A Tiny Plastic Datil Pepper That Meant Something Important

I woke up the next morning feeling like a completely different person. The difference was almost ridiculous. The night before, I could barely function. A night of sleep later, I felt fully restored. That was encouraging all by itself. Maybe yesterday hadn’t taken as much out of me as I thought.

There was just a little bit of dawn starting outside. Setzer was back to being Setzer. I fed him, opened the hatch, and he immediately wanted to go outside. He wandered onto the deck while I made coffee, and the two of us sat there watching the sun come up over Anastasia Island.

The water was calm, although in St. Augustine it never really stops moving. There is always current running through the mooring field. Boats surrounded us, including the catamaran I had nearly introduced Mearr to the evening before. I heard the horn at the Bridge of Lions announce the first opening of the day. Otherwise, it was quiet, and I had nowhere I needed to be.

There is something strange about sunrises. You could probably describe most of them using the same handful of words: orange horizon, changing sky, light reflecting off the water. Yet somehow, no two feel the same. I think it’s because you never arrive at a sunrise empty. You bring whatever happened yesterday, whatever you’re hoping for today, the things you’re excited about and the things that scare you.

Then the light starts coming in, and something wakes up with it. Your mind, your body, your plans. The fears and doubts can still be there, but somehow the day starts feeling more possible.

This sunrise had a lot wrapped up in it. I was in St. Augustine, a place I already loved, for the first time on my own boat. Setzer was beside me, the cat I had always imagined having with me for this life. Cumberland Island was behind me. After months of wondering whether I would ever actually leave Brunswick, worrying that Mearr and I might become permanent dock queens, and finding one reason after another to delay just a little longer, I wasn’t preparing for the journey anymore.

Holy shit. I was actually doing this.

Somewhere in there, confidence was beginning to replace some of the fear. Not all of it. Not even close. Just enough that when my brain eventually turned toward the day ahead, I wasn’t wondering whether I could keep going. I was thinking about what needed doing next.

First up: the dinghy outboard. At Cumberland Island, I had managed to get it running. Kind of. Running only with the choke cracked meant the fuel-air balance was off somewhere. I was pretty sure fuel was the culprit, so back into the carburetor I went. Not because taking apart and cleaning a carburetor was my idea of a relaxing morning in St. Augustine, but because if I needed parts, I wanted to know before I headed into town. Then I could make an errand part of the day instead of discovering at four o’clock that I needed something from a store somewhere else.

So I pulled the carburetor apart again. This time, I had two important things I hadn’t had at Cumberland Island: daylight and time. I could actually see what I was doing.

I took the carb apart properly, cleaned everything again, and took my sweet time doing it. The fuel got drained and I made myself a makeshift filter and water separator to make sure there wasn’t water in the gas. I also replaced the fuel line because I already had another one aboard and had been meaning to change it anyway.

This is where my troubleshooting methodology became slightly questionable. I changed several things at once, which meant that when I put everything back together and the engine fired up beautifully, I had absolutely no idea which one had fixed it. Lesson one: I solved the problem. Lesson two: maybe change one variable at a time next time.

Still, when that little engine sat there purring away, I had a definite fuck-yes moment, followed immediately by cautious optimism. I didn’t trust it yet. I took the dinghy out near the bridge and zipped around for a while. Everything ran perfectly. I brought it back to Mearr, shut the engine off, let it sit, and tried again.

It started right up. No parts needed. Dobby was freeee!!!

I loaded my electric scooter into the dinghy and headed for shore. I didn’t really have an itinerary. There were things I wanted to do, although I wasn’t interested in turning my day off into another schedule. I had eaten breakfast on the boat, so food wasn’t urgent. Visiting the distillery and a hot sauce shop were top of the list. Beyond that, I would decide as I went.

The scooter was perfect for St. Augustine. The distillery isn’t terribly far from the marina, although riding there was considerably more fun than walking. I went in for the self-guided tour and tasting. 11 a.m. is the perfect time to start drinking, doncha think?

I had gone there hoping for rum. Rum is usually one of my favorites, and I was excited about bringing back a bottle made in St. Augustine. It fell flat for me, which was disappointing. Thankfully, they redeemed themselves with the bourbon and their new world gin.

The gin was really good, and they had a tonic mixer that made sense on the boat. It was small, easy to store, and all I had to do was add some SodaStream sparkling water. I could make myself a nice drink without filling a locker with bottles. I had gone looking for rum and somehow came home with gin. Seems about right.

Somewhere in my wandering, I made it to one of St. Augustine’s hot sauce shops. If you like spicy food and somehow manage to visit St. Augustine without encountering a Datil pepper product, I’m not sure you actually visited St. Augustine. They’re everywhere.

Datil peppers aren’t even necessarily my favorite pepper. I wanted them because they belonged to the place. There is something I love about bringing home something local, something that connects what I’m eating or drinking to where I found it.

I bought a few hot sauces, some Datil pepper rub and a bottle of Datil pepper vinegar. The owner was working the shop that morning and nobody else was there yet, so I hung around for a while talking with him and tasting entirely too many hot sauces. Eventually I had to remind myself that everything I bought had to live on a sailboat, I had to actually eat it, and I was heading toward the Keys where I was already expecting to spend plenty of money. Self-control prevailed. Mostly.

There was one thing I wasn’t leaving without. Hanging from the bottle of Datil pepper vinegar was a tiny plastic pepper, maybe three-quarters of an inch long. I wanted the pepper more than I wanted the vinegar.

There is a wooden post right in the middle of Mearr’s cabin. Hanging from it are a handful of little things that probably look like random trinkets to anyone else. They aren’t. There’s a seal claw from Canada, a tiny dolphin given to me by friends, a small dream catcher, two crosses representing different parts of my life even though I’m not religious, and a little metal wave with a saying on it that a special friend gave me before I left for the Keys. It’s a bit like magnets on a refrigerator. Every one of them means something to me.

That tiny Datil pepper belonged there.

St. Augustine has always done something to me that I can’t really explain. I talk a lot about home being a feeling rather than a place. There have been three places in my life where I arrived for the first time and immediately felt that feeling: Kelowna in Canada, Florence in Italy, and St. Augustine. Why? I have no idea. I’ve learned not to dismiss a feeling just because I can’t explain it logically. Feelings are information too. They often tell me something before my brain has figured out why.

Of the three, St. Augustine makes the least logical sense. Objectively, it’s a tourist town. Yet the first time I arrived there, before I had any history with it, something in me recognized it as home. Since then, the place has accumulated stories.

It’s where I met John and Kym. It’s part of how I learned more about sailing. There are memories of coming through that inlet at night and baking bread offshore in the Atlantic. Every visit seems to add another layer to whatever connection started before I had any reason for it. I’ve stopped questioning feelings like that. I trust them.

So when I saw that ridiculous little plastic pepper, I knew exactly what it was: a tiny piece of St. Augustine I could carry with me. It earned its place on that post before I even bought the bottle of vinegar it was attached to.

While walking through town, I ran into Dave and Mary Roth from Brunswick Landing completely by chance. Earlier, I had also found Elizabeth and Patrick from Southern Sassy at the dock. Their boat was having generator issues and they were trying to figure out what came next for them. Southern Sassy was being very sassy.

I had sailed away from Brunswick and somehow Brunswick kept showing up. Are y’all stalking me? Yet that was also one of the things I was beginning to love about the sailing community as a whole. Everybody moves. Boats scatter in different directions, people come and go, and somehow you keep crossing paths again. Community doesn’t disappear when you leave the dock. It moves with you.

That evening I had dinner with Patrick and Elizabeth somewhere near the marina. I don’t remember the restaurant. I remember the company. We caught up, talked boats, talked about their generator and what they might do next. Normal cruising conversation, really. How are you? Good. Something broke.

After dinner, I wasn’t ready to go back to Mearr yet. St. Augustine was glowing for Christmas. This was my second time seeing it like this. The first had been three years earlier, in December 2022, when I helped Captain Dave move his boat back to Titusville.

The lights are a whole thing here. Buildings outlined in white, palm trees wrapped from the ground up, streets glowing, people everywhere just taking it in. There was something playful and nostalgic about walking through it. You could feel the energy from everyone else enjoying it too.

It was also a little romantic. Couples walking together, people taking pictures, families stopping under the lights. There was something about the whole atmosphere that made you want to share it with someone.

I made my way down to Auggie’s Draft Room and had a couple beers. They were setting up a snow machine outside because apparently palm trees and Christmas lights weren’t quite enough. That night happened to be their first test.

Suddenly there was fake snow flying through the middle of St. Augustine. Kids were running through it, people were taking pictures, everyone was laughing. It was ridiculous and wonderful and exactly the kind of thing I was happy to stumble into.

Would I have preferred to have someone standing beside me? Absolutely. There are plenty of moments on this trip I would have loved to share with someone. That didn’t make this one less worthwhile. I stood there and enjoyed it, knowing that tomorrow I would be back on the watery road, heading south. That night I got snow in Florida.

On the dinghy ride back to Mearr, I still wasn’t quite ready to let St. Augustine go. From the water, the whole waterfront was glowing against the dark sky. I pulled up to an empty mooring ball, tied the dinghy off and sat there long enough to take a few pictures. I wanted a picture from this trip. Not just St. Augustine lit up for Christmas, but St. Augustine as I was seeing it this time, from my own dinghy, on my way back to my own boat.

Then I untied and headed back to Mearr, and my brain started shifting toward tomorrow. I wanted to do as much as possible that night while I still felt good: check the engine, make sure the dinghy was secured properly, put things away, make the morning easier on myself.

I didn’t even know exactly where I was going the next day. There were plenty of possibilities. Weather would have a say. So would the tides. It all depended on what time I happened to wake up. I wasn’t in a rush. I had looked at the tides enough to know I would probably take the Intracoastal Waterway, although I could make that decision in the morning. It was going to be a seat-of-my-pants kind of day.

This hadn’t been a wasted day in St. Augustine. Quite the opposite. I had fixed the dinghy, taken care of Mearr, and taken care of myself. That last one mattered just as much. I had limited time to get to the Keys, but if the whole trip became nothing more than getting there, I’d be missing the point.

In barely a couple of days, I’d already had plenty of moments where I was genuinely worried. And each time, I kept reaching into things I had learned over the previous few years and finding something useful. As corny as it sounds, I remember thinking, I feel like a fucking badass.

Not because I wasn’t scared. I was. That was the whole fucking point. The Keys were the destination. Challenging the fear, trusting myself, and moving anyway was the point of the trip.

It connected to a question I had carried with me even before leaving Brunswick: What would you do if no one was watching?

For me, it has always been a question about integrity. If nobody sees the choice, applauds the effort, or knows what happened, do I still show up as the person I say I want to be? Sometimes I do. Sometimes I absolutely don’t. That’s okay. I just want to choose that version of myself more often.

I went to bed proud, inspired, and still a little anxious about tomorrow. That felt about right.

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.