Chapter 5: The Abyss Looked Back, and Then We Got Seasick
There is a specific kind of misery that sailing people rarely admit to in polite company, which is that going to windward at night in a seaway is about as pleasant as being repeatedly hit with a cold, wet mattress. You know it's coming. You brace for it. It hits you anyway.
We left Oʻahu in the early evening, holding a compass bearing designed to hit the southern tip of Lānaʻi — a landmass roughly twenty-five miles of open Pacific to the southeast. The plan was straightforward: sail through the night, round Lānaʻi's southern shore in the morning, and work our way up into the calm waters off West Maui, where we would anchor and begin the serious business of preparing Tiny Bubbles for the South Pacific.
The plan, as plans often do, remained straightforward only until we left the harbor.
The Weather Helm
If you have never sailed to windward in strong trade winds on a boat the size of a generous automobile, let me describe the experience. The bow rises on an incoming swell, hangs briefly at the apex, and then drives down the back side with a sound like a filing cabinet falling down a staircase. This repeats continuously. The sails are sheeted hard. The tiller — which on Tiny Bubbles was a direct mechanical extension of the rudder, with no power steering and no mercy — pulls constantly toward the wind, a phenomenon sailors call weather helm.
Weather helm is normal. A well-tuned sailboat will always want to round up into the wind, a built-in safety mechanism that traces back centuries. What this means in practice is that you spend an entire night fighting a piece of wood for control of your direction, and the piece of wood, unlike your burning biceps, never gets tired.
We took turns at the tiller in one-hour watches, which felt like a reasonable arrangement until about midnight, when one hour began to feel less like a watch and more like a sentence.
Heidi came off her first watch with the expression of someone who has just completed a very intense argument.
I took the helm. She was not wrong. The tiller leaned into my hand like an insistent dog that has spotted something across the street. I leaned back. The bow smashed through a swell and a curtain of cold salt spray came over the bow and drenched us both.
The channels between the Hawaiian Islands have a well-earned reputation. The trade winds — driven by a semi-permanent high-pressure system sitting north of the archipelago — blow steadily from the northeast across open ocean, accelerating as they funnel between the islands' mountainous bulk. Maui's Haleakalā volcano rises over ten thousand feet, and Lānaʻi sits in its rain shadow. When those winds hit the gaps between islands, they compress and speed up, in the same way water moves faster through a narrowed hose. Sailors who have been through the channels once tend to plan their subsequent passages very carefully around them. Sailors who haven't yet been through tend to read about this afterward, nodding slowly.
We were in the second group.
Daybreak
At some point in the small hours, the character of the motion changed. I had been on watch for ninety minutes, crouched against the coaming, tiller gripped in both hands, watching the compass card swing and correcting, swing and correct — when I realized the swings were smaller. The bow was rising more gently. The spray had stopped.
I looked up. The eastern sky had gone from black to the particular purple-gray that precedes everything, and ahead of us — perhaps four miles — a dark mass of land sat against the lightening horizon. Lānaʻi's southern cliffs. We had held the bearing through the night, and the island had blocked the wind and swell exactly as planned.
I had been sailing for less than a year. I had never navigated by compass through an open-ocean night crossing. The fact that we were precisely where we intended to be felt, in that moment, enormously significant — the kind of thing you want to record, to tell someone, to commemorate in some way. But Heidi was asleep below, and the moment slipped past in the quiet, the way good moments often do when there's no one to witness them.
I let the mainsheet ease and Tiny Bubbles settled into a gentle reach, moving through the flat water in Lānaʻi's lee.
Then we stopped.
The Cork
No wind. Completely, perfectly, aggressively no wind.
The trade winds that had been battering us all night ended abruptly in the island's shadow, as though someone had closed a door. Tiny Bubbles slowed, wallowed, and then simply sat there, rolling side to side in the remnant swell with a rhythmic, inelegant motion — like a bathtub toy left behind by a wave. The boom swung back and forth. Everything below that was not secured began announcing itself.
We had no engine. This was not a new development — we had known for a week that the engine was a decorative item requiring future attention — but the knowledge takes on a different quality when you are sitting motionless in a channel that needs to be crossed.
Heidi came up from below and assessed the situation with the brisk practicality that I was beginning to understand was simply how she processed adversity.
"So we're a cork," she said.
"We're a cork."
"How long?"
"Until the islands heat up and make their own wind." I looked at the sun, just clearing Lānaʻi's ridge. "Few hours, maybe."
She handed me water bottle. "Good. I've been wanting to swim."
A Brief History of Bad Ideas
The water around the Hawaiian Islands is, in the right light, the color of a swimming pool in a magazine. Not a real swimming pool — a magazine swimming pool, the kind that exists only in advertisements for resorts you can't afford. Gin clear. You can see the bottom at thirty, forty feet. You can see your own shadow on the sand far below.
I told Heidi about the stories. Every sailor who has spent time on the water has heard some version of them: the becalmed vessel, the heat, the irresistible blue water. The crewmembers who go over the side for a swim. The swimmers, treading water in the deep ocean realize they don’t have a plan for getting back onboard. They try desperately to climb the sides. The desperate attempts to find a handhold that doesn’t exist. The exhaustion that sets in, and finally the discovery of the abandoned vessel, days later. The fingernail scratches along the hull.
I had intended this as a cautionary note.
"So, we’ll go one at a time,” Heidi said, as she grabbed her mask and disappeared in a splash.
This was, I had to admit, a reasonable solution. Besides, we had climbed aboard the tiny boat easily after cleaning oysters off the week before.
Heidi grabbed the side rail, pulled herself up like an action hero, and rolled under the lifelines.
My turn. I donned my mask and took the plunge. I am floating in the Pacific Ocean in approximately one thousand feet of water, completely detached from my twenty-five-foot sailboat. It is, without question, the most beautiful thing. I want to record the color of this water but there's no word for it. The closest I can get is: imagine you could see all the way to the bottom of space.
What I did not anticipate — and what I should have, if I had read more carefully about scopolamine transdermal patches — was what happens to seasickness medication when it gets wet.
Scopolamine is delivered through a small adhesive patch worn behind the ear. It is genuinely effective at suppressing the nausea and disorientation that accompanies a boat moving in several directions at once. We had been wearing patches since Honolulu. The patches, it turns out, require dry skin to function correctly.
Immersion in the Pacific Ocean is not consistent with dry skin.
Within minutes of climbing back aboard, we had both identified that something had changed in our relationship with the horizon, and the boat’s motion. The ocean, it turns out, has a deeply personal vendetta against your digestive system, and it will express this grievance loudly and repeatedly until you are left draped over the railing like a sad piece of forgotten laundry, questioning every decision that led you to this moment.
Heidi pulled out a second round of patches.
Thermal Winds
Here is something interesting about Hawaiian islands that has nothing to do with nausea, which is a welcome change of subject.
On calm days, when the trade winds ease or disappear entirely, the islands generate their own local wind systems through differential heating. The land heats up faster than the surrounding ocean. Hot air rises from the slopes and valleys. Cooler sea air rushes in to fill the low pressure left behind, creating a predictable onshore breeze that builds through the morning and dies at sunset. Sailors who know about this — who know to wait for the island's thermal cycle — can work their way around a calm coastline by reading these local winds, island by island, headland by headland, the way a climber reads rock.
We knew about this, in theory. We had read about it. What we had not fully internalized was that the process takes a while, and that "a while" when you are seasick on a rolling boat in direct tropical sun is a unit of time that expands in ways that would interest a physicist.
But the winds came. First a breath off Lānaʻi's southern cliffs, barely enough to fill the main. Then something more consistent as we worked around toward the island's western shore. We ghosted north in light air, coaxing Tiny Bubbles through each lull, watching the water for the signs a puff was coming, adjusting sails to catch each one. By late morning we had rounded the island's southern point and picked up a steadier breeze out of the south-southwest that carried us up into the ʻAuʻau Channel and toward the green mountains of West Maui.
We started to feel human again. Marginally.
"Never doing that again," I said, touching the patch behind my ear.
"The swim or the sailing?"
"The swim. The sailing is non-negotiable."
Heidi smiled. "I'm absolutely doing it again."
Māla Wharf
Māla Wharf sits about a mile north of Lahaina town on Maui's western coast, and it has one of the more entertaining failure histories in Hawaiian infrastructure.
It was built in 1922 by the U.S. Army Corps of Engineers, intended to serve as a loading dock for the Pioneer Mill sugar plantation upslope and the Baldwin Packers pineapple cannery nearby. Local Hawaiians, who had been reading these tides and currents their entire lives, strongly recommended against building it in that location. The Army Corps of Engineers, in the tradition of large institutions that have been given a budget and a deadline, built it anyway.
The first cargo ship to use it crashed into it.
This is not a metaphor, though it could be. It is simply what happened. The currents were too strong and unpredictable for large vessels to navigate safely, exactly as the locals had said they would be. The wharf was repurposed almost immediately for smaller inter-island ferries and passenger boats, then for fishing and recreation, then for nothing official at all after the state closed it around 1959. Hurricane Iniki finished the job in 1992, collapsing the outer sections into the sea, where they became an extremely popular dive site. Because nature has a sense of irony.
What remained of Māla by the time we arrived was a concrete pier, a small boat ramp, some offshore moorings, and — sitting on the sandy bottom in about twenty feet of water — a large steel cylinder.
I had spotted it on a previous dive. It was massive. Industrial. The diameter of a small car, flared at both ends, steel thick enough to suggest it had been manufactured to move something very heavy or hold something very large under very serious pressure. It had been sitting there for a very long time. It was going nowhere.
I had looked at it and thought: if I can get a chain around that thing, we'll never drag.
The Mooring
We ghosted into the anchorage in light afternoon air, sails barely drawing, and let the hook go in the sand nearby. The anchor bit. Tiny Bubbles swung around and settled, and for a moment we just sat there, feeling the strange stillness of a boat that has stopped moving after twenty hours of not stopping.
"We made it," Heidi said.
"We made it," I agreed.
Neither of us moved for several minutes.
Then I explained the plan. The steel cylinder on the bottom. The chain. The shackle and seizing wire. If we could pass a chain around it and lock it off properly, we'd have what sailors call a bombproof mooring — an anchor point so solid that we could leave the boat unattended without worrying, and sleep aboard through the infamous Kona storms.
Heidi looked at the water. She looked at me. She looked back at the water.
"How deep?"
"Twenty feet, give or take."
"How many dives?"
"Probably a lot."
She pulled her hair back. "Okay. You go first and show me what we're doing, and then we'll take turns."
This is one of the things about Heidi that I had been noticing since the beginning: she approaches the unknown not with enthusiasm exactly, but with a kind of cheerful willingness that bypasses the hesitation most people feel. She doesn't require assurance that something is going to go well. She just needs to know what it is and where to start.
I went first. Twenty feet is not a great depth in absolute terms — competitive free divers go to two hundred. But twenty feet is enough that by the time you reach the bottom, you have used a meaningful fraction of the breath you took at the surface, and you are aware, in a very physical way, that your air supply is finite and local and entirely non-negotiable.
As I dove to the bottom, equalizing my ears as I went, I reached the cylinder in the sand and started digging at the sand beneath one end with both hands. The sand moved. I got a handspan clearance under the flared lip, decided it wasn't enough, and came up.
Heidi was waiting at the surface with the expression of someone who has been timing things.
"I made some progress," I said.
"My turn," she said, and went.
We traded off like this for the better part of an hour — one person on the surface, one person on the bottom. Twenty feet doesn't sound like much until you've done it thirty times.
Getting the shackle locked off was its own project. The pin had to be threaded through the chain links and then the seizing wire — a length of thin stainless wire — had to be threaded through the hole in the pin's end and twisted tightly enough to prevent the pin from backing out under load. This sounds simple. Doing it at twenty feet, with burning lungs, tired fingers, and sand in everything, is an entirely different matter.
I came up from the final dive, handed Heidi the end of the mooring line, and floated on my back for a moment, staring up at the sky.
"Done?" she asked.
"Done."
She pulled it tight, tied off the line to our bow cleat, and retrieved our now redundant anchor.
The boat pulled against the mooring. The mooring held. The cylinder on the bottom wasn't going anywhere — it had been sitting there since before either of us was born, and it was going to sit there through whatever Maui's weather wanted to throw at it. We were attached to something solid, and solid was exactly what we needed.
We collapsed into the cockpit, side by side, shoulder to shoulder, too tired for complete sentences.
The sun was getting low over the water. The West Maui Mountains behind Lāhainā caught the last of the light and went gold. A humpback whale — they winter in these waters by the thousands, arriving from Alaska each November to breed in the warm shallows — surfaced out in the channel, exhaled a plume of mist, and slid back under without ceremony.
"Did you see that?" Heidi said.
"Yeah."
A Note on What Comes Next
We had a mooring. We had arrived. We had a boat that needed, by any honest assessment, a substantial amount of work before it was going to be ready to put to sea.
Sitting in the cockpit that evening, looking at the list I had started in the back of a notebook — rigging, engine, sails, electronics, water system, termites — I felt the particular combination of excitement and mild existential dread that accompanies the moment you realize a plan you have been making in the abstract is now simply the thing you are doing.
Heidi read over my shoulder.
"This is a lot," she said.
"Yes."
"Good thing we have time."
Tiny Bubbles sat in the dark off Māla Wharf, tugging gently at her chain, attached to a piece of industrial history.
We were, by any reasonable measure, exactly where we needed to be.
© 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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