My Favorite Moments from Sailing School

How can I sum up everything that happened during sailing school, without boring everyone with the nerdy details? How about a series of vignettes that tell you all about my favorite moments from sailing school? Sounds like a plan.

I’m sure there are some of you out there that would be interested in hearing all of the technical details that I learned and loved, but not everyone. I get it. Some of us like to nerd out, while others prefer a more generic overview of something.

I’ll do my best to mix it up.

This past Christmas (2021), my mom gave me an awesome leather-bound journal with a map of the world stamped on the front. Even though leather and salt water don’t exactly mix, I brought it with me to Florida to help capture as much as possible.

The point of sailing school was to learn as much as possible about sailing, and to do as much of it as my body and the weather would allow. With my mind saturated with technical information, I was glad I remembered to throw the journal into my bag.

And I changed up the style and layout of my writing within the journal, which was probably the smartest thing ever. When most people journal, they write out what they did with little emotion behind it. I made a deliberate point of making daily lists of “things I want to remember about today,” full of emotions, dialogue, and actions.

As I look back and read some of what I wrote, I’m relieved. I didn’t remember half of those things, but I had the foresight to write them down. I’ve got them now.

Here are my favorite moments from sailing school!


Christening the boat

I’d always heard about various ceremonies held aboard boats: ceremonies for crossing the equator, christening a new boat, and the like. I had no idea that I’d be able to participate in one when I signed up for sailing school.

Within our first few hours of getting the group together, we headed out to do some provisioning for our time at sea. Our captain made sure to purchase a local bottle of rum, letting us know that we’d be christening the boat before we took off.

I was stoked. While I don’t necessarily consider myself a superstitious person, I have an open mind and believe in putting good karma, juju, vibes into the universe. Plus, it was a nice little window into the sailor mindset.

Before we turned in for the first night at the marina, we stood in a circle on the trampolines on deck with the bottle of rum. Our captain instructed us to take turns to each pour a capful of rum, raise the cap and express gratitude to the seas, then take a shot.

It was fun to watch each person overcome their feelings of silliness as we all took a turn, realizing that this was the start of a great adventure. When it came to my turn, I poured my capful and praised Poseidon and Neptune, asked for adventure and safe passage, then tossed the capful over my shoulder into the sea. Probably the top of the list of my favorite moments from sailing school, for sure.


Tall Tales Come True

Have you ever heard one of those ridiculous stories? You know, the one where the friend of a friend who knows a guy that had this insane situation happen to them? And although it’s a crazy-good story, you question the validity since it’s from a tertiary/quaternary source? As a historian, I tend to take such stories with a grain of salt.

But! I heard a tall-tale straight from the horse’s mouth, so to speak.

During our first night out on the water, we docked up at Boca Chita Key with a few of our buddy boats. Our group of 5 was onboard another catamaran, just shooting the breeze, getting to know our fellow sailing students, when their captain referenced a story about a snake getting aboard a sailboat in the area.

Of course there were the initial exclamations of disbelief, horror, shock, and wonder. Then when we pressed a little further, the captain said he heard the story from another sailor who heard it from…somewhere.

Great. Another “amazing” story that sailors could pass around, trying to flex their storytelling muscles to get a reaction from their crowd. We started wondering aloud the validity of the story and whether or not it actually happened…

Until…

Another one of our buddy boats rocked up and their captain entered. We asked Captain Jen if she’d heard the story before…and she explained that she was the captain on that fateful voyage.

WHAT???? Oh, you better believe our ears were wide open and faces were turned to hers, mouths slightly agape.

favorite moments from sailing school - moody sky above jungle island vibes
Boca Chita Key – probably where the snake is living…

Apparently there are indeed snakes that live around the southern tip of Florida, and the stories were true. In a nutshell:

Captain Jen and her students were in the middle of their sailing adventure and were docked right where we were – Boca Chita Key. 2 of the students awoke that morning and started making their coffee and breakfast, when they turned and saw a large python coiled in the corner of the boat – the boat I was currently living aboard…and in the same location!

The python appeared to be sleeping, so the students finished up quietly and went outside to figure out what to do. Once everyone woke up and quietly freaked out about the snake, Captain Jen started calling around, unsure of who could help. They didn’t want to wake it up or lose it in the ship, so someone kept an eye on it.

Captain Jen finally got ahold of Animal Services to come get the snake from the boat, and everyone was able to breathe a sigh of relief. They were then told that snakes from the Keys and other islands close by swim towards Miami. This particular python probably slithered onboard to take a much-needed nap from its long journey.

I’m so glad it didn’t happen during my time aboard!


War games

Do you remember in elementary school when we had to do math drills? And how boring that was? And then some enterprising teachers figured out that if they turned it into a game or competition, they’d get a lot more participation and even excitement doing the same thing?

I think my captain was on the same train of thought. One of the first things we learned in sailing school was how to move the boat by the power of the wind. To do that, we had to learn how to move the sails from side to side, called “tacking” and “gybing” (or sometimes “jibing”).

Instead of just having us go in some arbitrary direction, our captain thought it would be fun to play “war games” with one of our buddy boats. And to add some extra spice to the exercises, aside from the rainy weather, our captain handed us grapes to throw at the other boat as we got closer.

Picture this: 2 catamarans circling each other, trying to get as close as safely possible, while crew are constantly changing over the sails as the captains shout orders. Grapes flying everywhere. Crew laughing hysterically.

I wish I had a cameraman to capture the moment.


“Prepare to rescue”

This was a crazy one. And while it’s on my list of my favorite moments from sailing school, it’s one that I’m glad I experienced so I never have to again. Hopefully.

We were heading back towards Fort Lauderdale at the end of our adventure, taking a shortcut through the Port of Miami. After nearly getting run over by a tour operator boat (which also ended up cutting off a large ferry), we reached the mouth of the channel that opened up to the open ocean.

The waves were starting to pick up and we just finished hoisting the mainsail. As we were pulling out the jib, a monohull blew past us. He was clearly in a hurry somewhere, both sails out and engines blaring. We paid him no mind, aside from the shock at his speed as he blew past.

We were in the middle of cleaning up the lines from hoisting the sails, when the aforementioned sailboat came to a dead stop ahead of us.

His mast fell over.

favorite moments from sailing school - port of miami cranes unloading a container ship
Busy Port of Miami – before we were almost ran over

If that wasn’t enough of an alarm, the sails were in the water, filling up and getting ready to drag the boat down.

We were all in shock, and then heard our captain say words that made me choke up, for some reason – “prepare to rescue.”

O.M.G. Is this really happening? We all jumped to our stations, got the hook, some fenders and lines ready, just in case. Our captain hailed the other sailboat over the radio and asked what we could do.

One of our other students was at the helm, carefully navigating us closer to the sailboat, while compensating for the waves and swell that was entering the Port.

It turned out the sailboat didn’t need our help, as a few other guys appeared from down below and were able to help get the sails out of the water and onto the deck. They fired up their engines and headed back into the port.

Adrenaline starting to subside, we all gathered at the helm to debrief, listening to our captain lecture about the importance of having solid rigging. Seriously.


All the sea life

Let’s end this list of favorite moments from sailing school on a high, light-hearted note, shall we?

Ask most sailors what they love about being on the water and you’ll most often hear about their love of sea life. And I’ll add myself to that list.

Whether it was dolphins swimming next to our boat, or schools of flying fish following us out at sea, or a curious sea turtle coming around to say hello, I was in awe.


There’s nothing like reliving my favorite moments from sailing school! What was yours?

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