Integrating AI into the Cruising Lifestyle
Fatty Goodlander explores sailing with AI, blending tech, travel, and laugh-out-loud misadventures in this edgy, irreverent cruising column.
Damn! AI (Artificial Intelligence) is smart and very quick. I purchased an AI unit for my boat and it immediately yelled to my wife as I carried it aboard, “…divorce the bastard!”
Even more amazing, it is location-specific because of its internal ‘location services’ feature, so the AI spoke aloud in a drunken West Indian accent (because, I assume, we were booze-cruising the Lesser Antilles at the time).
…how apropos!
This new AI interfaces with my chart plotter as well. Almost immediately, I noticed the difference. “Yo, mudderrunt—what’s your pleasure? Hit a rock or a reef? Get run over by a ferry or a freighter or—no charge for the gratuitous violence—the cut-throat crew of a blood-thirsty drug boat fresh from Santa Marta?”
Yes, this AI unit does far more than I anticipated. Thus, when I innocently approached my cockpit mainsheet winch, alarm bells rang and a hidden speaker announced that such machinery should only be operated by a sailor that knew proper mainsail trim within a ‘meter or two.’
…that eliminated me.
I have two locations for my mainsail boom—centerline and flapping.
With the newer AI firmware, you no longer have to say, “Hey Siri” or “Alexa”—as the trigger phrase can be custom-programed. For example, mine actuates with the phrase “Let’s f*#&!” while my wife’s responds to “Men are Such Jerks!”
…yeah, gender-sensitive—sea gypsy-style.
Huge advances have been made in the context of a situation. For example, if my better half is at the helm, AI mutters nothing save an occasional, “…atta gurl!” However, if I’m at the helm it asks me important, pertinent, specific questions such as, are you aware your leeway exceeds your forward boat speed?
Of course I am—what does it take me for, a fool?
The AI really comes into its own while stern-to in the Med. To save time, it asks every random stranger strolling down the dock how much it should pay them. (The Med ain’t free, I’ll tell you dat, me son!)
That’s right—these LLM units analyze a wide and diverse array of data. If they determine that the skipper is cheating on his wife, likes to kill fish for no apparent reason, has a pot belly, prefers bright-colored golfing togs, likes to pay double, and drinks scotch instead of rum—these units automatically cut back on their internal processing power. Why needlessly waste 12-volts on a stinkpotter?
All the bareboats in the BVI are now using AI. There’s even a function that allows a charter skipper to pre-determine the speed by which they’ll eventually drag!
Useful!
But, honestly? I no longer automatically belittle bareboaters—not since I informed the un-tanned crew of an OutHouse 41 that they were attempting to anchor in five-hundred feet of water off French Cap—and they curtly replied, “That’s all right, we only draw four!”
The most sophisticated AI units are even developing a wicked sense of humor. For example; When in bilge-alarm mode aboard a carvel-planked wooden boat, they don’t just beep, they yell rude stuff like, “…more leaks than the White House! …more flow-through than a spaghetti colander… more dribbles than the Old Man’s bladder!”
…perceptive, right?
…and kinda fun, in a slightly-too-graphic way. For example, when my wife queried my AI assistant about my dress-shirt size, the very well-informed LLM not only mentioned by neck measurement—but tossed in the fun-fact that my neck size and my IQ happened to be the same number!
All the units now sport a ‘gender selection’ option as well. This section is huge since it caters to an outspoken group that self-identifies with nearly all the capital letters in the alphabet.
Speaking of sexism and sailors, I’m ashamed to admit that my AI language settings favor such nouns as large tophampers and curvaceous transoms—okay, so I’m old-fashioned.
But my wife claims that elderly female coyotes aren’t much different. Recently, she was sailing with a female skipper and, while docking, she briefly tried on the “Lady Skipper” version of the Apple Pro Vision Marine goggles that were sitting near the helm station. And as the young, handsome, muscular fuel jockey came aboard with a long diesel hose, the AI unit in the Vision Pro muttered, “Nice package!” but when I stepped aboard it dismissed me with, “…built like a gerbil.”
…talk about ego-bruising!
There are even units hopeful gold-diggers use as they stroll the Cowpet Bay beach during St. Thomas’ annual regatta. Early versions merely estimated overall wealth, but newer models hit on a wide variety of sugar daddies—but primarily focus on gullible, overweight ones with developing heart problems!
Nice—and time-saving, too!
…I mean, the last thing a gold-digger wants is to marry an ugly, tight-fisted centenarian with a pocketful of azure pills!
Believe it or not, AI can even anticipate costly situations developing while offshore! I mean, why lend a brand-new, expensive PFD to an idiot with a propensity for falling overboard—on a windy, rough night crossing the Anegada?
…commonsense, right?
I actually carry a PFD filled with bricks instead of buoyant kapok—that I can toss to any American MOB/SOB that stupidly made a lot of jokes about suing people prior in the passage.
And this whole kerfuffle about pronouns is crazy—I’ll be damned if I’m going to insult a female crew member that has exercised her ERA option to go night-swimming… during a full gale off the Cape of Good Hope on a moonless evening… insult her by tossing her an M-O-B pole. No siree—I’m a little too gender-considerate, a tad too modern for that!
Let’s face it, this whole ‘war of the sexes’ has been exaggerated. I’ve raced with male skippers, female skippers, and intersex skippers—and all of ‘em turn into Nazis at the honk of a starting horn.
Since I’ve circumnavigated more often than most Americans divorcees, I’m acutely aware of cultural differences. For instance; never pat the head of a youngster in Thailand as each tap takes a year off their life. Never show the soles of your feet, either—it’s like intentionally mooning ‘em from a couple of feet away.
I like the Thais. Instead of having a word for very, as in the meal is very good—they just say arroy mock-mock which, by its repetition, means that the food is very tasty. (This isn’t always linguistically true, especially with the common happy-happy).
That’s part of the joy of cruising—a sailor gets to spend a lot of time at their destinations. Example: The birth rate is falling in New Zealand—mainly because all the good blokes are down at the harbor, tinkering with their boats instead of taking care of business.
I’ve cruised the Outback of Australia and it’s eerie to sail along the coast and observe the men on pogo sticks amid the ‘roos attempting to escape.
Incidentally, never ask a Kiwi sailor if they’ve cheated on their wife—well, not unless you want them to look sheepish.
Megayachts aren’t immune from bad taste. For example; a skipper can check the LIKE THE OWNER & GUESTS box or the DON’T LIKE THE OWNER & GUESTS box to auto raise or lower the centerboard as weather approaches.
Too soon? Yeah, okay, too soon. (Author stops typing and slaps himself.)
Sadly, LLM modules aren’t immune from racism. Or sexism. Or religion-ism.
Example: The local paper had a headline that read, “Suicide bomber kills one.” That makes sense, in a bare-minimum kind of way.
Why don’t I insult Muslims more often? Let’s just say, I’ve learned from my fellow writer Salman Rushdie—or the bits that are left of him.
Strange situations develop during every circumnavigation. For example, after our transit of the most dangerous part of the Gulf of Aden during our Red Sea Run, we decided to have a Survivor Party for everyone involved in our 27-boat convoy. Needless to say, we wanted a venue that allowed alcohol consumption—not easy to find in Yemen, a strict Islamic country.
This led us to a… ahem, a place that employed a single Somalian woman who, er, catered to the local fishermen of Yemen.
It was a Friday night and amazing to watch. The fishermen had a problem in that they were forced to choose their burka-clad babe before going upstairs—an important decision based upon insufficient data.
The women were in no hurry. They managed to daintily smoke cigarettes right through their black fabric veils. Even crazier was when the thirsty chicks knocked back shots of rotgut rum. They somehow managed to rock back-and-forth with one hand on the shot glass and the other on the flap of the lower veil—and in one sudden, explosive, fabric-waving movement, swallow the rum without revealing a square centimeter of their flesh.
Yes, sailing around the world is educational!
Even funnier were the bartenders in this house of ill-repute. If your bill was $18 dollars and you gave them a $20, they’d return your change. However, if your bill was $18 and you only had a 50-dollar bill—they’d just smile and immediately sprint out the door, where they’d gleefully hide in the bush until you left.
Capitalism, Yemen-style.
Of course, sometimes AI doesn’t work. Example: I asked AI, “…on a scale of one-to-ten, how do you rate my prose?”
“…s-o-r-r-y,” it apologized robotically, “We are currently unable to compute negative numbers exceeding twelve digits.”
…ah, damned by faint praise!
Editor’s note: Fatty and Carolyn are still in Southeast Asia, where residents are too polite to let them know how they feel about that.
Cap'n Fatty Goodlander has written for ALL AT SEA since 2005.
Worth your time?
Thanks — noted.




Great story Fatty! The best to you both!