A Serialized Pacific Voyage · Nomadventure.org
Prologue
⚠️ A Word Before We Begin: The Disclaimer Nobody Asked For But Everybody Needs
This is a true story. Or mostly true. True enough that the people involved remember it — though they don't always agree on the details, and memory, it turns out, is not a court-admissible document.
Here is the thing you should know before you read any further: some of the things I did in this story are not legal. Some are not sanctioned by any recognizable authority. Some are not wise, advisable, insurable, or covered by the warranty on your common sense. I slept in places I wasn't supposed to sleep. I ate things I caught in ways that may or may not have required a license. I sailed boats I was not fully qualified to sail. I made decisions that a reasonable person — presented with the same information, the same conditions, and the same complete absence of a backup plan — would not have made.
I am not recommending any of it.
I am not suggesting you try it at home. I am not suggesting you try it away from home. I am particularly not suggesting you try any of it on a boat you bought for eight thousand dollars from a man who seemed relieved to be rid of it.
This blog is a record of what happened, not a how-to guide. The line between "adventure" and "catastrophic lapse in judgment" is, in our experience, mostly a matter of outcome — and we got lucky more times than we deserved. Think of this the way you think of those wildlife documentaries where the filmmaker gets extremely close to something that could kill them: fascinating to watch, inadvisable to replicate, and ultimately a story only because nobody died.
Now. With that out of the way. Let's go back to the beginning.
Before There Was a Boat
The year was 2002, and I had spent the previous twelve months doing something that was either deeply admirable or a mild public health concern, depending on your perspective: living outdoors in the Eastern Sierra Nevada, teaching school by day, and spending every other available hour climbing rocks, mountaineering in deep snow, and conducting what I can only describe as an extended personal audit of my own tolerance for discomfort.
Mammoth Lakes sits at nearly 8,000 feet, which is high enough that the air has a quality to it — thin and crisp. The mountains there are serious mountains. The snow in winter is not the decorative kind. I climbed, I went into those mountains, I bivouacked in places that would have alarmed my mother, and I was, by any objective measure, having the time of my life.
But by the end of that year, something was missing. Specifically: warmth. My hands had been cold and deeply cracked.
The solution arrived in the form of a photograph — someone's snapshot of Maui, all green mountains tumbling down to water so clear it looked photoshopped. A friend mentioned, as we chatted about our deeply cracked hands, that he had once been to Hawaii, and that the beach parks had showers. Public showers. Free. Cold water, presumably, but at least water that was not previously frozen. I did not need further convincing. I had all the information required to make a major life decision.
I drove to the Port of Los Angeles at Terminal Island — a patch of industrial waterfront in San Pedro where, among other things, you can ship your pickup truck to Hawaii for a fee that sounds reasonable until the moment you pay it — loaded my Toyota onto a container ship, and hitchhiked to LAX.
The Mid-Flight Interrogation
On the flight from Los Angeles to Honolulu, I sat next to a woman named Leilani — mid-twenties, part Japanese, part Hawaiian, returning home to Oʻahu after a trip to the mainland. She was warm and easy to talk to, and within approximately four minutes of reaching cruising altitude, she had identified that I had no plan whatsoever for my time in Hawaii.
She did not reach this conclusion through intuition. She reached it through a methodical line of questioning that any experienced interrogator would have admired.
"Where are you staying in Maui?"
"I haven't quite sorted that out yet."
"How long are you planning to be there?"
"I'm leaving it open."
"Do you know anyone on the island?"
"Not exactly, no."
"What are you going to do for work?"
I told her I was a teacher. She nodded and added this to her growing dossier.
"What are you going to do for money, Hawaii is super expensive.”
I told her I was optimistic about this question. She wrote something in the margins of her mental notepad.
By the time Big Island appeared below us — a dark volcanic mass rising out of the Pacific with the blunt authority of something that does not need your approval — she had formed her conclusions. She turned to me with the measured expression of someone who has done this assessment many times before and has learned to deliver the results without flinching.
"Josh," she said, "I meet a lot of people relocating to Hawaii. Usually it's a terrible match." She paused. "But your attitude is gold. You're a rare one that's going to fit right in."
I want to be honest: I don't know exactly what she saw. I was a man with no accommodation, no contacts, no plan, and a truck that would arrive by container ship sometime in the next week or two. Whatever she detected in my disposition that qualified as "gold," I am grateful she found it, because it was the only thing I had going for me at that moment.
The Costco Parking Lot Option
My truck had not arrived yet. This was a logistical inconvenience I had anticipated in the sense that I knew it would happen, and had not prepared for in the sense that I had made no arrangements for the intervening period.
The beach parks of Maui, it turned out, were an excellent solution. During the days I swam in water that was, as advertised, completely unreasonable in its beauty. At night I strung my hammock high in the trees, which is both comfortable and invisible, which are two qualities that matter when you are sleeping somewhere you have not been formally invited to sleep.
When a rainstorm came through one evening — the kind of warm tropical downpour that is pleasant if you are inside and clarifying if you are not — I moved operations to a parking lot behind a Costco, where a row of semi-trailers sat overnight. I strung the hammock between the frame rails underneath one of them, high and dry, six inches above the pavement, listening to the rain hammer the roof of a forty-foot container truck while I contemplated my life choices. The arrangement had one non-negotiable rule: break camp before the driver came back in the morning. I held to this without exception, because there are certain conversations and/or hammock speeds you simply do not want to experience.
Then my small daypack got stolen.
I was in the water — properly in it, the kind of swimming where you surface fifty yards from where you went under and lose all awareness of the material world — and when I came back to shore, the pack was gone. It contained my tax documents, and various other pieces of paper that the civilized world uses to confirm you exist. Someone had taken all of it.
They also, I noted later, had not done my taxes.
I stood on the beach, dripping, and took inventory of what remained: my larger pack, my fins, my dive mask, some clothes, and a wallet that contained enough money to get started. I was lighter, more mobile, and — once the initial irritation passed, which took approximately one afternoon — genuinely better off. The stolen documents had, in retrospect, been weight. Hawaii, I was learning, had its own way of editing your life down to what you actually needed.
The Truck Arrives. West Maui Opens Its Arms.
The Toyota came off the container ship and I pointed it west toward Lāhainā, chasing the dry side of the island where the sun hits the water without apology and the trade winds smell of salt and plumeria and the particular freedom of having nowhere to be. I parked at a beach park, hung my hammock from a kiawe tree, and established a morning routine that I am not sure I have improved upon since.
Every morning I entered the water with fins, mask, and pole spear. Whatever I speared for breakfast was cooked on a two-burner propane camp stove on my tailgate. I was eating octopus, squid, surgeonfish, and goatfish. I was a waiter at the Westin. I also lived in a truck. These facts coexisted without apparent conflict.
The regulars at the beach park became my community. Among them: a ninety-year-old Japanese-American man named Peanut, who walked the park every single morning at the same hour with the unhurried authority of someone who has outlasted all urgency. Peanut had white hair, a slow careful gait, and the conversational precision of a man who had decided long ago to say only what was worth saying. We talked every morning — about the water, the fishing, the weather, the way the mountains looked from the beach. He had, I came to understand, seen everything there was to see about Maui, and he shared it in pieces.
One morning he stopped at my tailgate and looked at me for a long moment without speaking.
"Your face," he said finally, "looks different."
"Good different or bad different?"
"Puffy," he said. "Like a fish."
He was not wrong. That morning I had speared a filefish off the reef — a striking creature, gray-green with a rough leathery skin and a single locking spine on its back, common on Hawaiian reefs and, in my experience up to that point, completely edible. I had brought it back, filleted it on my tailgate, and cooked it up. It had tasted extraordinary. Like scallops. Better than scallops. I had eaten the entire thing with considerable satisfaction.
By 8 o'clock that morning my hands had begun to swell. By nine my face had followed. I was experiencing what is known clinically as scombroid fish poisoning — a histamine reaction caused by improperly chilled fish in which the body essentially stages a protest, inflaming everything it can reach as a way of expressing its displeasure. It is not dangerous in the way that, say, falling off a cliff is dangerous, but it is very convincing in the moment.
I found a Benadryl in the top of my large pack, took it, and lay in my hammock while the antihistamine negotiated a ceasefire with my immune system.
The Indefatigable
My introduction to sailing arrived, as most things arrive in a good story, through an open hatch and an upward glance.
I had developed a habit of diving through the Mālā Wharf mooring field — a shallow, clear-water anchorage just north of Lāhainā where cruising boats sat at moorings and the fish gathered around the pilings in the dappled light. It was excellent for spearfishing, and it brought me into contact with every boat in the field in an unusual way: I saw them from below first, their hulls dark against the refracted surface light, their keels hanging down in the blue.
One morning I surfaced alongside a boat I hadn't seen before — a steel-hulled cutter with the heavy, purposeful lines of something that had been built rather than purchased. From the water, looking up, I squinted past my mask at the figure on deck.
"Nice boat," I called up.
The man looked down. He had the lean, weathered look of someone who had spent serious time at sea — not the decorative kind of weathered you get from a charter vacation, but the structural kind, where the sun and wind have worked their way into the architecture of the face. His name was Finn, and he had built this boat himself, in his yard, over the better part of a year — which is magnificently fast for this sort of endeavor. He and his partner Mary had sailed it down from Alaska and were on their way to New Zealand. The boat was called Indefatigable.
This is, objectively, an extraordinary name for a boat. The original HMS Indefatigable was an 18th-century Royal Navy frigate whose name meant, essentially, "incapable of being tired out." Finn's version was a steel cutter about thirty-six feet long, cream-hulled, and — I learned when they invited me aboard — spotlessly organized in the way that boats become when two capable people have lived aboard them for a long time and have resolved all their disagreements about where things go.
Mary was Finn's equal in every department — same age, same competence, same calm efficiency at sea that suggested sailing together had become a single coordinated act rather than two people managing separate tasks. They moved around the boat the way longtime dancers move: no wasted motion, no need for narration.
They took me sailing in the open water off Mālā Wharf, and they were generous with their instruction — which primarily took the form of throwing a life jacket over the side and requiring me to help retrieve it. Finn steered. Mary pointed to where the jacket was floating and called out the angles.
"There — two o'clock. Come up a little. Now bear off."
And then: "Your turn."
They handed me the helm of a boat I had never touched, on open water, with a tacking drill already in progress, which is the nautical equivalent of handing someone car keys while the vehicle is already moving. I gripped the wheel with both hands and a specific kind of terror that I have since come to recognize as the leading edge of competence — the moment just before you know you can do something, when your body has not yet caught up with the information your mind is processing.
I did not break the boat.
I did not break it, and when we came back into the anchorage and Finn fired up the engine to prepare for the mooring, the change from sailing motion to engine motion hit me below the waterline, so to speak. The world rearranged itself. I handed back the helm, thanked them both, and went over the side into the clear water with the practiced casualness of someone who had absolutely planned to do that and was not at all re-establishing contact with a stable reality.
The cool water was very clarifying.
Before they left — and they did leave, sailing south toward the Society Islands with the calm purpose of people who always knew they were going — Finn stood in the cockpit and pointed across the mooring field to a particular boat. A small, yawl. Sitting very still. The kind of still that suggests a long residency.
"That one," he said, "would make a nice cruising boat. She's probably not going anywhere. Might be worth a conversation."
He said it the way people say things when they know more than they're offering — like he'd noticed the boat before, maybe knew something about its history. I filed it away.
Indefatigable sailed out of the mooring field the next morning, and I watched her go from the beach — the steel hull catching the early light, the sails going up one by one as she cleared the field and found the wind. I had two hours of sailing experience and the dawning suspicion that my life had just taken a turn I hadn't planned for.
The Yawl
I tried the same approach with the boat Finn had pointed out: swam to it from below, surfaced alongside, looked up.
A face appeared at the rail. Early seventies. White stubble, squinting eyes, the particular expression of a man who has been interrupted at something undemanding and is deciding whether to be annoyed about it.
"Nice boat," I said.
His name was Tim — a retired Marine, a mainlander who had found his way to Maui and stayed, the way people do when the mainland loses its argument. He was also, I would learn, an old-time longboarder — the kind who had surfed before surfing had a demographic, before it had a magazine, when the boards were made of wood and the whole enterprise was still something you did rather than something you performed. He lived aboard the boat with modest means and the VA hospital nearby and what appeared to be a deep personal contentment that had nothing to do with any of the things the rest of the world was busy acquiring.
The boat smelled of diesel. Diesel odors had permeated everything — the wood and the upholstery, and anything that stayed below deck. Every surface had something on it. Charts, tools, books, spare parts, fishing gear, objects whose purpose I could not immediately determine and did not ask about. It was a boat that had accumulated a life.
Tim had no intention of going anywhere. He told me this without apology. The boat was his home, the mooring was his address, and the idea of casting off and sailing somewhere — while theoretically available to him — was not something he felt the need to act on.
"But if you ever want to take her out," he said, "I'm game."
I came back.
The Second Sail, or: A Complete Inventory of Things That Went Wrong
We prepared the boat the way you prepare a boat that hasn't been sailed in years: slowly, with frequent pauses to assess whether a given piece of equipment was going to cooperate or simply hold its position on the spectrum between "functional" and "not our problem anymore." The sails went up with some persuasion. The lines ran. The engine, which Tim started with the confidence of someone performing a ritual he believed in despite mixed results, produced a sound like a large man clearing his throat and then did, in fact, run.
We let go of the mooring.
The engine stopped.
Not gradually. Not as a warning. It simply stopped, with the finality of something that had been looking for an exit and had found one. We were now adrift in a mooring field full of other people's boats, powered by sails, steered by a man with approximately two hours of sailing experience.
We got out. I don't know precisely how — it involved some sail trim I executed on instinct and some luck I am happy to claim credit for in retrospect — but we cleared the mooring field and pointed south along the West Maui coast, and Tim went below with his book.
I want to dwell on this for a moment. We had just escaped an engineless drifting situation in a crowded anchorage, and Tim went below with his book. He had, I would come to understand, simply recalibrated his trust downward to meet the available evidence and arrived at an equanimity about outcomes that I found both inspiring and faintly alarming.
I sailed south. The water was clear and calm close in, and I was watching the coast go by with the particular pleasure of someone doing something new and finding, to their surprise, that it's working.
Then I looked over the rail.
The bottom was coming up.
In the clear Hawaiian water you can read depth the way you read a map: deep water is dark blue, transitional water is lighter, shallow water over sand is pale green, and water over coral is a mosaic of colors that means something important about where you absolutely do not want to put a keel. We had drifted close inshore — how close, I could not say precisely — and now the bottom was rising toward us through crystal water with the patient inevitability of something that was not going to move on our behalf.
The boat drew nearly five feet. The water beneath us, at my best estimate, was about five feet. The coral heads around us were the kind that do not yield.
Tim was below with his book.
Tim had already had surgery for a heart attack. I did a fast calculation and determined that informing him of our precise situation was not going to improve it. I pulled the helm hard over, pointed the bow toward deeper water, eased the mainsail as far as it would go, and said something private and urgent to whatever forces govern the outcomes of avoidable disasters.
The boat turned. The depth increased. The coral receded below us in the water and the blue came back and my heart, which had relocated to the general vicinity of my throat, returned slowly to its correct address.
I pointed the bow toward Lānaʻi — that quiet island on the horizon, eight miles across the Auʻau Channel, where the water was deep and honest and there was nothing to run into — and I practiced tacking.
A Close Encounter
On one tack, I heard it: a tremendous tearing sound, sudden and sharp, like canvas splitting under load. I looked up at the mainsail. Nothing. The sail was full and drawing, the leech clean, no obvious catastrophe visible from where I stood.
Then I heard it again.
But from the wrong direction.
I turned.
Alongside the boat — close enough that I could see the barnacles on its rostrum, close enough that its eye was visible above the waterline, an eye the size of a dinner plate tracking me with what I choose to interpret as mild curiosity — was a humpback whale. A large one. The kind of large that recalibrates your sense of scale, where a boat that had previously seemed like a meaningful object in the water is suddenly revealed to be a very small thing indeed.
It exhaled. That was the sound — the explosive breath of a forty-ton animal releasing air through a blowhole, a sound like a sail tearing, like the world briefly sighing. It was close enough that the mist of the blow settled on my face.
I did not move. I am not certain I breathed.
The whale sounded — that slow, enormous arc of the back, the tail rising — and was gone, back into the blue with a silence that seemed impossible for something that size. I stood at the helm and stared at the water where it had been.
Every year between November and May, roughly ten thousand North Pacific humpback whales make the 3,000-mile journey from their feeding grounds in Alaska to the warm, shallow waters around Maui to breed and calve. The ʻAuʻau Channel — the strip of water between Maui and Lānaʻi that I was currently sailing — is their preferred nursery. In 2002 the population was still recovering from the whaling era; today there are estimates of 10,000 in the North Pacific alone, and Maui's waters hold the highest concentration on earth. I had, without intending to, sailed directly into one of the great wildlife spectacles on the planet. The whale had appeared alongside me not because it was confused or distressed but simply because it lived there and I happened to be passing through.
I turned the boat back toward Maui.
Sailboats Don’t Have Brakes
The approach to the mooring field under sail — no engine, no margin for error — required the kind of focused attention that makes everything else temporarily stop existing. Tim came up from below and I passed him the tiller. Our plan, such as it was, was to come in under full sail, slow the boat by heading up into the wind, and have me lean over the bow and grab the mooring pendant as we passed over it. The pendant is a short line hanging in the water from the mooring buoy, and grabbing it requires you to be at the right height, moving at the right speed, at precisely the right moment.
We came in too fast.
I draped myself over the bow pulpit, one leg hooked around the forestay for what I will generously call "security," reaching for the pendant as the boat bore down on the buoy. I got it. Both hands around the line, and then the full momentum of a several-ton boat — still moving, entirely uninterested in my preference for stopping — transferred directly into my arms.
I let go. There was no alternative. The choice was between letting go and going over the bow, and I chose letting go with a speed that required no deliberation.
Tim called out, “Why’d you drop it?”
“Dude, do I look like Hercules to you?” I retorted. “Tack it over and we’ll try again.”
I scrambled back to take in the headsail sheet on the other side, as we sailed back around in a large arc, and eased out the mainsail.
This time he headed up into the wind earlier, letting the mainsail luff and the boat lose way, bleeding speed until we came over the pendant barely moving. I grabbed it, and had it over the cleat and made fast before the momentum could build again.
We were on the mooring.
Tim went below.
I sat on the bow for a long time, legs dangling over the water, looking at the anchorage and the mountains behind it. My arms felt like they'd been through something. My heart was doing the slow-motion replay that follows a near-miss.
I had now been sailing twice.
I had nearly grounded a borrowed boat, and someone’s home, on a coral reef, been buzzed by a humpback whale, and nearly gone over the bow of a vessel I had no business crewing. I had learned more in those two afternoons than I could have absorbed from any book.
Next: Chapter 1 — Josh is eating fish in a school hallway when someone interesting walks by.
© 2026 Heidi & Josh. All Rights Reserved.
This story is based on real events. Some names, dialogue, and identifying details have been changed or recreated for narrative purposes.
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