting home around 7:00, about two hours later than anticipated, but neither the missing stove or the bumper-to-bumper traffic were going to slow me down. We left the dock at 7:30 and were on our way to Block Island.

I mentioned in an earlier post about how I wanted to get the boat out on the water at least a week in advance and test it out as well as explore the inlet. Unfortunately, due to timing and weather, that never happened, so we had to do everything for the first time that night. As the sun was setting, we approached the inlet and it was perfect. No real boat traffic, no swell, no strong currents, and the engine was running just fine (especially considering I put far too much oil in the gas). For me, we had already succeeded. We left the dock and were officially at sea. As easy as it can sometimes feel in the moment, a lot of preparation went into what we were doing and few people ever make it as far as we had, sailing in the ocean with a destination over 75 miles away.

As the sun began to go down, I briefed everyone on what we could do for watch rotations and how to sail downwind through the night, as well as how to operate the GPS navigation. We decided to do two person watches from 10-2 / 2-6 / 6-10. My girlfriend, Delaney, and I took the first watch and although entirely dark, with no autopilot and a rolling boat, I was in heaven. I was doing what I loved with the people I loved. Delaney had never been out at sea other than for a brief one-hour fishing stint and began to get sea sick. Despite being in the fetal position about 90% of the time, she was quite the trooper and managed to stay on deck with me the whole four hours.

She, like myself, understand and have a deep love for type two fun. In case you don’t know what that is, it’s when you experience an event that most certainly isn’t fun in the moment but in hindsight, is what you wanted all along. Camping in the cold, hiking in the rain, any real adventurer knows what I’m talking about, even if you have another name for it. There are so many ways for people to explore the world and often times the best, and most enthralling ways to experience adventure are actually more miserable than fun. I often tell people that one of the most fun times I’ve had on a sailboat was in the pouring rain in the middle of the night in sweats. Sounds fun right! Without digressing too much, just know that sailing is one of the most beautiful things I know of in this world but anyone that tries to glamorize it and make it seem as if you can have all the fun with no effort is lying…. or the just have way more money than I do and can pay up.

The next day we ended up making a crew decision that rather than complete the entire journey to Block Island and have no real time to stop, we would divert from our course and head north around Montauk Point and spend the afternoon in Montauk. Was I a little disappointed, of course, but I tried to make the best decision I could for everyone involved. What fun is a trip if you’re the only one having fun.

We dropped anchor in Montauk Lake and tunned in to the radio to verify there was a free place to keep our dingy after we shuttled in two at a time on our tiny blow-up inflatable. The first call we heard was from someone asking for assistance in bringing their mega yacht into the harbor and what the best approach was, strictly business. Then me, “Gurney’s harbor master, Gurney’s harbor master, this is the sailing vessel Jonny Longshaft checking in to make sure we can keep our raft at the dock for free for a couple of hours, over.” I would say, equally, if not a more important call than that of which preceded mine.

After a nice lunch, some cruising around town, our uber breaking down and a power nap, we made our way back out to sea. That night we all slept better, not because we were use to it, but because we were exhausted. Generally, three-day trips like ours are the most difficult because your body doesn’t have time to get use to the watch cycles and it’s still long enough to take all of the life out of you. Typically, single overnighters and five-day trips are easier, or so I’ve heard. That night was much clearer and Delaney didn’t get sick. As tired as you can get at the helm, there are few things more tranquil than watching the sun rise over the horizon while under sail. It’s so quiet, all you hear is the sound of the wave on the side of the boat. A little chilly and blindingly bright. We planned this trip so that Delaney could join us because she leaves for Colorado for a few months to complete an internship and I won’t be able to see her for all that time. Sitting in the cockpit, with the bright orange sky and complete calm that seems so hard to find anymore, it was the perfect way to spend some of our last hours together.

After the trip came to an end and we got home, we had sailed (and motored) just over 130NM in about two 18hr jumps. A few of my classmates asked me about the trip on Monday when I got back and I told them all about it. When we first decided to change course, I’ll admit, I was disappointed. Block Island was literally in sight as we passed the Montauk Light House and every part of me wanted to keep going. I can’t be upset though, I had just done something so big compared to anything I had ever done before and rather than harp on 40 extra miles not sailed, I was easy for me to cherish the first big sailing trip of my life. We didn’t make it to Block Island but it’s not going anywhere, now at least I have a good excuse to do it again.


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Elizabeth Pitman
Elizabeth Pitman
May 28, 2021

Your individual pics showing each step of the way is truly epic. You are a master of the word. I absolutely love reading your posts, your love of sailing. I can almost smell the water.


May 24, 2021

Sounds like an amazing time, can’t wait to tune in for more. -Eric B

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