Five Welcoming Dolphins And One Mutinous Sail

Relief, a seasick cat, and the first small tests of my journey south

“Hi, buddies! There you are! You’re coming to wish me luck? That’s so nice of you.”

Yes, I always talk to dolphins.

There were five of them dancing beneath Mearr’s bow, surfacing only a few feet from where I stood. Every so often, one would launch itself completely out of the water and I’d gasp like I had never seen a dolphin before.

It happens every time and never gets old.

Dolphins and Cirque du Soleil. Those are two things that turn me instantly into a wide-eyed child.

Reaching the Atlantic brought an enormous sense of relief. The weeks of planning were over. The engine was running, the boat was moving south, and my first real solo journey aboard Mearr had begun.

I was finally moving.

Once the dolphins left, I headed back to the cockpit and started raising the sails.

I’d recently rerouted the mainsail halyard away from the cockpit because there was too much resistance in the line. Raising the sail from there had always been a pain, so I went forward and hoisted it directly from the mast instead. That’s a later problem, I thought.

It worked wonderfully.

Back in the cockpit, I rolled out the genoa. Mearr responded well. The waves were small, the breeze was comfortable, and I was getting my first chance to learn how she behaved in the ocean.

The only problem was that the wind was light.

Too light.

Before I could worry much about that, Setzer began expressing his opinion of ocean travel.

Loudly.

He was wailing and throwing up. I discovered later that he had also pooped in my bed. His Royal Highness was not pleased.

Fortunately, I’d gotten medication from the vet in case this happened. I’m very Capricorn and planner about these things. It’s the host in me. I don’t like inviting someone on an adventure without preparing for their possible gastrointestinal objections.

I gave him the medication, and he lay at my feet for a while before heading below. Soon, he was napping comfortably as though none of this had ever happened.

Now that Setzer was settled, I turned my attention back to the lack of wind.

Then I remembered. Oh yeah!

I had a sail specifically for light wind. The spinnaker.

I ran below, dragged it onto the deck, and spent the next forty-five minutes trying to rig it properly. One line would be in place, and then I’d realize it needed to pass on the other side of the railing. I’d fix that and discover the sail was tangled. Then I’d reroute another line, only to realize the first one had actually been correct and it was a completely different line that needed to change sides. All of this happened before the sail had even left the deck.

For the record, this was my first time putting it up.

Eventually, I had everything arranged well enough to raise the sail while it was still contained inside its sock. The sock keeps the spinnaker contained until you’re ready to open it and helps douse the sail when you want to bring it back down, theoretically making the whole process easier.

Moment of truth.

Drumroll.

I pulled the line to raise the sock.

It jammed. Of course it did.

I lowered everything, untangled one more thing, and prepared for take two. This time, I pulled the line and the sock rose.

Huzzah!

Oh, wait.

Not huzzah.

The entire sail was twisted.

By then, I’d been fighting with it for about an hour and fifteen minutes. This was clearly a problem for another day. I dropped the whole thing, untwisted the sail, stuffed it back into its bag, and returned it below.

Fuck this insulting sail.

Maybe we’d try again tomorrow.

There are no photos of any of this. I was too busy in a battle of wits with the sail, and I was losing.

The rest of the trip became a day of motorsailing. There still wasn’t enough wind to sail properly, but that’s how sailing goes. You use whatever the day gives you, and when it doesn’t give you quite enough, you turn on the engine.

I knew several boats from Brunswick Landing were anchored beside Cumberland Island, so I decided to join them for the night.

Cumberland is quiet and beautiful, with more than 4,000 years of human history. Much later, the Carnegie family built their mansion there, complete with an icehouse from the days before refrigeration. Ships would travel north to New England, return carrying ice, and store it so chunks could later be used in iceboxes. An engineering marvel for its time.

The island is also known for its wild horses. Some stories trace them back to Spanish explorers in the sixteenth century, although nobody seems entirely certain how the current population began.

The anchorage itself is peaceful, sheltered, and almost completely still, although a decent current moves through it as the tide changes.

More importantly, I arrived just in time for sundowners.

I dropped the dinghy into the water, climbed in, and tried to start the outboard.

Nothing.

This was the same outboard that had worked wonderfully in Brunswick.

I checked everything. Then I checked everything again. Still nothing.

Back aboard Mearr, I grabbed some tools, including a 10-millimeter socket and a ratchet wrench. I know the exact size because I’ve removed that carburetor more often than I’d like. I took it apart and cleaned it.

Again.

Afterward, the engine would run, but only if I left the choke partially on. Good enough for now.

Apparently, I was collecting an impressive number of “problems for later,” and this was only day one.

My friend Stefan from Lulu saw me fighting with it and came over in his dinghy, beer in hand, to supervise.

A vital service.

Once the outboard was functional enough to move me without paddling, I went over to their boat for dinner and a few beers.

As I prepared to leave later, I looked across the anchorage toward Mearr. My anchor light wasn’t on.

Hmm.

I was sure I’d turned it on. I guess not.

By the time I reached Mearr, it was getting dark. And it gets dark at Cumberland. There are no streetlights, buildings, or glowing marina docks. Once the sun disappears, the only lights come from the boats themselves, floating as tiny points above an otherwise black anchorage.

I hoisted the dinghy, strapped it down for departure the next day, and went to turn on the anchor light. It was already on.

Great.

Thank God for the marine electrical classes I’d taken in Annapolis. Shoutout to the Annapolis School of Seamanship!

I opened the panel and did a quick visual scan for disconnected wires. Everything looked fine, so I grabbed my multimeter. I was ready to test for power, continuity, resistance, the bulb, and even the switch itself.

Before I got that far, I moved one of the wires and noticed that something felt wrong.

It was loose. I traced it back.

You guessed it.

The anchor light.

I guess it didn’t take an electrical class to find that particular problem. What the class had given me was the confidence to open the panel, start testing, and trust that I could figure it out.

Five minutes after realizing there was a problem, I had a working anchor light again.

Relief.

And, honestly, a little pride.

The dinghy was secured. The anchor light was glowing. Setzer had returned to his usual self. The spinnaker was safely imprisoned in its bag where it could no longer hurt me.

It was past my bedtime.

Seriously.

I was getting up very early the next morning to give myself a head start toward St. Augustine.

At the time, leaving at four in the morning seemed like a perfectly reasonable idea.

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.