Sailing Misadventures, and The 3 Rules of Sailing

According to my Gramps, there are three basic rules of sailing:


1: Keep the people in the boat.

2: Keep the water out of the boat.

3: Don’t get lost or run into anything. 


Yesterday, due to a rather unfortunate series of events, Gabe and I managed to fail at two of the above. Let me just say, there are some adventures that I could experience time and time again, and then there’s others that… well… I think I’ll pass on replaying this particular episode EVER again.

I’ve been around boats ever since I was a baby. Gramps has a fascination with them and owns more than a few canoes, rowboats, outboard motorboats, and sailboats. My uncle circumnavigated the world when I was younger, and my dad dreams of getting a boat someday and cruising for a few years. As such, the boys and I have had ample time to fool around on the water in whatever boat happens to be out and ready to go here on Wolfe Island. Gramps built us our own (exceedingly wide and sturdy) rowboat when I was maybe nine, and that boat introduced us to the concept of exploring the local canals on our own as pirates or vikings. A few years later, we all took a couple of summers worth of sailing lessons. So when Gabe and I decided to take the little four-person sailboat out for a quiet cruise yesterday morning, no one had the least worry that we’d make it back fine.

Gabe motored us down the canal to the dock where Blue Duck was moored, chatting cheerfully about his time in Indiana, waterparks with cousins, and Ezra’s many misadventures since I’d been gone. We left our shoes at the dock, stowing a water bottle and a spare life jacket up in the tiny compartment in the bow, and rigged up the jib sail. Blue Duck is intended for three or four people, five in a pinch. It’s perfect for tooling around the bay in, so long as the weather isn’t too rough. Gabe opened the hatch in the stern of the boat and groaned. “The self-bailing system.”  He tossed me a bucket. “The stupid thing’s broken. Instead of bailing, it keeps letting water into the inside of the boat. The cork’s fallen out again.” Replacing the cork, he began to bail. It took no less than half an hour to empty the boat out. Rule 2 attended to, we sailed out of the canal and into the bay.

For a while, it was smooth sailing. Gabe rigged up the mainsail, and with an excellent winding blowing across the island, we were soon speeding out of the bay and into the shipping channel towards New York. Gabe took over the position of skipper, and as the wind started to pick up and the waves grew larger, he decided it’d be a great idea to scare the crap out of me.

It’s pretty well known that of the two of us, I am more likely to be cautious on the water (I have a ridiculous fear of open water in general) and Gabe is more likely to take chances. However, Gabe’s also more likely to pull off risky stunts, whereas if I try something stupid it ends in precisely the way Dad said it would. Go figure.

The boat heeled way over multiple times, bouncing over the waves at a tremendous speed, Gabe laughing like a maniac and me caught somewhere between an adrenaline rush and being completely paralyzed by the thought that it was entirely possible that we’d flip over. It was one of those situations where you find yourself wanting to plead for the sibling in question to stop, at all costs, but don’t want to come across as a total sissy.

Pathetically, I went with being a total sissy, and resorted to pleading. 

We’d turned around by this time, heading out of U.S. waters and back towards Wolfe Island. As we passed the point of Carlton Island, Gabe agreed to slack off a bit, and the boat evened out. Unfortunately, he was just a bit too late. As he started to ease tension on the mainsail, a huge gust of wind hit us. In horror, I saw the far side of the deck plunge into the water, which I might add was completely black, due to the clouds above and the sheer amount of water below. Gabe let out a shriek and got half an expletive out before he fell off the boat and disappeared as the boat began to roll on top of him. My panic served me rather well. Somehow, as the boat rolled, I managed to stay on top of it. Clambering over the side, I found myself standing on the daggerboard, the boat completely sideways. It began to roll upside down, the sails being dragged under by the currents. I looked around frantically for Gabe. He hadn’t been wearing his life jacket, so for all I knew, he could have been knocked on the head and at that very moment be drifting to the bottom. Not so. A moment later, he erupted from a wave which nearly swamped the boat, still letting out a steady stream of expletives interrupted by a good deal of spitting and coughing. I don’t think I’ve ever been so relieved to see somebody.

An emotion which was quickly replaced by annoyance and complete hysteria when he reached up, spluttering, and accidentally folded the daggerboard into the boat, sending me plunging into the waves and letting the boat finally roll belly up.

I’m a wimp when it comes to situations like this. I hate open water, huge waves scare me, and if it’s terribly deep I’m not likely to want to swim. And yet I love boats. It’s a sad irony. Plunged beneath the surface, I was fool enough to open my eyes and see the seemingly endless black all around me. The boat had a nightmarish look about it. Suspended upside down in the clear dark water, lines snaking out to tangle around the masts, each other, and my feet, sails reflecting the light eerily as they rippled uselessly beneath me… She looked like a ghost ship, abandoned in an underwater world, defying physics completely. I lost my mind for about a full minute, and didn’t regain it until I was safely up on the belly of the boat. Gabe fished our life jackets out of the bow and we sat, panting, staring at each other in shock.

The boat gave a loud gurgle and settled deeper into the water. The cork, I remembered, coming to my senses. The self-bailing system with the faulty cork. A steady fizzling was coming from beneath us as the boat steadily filled up. It was my turn to swear. Our boat was sinking. The nearest land point was far enough that swimming could take a good long while, the currents were strong, there was absolutely no way we’d be able to get the boat up on our own… and we had both started shaking uncontrollably. The cold was pretty unbearable.

The good news was that Blue Duck was taking her time about sinking. I guessed we’d have about forty minutes to an hour at the rate she was going down, and Gabe pessimistically wagered on a half hour. I think at that point he was more worried about what would happen if we lived through this, the boat sank, and he had to face Gramps, than he was about our actual chances of survival.

My hands had gone completely numb by this time, and our voices were hoarse from shouting at the closest island. The boat was making the occasional large glugging noise now, and had settled much deeper into the water. I’d taken off my life jacket and was waving it rather desperately, when on the distant shore I saw three small specks running towards a dock.

Within about ten minutes, Gabe and I were safely on board the posh boat of a extremely fantastic family who was summering on Carlton Island, and Blue Duck’s bow was secured to their boat by means of a spare line. I borrowed a phone and called Dad. Incoherently, “Dad! Whew. Hi. Uh. The boat. It’s sinking. We’re sinking the boat. But we’re ok! But it’s sinking. Uh. Erm. Carlton Island. Right.” And then, somehow, the boat righted itself behind us. Phone forgotten, I began shouting at the woman on the tiller to KEEP THE BOAT MOVING. Five minutes and multiple, multiple swear words later (it kept coming dangerously close to capsizing again), I realized my Dad was still on the phone… having heard all of that… oops.

He and Gramps arrived later on, ironically, after we had the situation under control. The boat was righted, bailed out, the cork replaced, and Dad and Gabe sailed it home. The weather had cleared up entirely, leaving them with perfect skies and a mild swell to deal with on the way back. Gramps has instructed me to mention his unbelievably fantastic boat handling, good looks, and heroic rescue of a fair maiden, namely myself. Gabe he made sail home instead of towing him, and that was all that was said about it. He also made a point of towing both my highly penitent sibling and my mildly displeased father out into the shipping canal and releasing them there just as a freighter cruised through… Yikes.

The one redeeming factor of this particular misadventure was that we managed not to break Rule 3. We knew precisely where we were. Also, we saved the boat, managed not to get ourselves killed, and made some new friends on Carlton Island. By popular vote, the morals of the story are these:


Lose your head. You’ll feel better afterwards.


Know when to drop the mainsail.


Testosterone poisoning should not be used for onboard entertainment. 


Never laugh at the 3 Rules of Sailing. They’ll come back to bite/drown you.


Getting the boat bailed out again.
Getting the boat bailed out again.
Towing Blue Duck out from Carlton Island. The weather was perfect now, of course.
Towing Blue Duck out from Carlton Island. The weather was perfect now, of course.
Gramps, demonstrating his expert boat handling and fine looks.
Gramps, demonstrating his expert boat handling and fine looks.


Back to Wolfe Island!
Back to Wolfe Island!

7 Replies to “Sailing Misadventures, and The 3 Rules of Sailing”

  1. AAAAActually we were trying to play Jack Sparrow and get to the Dead mans chest… All part of a lovely plan…

  2. Yikes! I’d be pretty nervous too and I think the expletives may be way over the level you got to:) Glad all turned out OK, always a lesson to take from every situation, right?!

  3. THIS! This is why I stay on dry land. Omgosh I would have sworn as much or more than bohemiantravelers. I’m sure together we could have reached new levels of expletives only read about in pirate novels. I’m so glad everything turned out okay. Really though, can you just have some good luck for a spell?

  4. It’s funny how your dad and bro are wearing life jackets, securely fastened, on the way back to Wolfe Island!

  5. Holy Crap! So glad you both are safe. Surely you have enough awesome stories without having to do stuff like this to create new ones? lol

  6. Oh my gosh. I JUST told Gabe about our harrowing first-time-sailing. Wasn’t this harrowing though. The ocean is a frightening beast and I’m so glad you guys are safe.

  7. […] way to end my nineteenth birthday. For the record, this is the first time since Gabe nearly sent us to the bottom of Lake Ontario that I’ve set foot in a sailboat with him. “That’s never going to […]

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