Twenty Feet in the Dark

Cold hands, hard sailing, and my first solo mooring in St. Augustine

At four in the morning, Cumberland Island was completely dark.

Not stars-over-the-anchorage dark. Barely seeing your hand in front of your face dark. The little white anchor lights scattered around me didn’t necessarily look like boats. They were just lights floating in blackness, and somewhere underneath each of them was presumably forty or fifty feet of fiberglass that I very much did not want to hit.

This seemed like an excellent time to leave.

There actually was some reasoning behind the 4 a.m. departure. I wanted to arrive in St. Augustine with plenty of daylight, and I wanted an incoming tide going through the inlet. That was the extent of my reasoning.

I turned on the engine and started lifting the anchor, looking around me and being completely unclear on which direction was which. I had no reference points, just a few tiny lights that I assumed were attached to boats and pitch black everywhere else.

There’s an interesting thing about my GPS, and probably most GPS units. When you aren’t moving, it has a hard time knowing which direction you’re pointing. Well, it was time to go, so I started moving in the direction I thought was right.

There was this uncomfortable stretch where I genuinely didn’t know if I was heading out of the anchorage or straight toward Cumberland Island. I needed enough speed for the GPS to finally decide which direction I was traveling. In hindsight, I could’ve just looked at the actual compass sitting there. You know. Half awake and such. When it did, turns out I was heading the literal opposite way.

Time to turn around!

I spun Mearr around and got onto my actual track. Ah. Much better.

Getting out of the anchorage became an exercise in trusting my instruments while desperately trying to make my eyes useful. The chartplotter told me where I was, and I could match the flashes and patterns from the navigational buoys ahead of me to confirm my position. The boats were another story.

At one point I passed one by maybe twenty feet. Twenty feet is plenty of room when you’re walking through a parking lot. It feels considerably less generous when you’re moving several tons of sailboat through complete darkness.

That triggered a few thoughts, mostly variations of: What the hell were you thinking leaving at 4 a.m., in pitch black, next to a national park with no lights, and then going through an anchorage? What a foolish idea.

I stared ahead like a hawk. I had my headlamp in my hand, shining it into the darkness and hoping I could catch enough reflection from a hull to know something was there, and darting from side to side, trying to spot anything as I slowly puttered forward.

Would a spotlight have been better? Of course. Did I have one? Of course not. That went onto the growing list of Equipment You Clearly Should Have Had Before Leaving.

It was November 16 and about 50 degrees outside. Fifty degrees doesn’t sound especially cold until there’s no sun, the wind is blowing, and you’re standing behind the wheel of a sailboat before dawn wearing nothing more substantial than a long-sleeve shirt and pants. I never said I was making smart decisions. That’s part of learning. Some things are just very obvious in hindsight.

My hands were freezing. Where the fuck were my gloves? More importantly, where the fuck was my jacket?

Both were somewhere below.

This is one of the less glamorous realities of sailing alone. When you realize you’re cold, there is no one to say, “Hey, can you grab my jacket while you’re down there?” There is only you, and you are currently steering the boat. In the dark.

So I nervously kept steering. I was tense the entire way out until, slowly, I started to see the world again as I veered out of the inlet and into the Atlantic Ocean.

Dawn has always felt different from the water. On land, morning arrives around you. On a boat, especially after navigating through darkness, it feels like the world is being handed back to you piece by piece. First there’s a horizon, then water, then shapes, and finally color.

The wind picked up around 10 that morning. I already had one reef in the mainsail, which turned out to be a very good decision. The wind was somewhere around twenty knots, and Mearr settled into a close reach, sometimes close hauled depending on where the wind shifted. This was going to be a sporty sail.

Once I got settled into it, I started treating it a little like a race.

There was nobody racing me. At least nobody who knew they were racing me. There was no committee boat, no starting sequence, no trophy waiting for me in St. Augustine. I simply wanted to see what Mearr could do. We’re here to have fun, right?

And by racing, I don’t mean trying to heel the boat over as far as possible and hanging on. More heel doesn’t mean more speed. At some point it actually makes the boat slower.

On my Catalina 36, the sweet spot is around fifteen degrees. That’s where the boat feels nicely balanced, with less weather helm and less drag from the rudder. So I started paying attention to the sail trim and trying to keep Mearr right around that angle as the wind changed.

I had the full 135-percent headsail out, which was a lot of sail in those conditions, and I was having a blast.

The autopilot was not.

One of the things racing had taught me was how to read the water ahead of the boat and see the gusts coming. I could start steering into them before they even reached Mearr, keeping her balanced instead of waiting for the boat to react.

I wanted to do that myself. It was too much fun feeling the boat and working with the wind. The autopilot wouldn’t have kept up anyway. It could hold a course in steadier conditions, but it couldn’t anticipate those gusts the way I could. By the time it reacted, Mearr would already be heeling harder and starting to round into the wind.

So I stayed at the wheel.

There is something about hand-steering a sailboat that is difficult to explain to someone who hasn’t done it. Eventually the boat stops feeling like a collection of mechanical parts. The pressure in the wheel means something. The angle of heel means something. The sound of water moving past the hull, the shape of the sails, the wind across your face, they all become information.

You aren’t just steering toward a number on a compass anymore. You’re steering the boat.

I did that for about four hours. By then my obliques hurt. My back hurt. Everything involved in holding myself against the heel of the boat while working the wheel had started filing complaints. I still didn’t want to give it back to the autopilot. It was useless in those conditions anyway, and I was having too much fun. Painful fun. That would not be the last time those two things went together on this trip.

There were also some practical complications with spending four hours at the wheel. For example, eventually you have to pee.

Going below wasn’t an option. Taking my attention away from the boat for that long wasn’t either. So, with one hand on the wheel, I peed into the cockpit scupper. The scupper is the drain. Basically, I peed in the sink.

There are moments in this life when I feel deeply connected to centuries of maritime tradition. This was probably not one of them.

At some point during all of this, I darted below for less than twenty seconds. I was barely inside before I heard the bilge pump come on.

That got my attention. A bilge pump running on a sailboat is not automatically an emergency. It does, however, immediately raise one fairly important question: Why?

I was a little worried, not terribly. Mearr had been heeled over and moving around quite a bit, and there is normally some water sitting in the bilge. I figured it could simply be sloshing around enough to trigger the pump. I made a mental note and was back at the wheel almost immediately.

Meanwhile, Setzer was having a much worse day than I was.

His cries from below were heartbreaking. He was seasick, scared and upset, and at one point I actually heard him throw up.

And I couldn’t go help him.

I had seasickness medication for him onboard. I had even given it to him before we sailed the day before.

That morning, I forgot.

That was on me, and I felt terrible about it.

I could step away from the wheel for a few seconds if I needed to, but I couldn’t go below long enough to get the medication and give it to him. With the wind up and Mearr moving the way she was, I needed to stay at the helm.

So I listened to my little boy crying and knew there wasn’t much I could do for him at that point. He ended up throwing up several times.

There was no chance I was forgetting his medication before the next sail.

While all of that was happening below, I was outside having my first truly exhilarating sail on Mearr. I was having an amazing day. Setzer very much wasn’t.

Eventually, after hours of wind, hand-steering and concentration, St. Augustine appeared ahead.

I had been through this inlet many times before, and that familiarity helped. Some people find St. Augustine tricky. I already knew it, and there was something reassuring about that. Apparently I was learning something from all those previous trips.

I called the marina and confirmed my mooring assignment, then radioed the Bridge of Lions for the next opening. After that, there wasn’t much to do except wait, so I chilled.

That’s when the fatigue really arrived. Not just being tired, but the awareness of how different this was from every delivery I had done as crew.

When you’re crew, even on a long day, there are other people aboard. Someone else can steer and navigate. Someone else can notice something or make a decision. This was different. It was partly leisure sailing, and it was also work.

All day I had been sailing the boat, navigating, watching traffic, trimming sails, steering, troubleshooting, making decisions and staying alert because there wasn’t anyone else there to do any of it. I was only two days into the trip, and I was realizing how tiring that could be.

That was good information. Fatigue is when mistakes happen, and sailing alone meant I couldn’t afford too many of those. I wanted to get all the way to the Keys in roughly two weeks while only sailing during daylight. I was learning that doing it would take more out of me than I had expected, and I needed to understand how hard I could push myself without crossing that line.

The Bridge of Lions finally opened, and I motored through into the south mooring field. There was just one more thing to do: pick up a mooring ball alone. I had never done that before.

With another person, picking up a mooring is straightforward enough. One person drives the boat while the other stands at the bow with a boat hook. You approach slowly, grab the pennant, run your line through it and secure the boat.

Alone, I was both people, which is inconvenient because the helm and the bow of a Catalina 36 are not located in the same place. Shocker.

Luckily, I had thought about this ahead of time. I had spliced some long mooring lines that could reach all the way back to the cockpit. My plan was to bring the mooring ball alongside near the cockpit, leave the wheel, grab the pennant, run my line through it, then walk the line forward and secure it at the bow before Mearr drifted away.

Simple. In theory.

The first attempt was not great.

Wind and current were pushing in different directions, which makes judging what the boat is going to do considerably more challenging. I got close to the ball, then by the time I tried to grab it, Mearr was already drifting toward the neighboring catamaran.

Abort! Forward, full throttle!

I got away from the catamaran and regrouped. Okay. That did not go well at all.

I was already nervous about trying this alone for the first time. Nearly introducing Mearr to the boat next door was not how I wanted to end a journey that had barely started. At least now I knew a little more about what the wind and current were doing.

I lined up again, changed the approach slightly and adjusted my speed. The second attempt went flawlessly. I brought Mearr alongside the ball, grabbed the pennant, ran the line through, walked it forward and secured it.

I did that? Huh. That was cool.

Then came the pride. Not because picking up a floating rope is some enormous accomplishment. From the outside, some of the things that feel significant in sailing probably look absurdly small. You grabbed a rope. Congratulations.

Except that wasn’t really what had happened.

That morning I had left an anchorage in complete darkness by myself. I had gone the wrong direction, corrected it, navigated my way out, sailed Mearr hard in twenty knots of wind, spent hours hand-steering, dealt with a mysteriously active bilge pump and listened helplessly while my seasick cat threw up below. Then I entered St. Augustine and picked up my first mooring ball alone.

I had surprised myself again.

That feeling would matter throughout this trip. I wasn’t suddenly less afraid of things going wrong. What was starting to change was how much I trusted myself when they did.

Once I was secure, I gave the bilge a quick check too. Nothing looked horribly wrong. There was no obvious influx of water or immediate reason for concern, so I chalked it up to the boat moving around.

Of course, opening the companionway brought me immediately back down to earth.

The boat was a disaster. Apparently many of the things I had previously classified as “secured” were, in fact, not secured. There was shit everywhere.

And then there was actual shit. On my bed.

Setzer had pooped there sometime during the passage. I was exhausted, so there was definitely some weariness and annoyance in my reaction. Seriously? One more thing?

Then I looked at him.

He’d spent the day seasick. He had been crying. He’d thrown up several times. He’d been scared and miserable while everything around him moved in ways he didn’t understand.

Poor little boy.

Somehow, now that we’d stopped moving, he was completely fine. Not recovering. Not hiding. Fine. He jumped out onto the deck and chilled outside, being his usual self.

Apparently his horrible day was over. Meanwhile, I felt like I had been run through a washing machine.

Adventure is funny that way. From a distance, solo sailing sounds like freedom. Wind in the sails. Open water. A person and their boat making their way down the coast. And sometimes it absolutely feels like that.

Sometimes it feels like doing something you weren’t entirely sure you could do, then looking around afterward and thinking, I did that?

Other times you’re freezing because your jacket is below, your bilge pump has mysteriously turned itself on, your back hurts, you’re peeing into a scupper, everything you own is on the cabin floor and your cat has shit in your bed.

All these things are true.

Eventually I headed ashore to check in with the marina and get the keycard for the showers. By then, the fatigue I had noticed while waiting at the Bridge of Lions had fully settled in. I had originally planned to leave again the next day, but standing there after everything that day had taken out of me, I decided to stay another night.

It wasn’t a difficult decision. I love St. Augustine, and clearly I could use the break.

I also wanted more time to deal with the outboard. It was running again at Cumberland after cleaning the carburetor, but still wasn’t right. It would only run with the choke partially on. That had been enough to keep the trip moving, but my dinghy was basically my car while cruising. I wanted to spend some time figuring out what was actually happening before heading farther south.

So St. Augustine became a two-night stop.

Then I took a hot shower. That gift from the Gods. For a few minutes, I could finally let everything go.

I went to Pizza Time for dinner, because I’m only human. It also has a special place in my heart because of all the memories I have there with Captain Dave. After a day of cold, wind, adrenaline, hand-steering, mooring balls, and a mess to clean up, hot pizza sounded incredible.

By around eight o’clock, I was completely done.

I had started the day in darkness at Cumberland Island, barely able to see beyond the glow of my instruments and a scattering of anchor lights. I ended it safely attached to a mooring in St. Augustine. 

Somewhere between the two, I had become just a little more capable of doing this alone.

Author’s Note: This story took place in November 2025. It was originally shared as a short social media post and has been expanded here with the benefit of hindsight.