Buying a Sailboat in Hawaii for $8,000 (What Went Wrong)

A true sailing story about Hawaii, bad decisions, and the beginning of a Pacific adventure.

If there is a single moment where everything quietly goes off the rails, it’s usually disguised as a good idea.

In our case, it started on a beach in Maui.

Josh and I met while teaching there, which sounds respectable, but most of our time was spent diving, exploring, and generally behaving like two twenty somethings who had not yet been properly introduced to consequences.

Everything was more fun together. That should have been our first warning.

One evening, we were watching the sun drop into the Pacific, painting the water gold like it was trying to impress us.

Josh said, “I want to get a sailboat and go between the islands.”

I nodded, like a reasonable person.

Then I said, “We should sail to the South Pacific.”

And just like that, we ruined our perfectly normal lives.

How to Save Money in Hawaii (Questionable Methods)

Sailboats cost money. We did not have money.

So we moved into Josh’s Toyota pickup truck.

It was less of a “minimalist lifestyle choice” and more of a “we are now technically homeless but optimistic” situation.

We ate whatever we could find:

Fish we caught
Coconuts we absolutely didn’t own
Mangoes and papayas that fell into our hands through mysterious circumstances
Discount grocery store bread at 5:00 PM

There is something deeply humbling about eating cold garlic bread in a parking lot and thinking, this is part of the plan.

But it worked. We saved enough for a boat.

Unfortunately, the first one didn’t work out.

The Boat That Disappeared

Josh flew to Oahu to buy what he confidently described as “the perfect sailboat.”

A Contessa 26. Strong. Seaworthy. Within budget.

The owner agreed to sell it for $10,000.

Done deal.

Except it wasn’t.

The next morning, on the way to the bank, Josh got a call.

“Ah, today is my lucky day!” the man said. “Someone has offered full price.”

That was it.

No negotiation. No warning. Just… gone.

Which left Josh stranded in Honolulu with one objective:

Find a seaworthy sailboat in Hawaii for under $10,000.

What could possibly go wrong?

Sleeping on Rooftops and Inspecting Floating Nightmares

Hotels were out of the question. Every dollar mattered.

So Josh started sleeping on rooftops.

Yes. Rooftops.

“It’s safer up there,” he told me during our nightly calls.

By day, he searched marinas across Oahu for a used sailboat. By night, he climbed buildings like a very determined, slightly sleep-deprived raccoon.

At one point, someone tried to sell him a boat missing part of the keel.

Josh dove into the harbor to check.

When he came up and pointed it out, the seller just shrugged.

“Well, ain’t that something.”

Yes. Yes, it was something.

It was a very effective way to die at sea.

Finding Tiny Bubbles

And then he found her.

A neglected Pacific Seacraft 25 sitting quietly in the marina.

Not for sale.

But as it turns out, everything is for sale if you ask the right question at the wrong time.

“How much?” the owner asked.

Josh panicked.

“$8,000?”

(He later admitted this number was ludicrously high, but he was feeling desperate).

“I’ll meet you tomorrow,” the man said.

And just like that—we owned a sailboat in Hawaii.

Her name was Tiny Bubbles.

She was… not impressive.

The hull was covered in oysters large enough to qualify as restaurant fare. The cabin smelled like diesel and neglect. And every surface was coated in what looked like wings.

It was in fact termite wings.

We discovered this when Josh casually pushed his thumb through a cabinet.

“Good news,” he said. “The termites are gone.”

I stared at him.

“That’s not how termites work.”

Love, But Make It Questionable

I flew over after finishing summer school.

There’s a specific kind of love required to step onto a boat like Tiny Bubbles and think, yes, this feels like a solid life decision.

That was us.

Deeply in love.

Possibly delusional.

Hard to say.

The First Sailing Disaster

We had one weekend to sail the boat back to Maui.

So naturally, we ignored the weather.

We spent hours scraping oysters off the hull, losing skin to the sharp buggers, until the hull was at least somewhat seaworthy.

Then we left the marina.

At first, it was perfect.

Then we turned on the radio.

“Small craft advisory. High winds and large swell.”

I looked at Josh.

Josh looked at me.

We both pretended this was fine.

By the time we passed Diamond Head, it was no longer fine.

The ocean turned aggressive. The boat slammed and pitched violently.

I lasted longer than expected.

Then I didn’t.

I leaned over the side.

Josh rushed over to hold my hair back.

Unfortunately, I was facing directly into the wind.

What followed was less of a moment and more of a full-body snack redistribution event.

We stood there. Covered. Silent.

“We should turn around,” I said.

“We should definitely turn around,” he agreed.

Back to Harbor (Barely)

We sailed back into Ala Wai Harbor under sail alone, which impressed someone on the dock.

“Hey! You’re doing it party style!”

We were not partying.

We were recovering.

I flew back to Maui the next day.

Josh stayed behind with Tiny Bubbles.

And that’s when things escalated.

Alone, Offshore, and Questioning Everything

The harbor soon to fill with Transpac race boats, and Josh was told to leave immediately.

So he sailed out again.

Alone.

Into worsening conditions.

Somewhere offshore—BANG.

The jib tore loose.

Game over.

He turned toward shore and dropped anchor off Diamond Head in deep water as night fell.

The Coast Guard appeared.

“What’s the name of your vessel?”

“…Tiny Bubbles,” he said.

Pause.

“Do you need assistance?”

“No.”

(This was incorrect.)

They left.

He stayed.

And somehow, unbelievably, the anchor held.

To Be Continued

By the time I returned that Friday, Josh had:

Repaired the sail himself
Hidden from the harbor master for a week
Nearly destroyed the boat
And still believed we should sail to Maui

I walked down the dock, took one look at him, and said nothing.

Then I quietly put a seasickness patch on his neck.

This time, we were going to be ready.

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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