This is a true story.
We sailors are a peculiar breed. And some of us suffer from a form of seasickness that has nothing to do with rough weather and everything to do with misguided judgment.
We whinge endlessly about maintenance, rising costs, unreliable engines, leaking ports, and the insanity of crawling into spaces designed for Gumby.
But…show us a neglected 45-year-old sailboat with an old diesel, antique wiring, and a suspiciously low asking price, and suddenly we’re in love.
It’s a sickness. And I fear there is no cure.
Pride and Poor Judgment
Here’s the thing about sailors: we’re not stupid people.
Most of us understand basic economics. We know that spending $40,000 restoring a boat worth $25,000 is not, strictly speaking, a sound financial strategy. In fact, we know it’s a horrible one.
We also know that “just needs a little TLC” can mean anything from a weekend with a bottle of teak oil to a complete structural and mechanical resurrection. A total refit.
And yet, put us aboard a tired, sad old sailboat with good bones and something happens to our brains.
We stop seeing problems and start seeing possibilities.
That leaky portlight? Easy fix.
That ancient electrical panel? Probably time for an upgrade anyway.
The engine that hasn’t run in three years? Well, Perkins built those things to last forever, didn’t they?
And that suspicious-looking stain beneath the chainplate? That? Probably nothing.
We’re dreamers masquerading as practical, sensible people.
Which brings me to my fellow sufferers: Green Mountain Josh, Canadian Ken, Save The Day Jay, and, of course, Captain Kew.
Between us, we possess a considerable amount of sailing experience, a reasonable understanding of boat maintenance, and apparently not one functioning ounce of financial restraint.
The Curious Incident of the Hallberg in the Night-Time
Back during the summer, Canadian Ken and I profiled a beautiful old Hallberg Mistral 33.
She was one of those boats that reminds you why people fall in love with classic sailboats. As Ken put it, more or less, “If you conjure up what a sailboat looks like in your mind, this would be it.”
Beautiful lines, lovely woodwork, and character that’s increasingly hard to find in modern production boats.
She also needed love. Quite a bit of it - but mostly woodwork. Something, say, a carpenter could handle…Did I mention Josh is a carpenter?
Ken and I poked around, filmed our episode, discussed the good and the not-so-good, and went on our merry way.
End of story.
Or so I thought.
A few nights later, Green Mountain Josh was up in Vermont, watching our video with a cold beer in hand.
Then came the call.
“Hey, Tris. What else can you tell me about that Hallberg?”
I’ve known Josh long enough to recognize the symptoms. An innocent question about a boat is rarely innocent.
He was coming to town and thought he’d have another look.
Just a look.
Famous last words.
Well, poke around he did.
Then he called the owner.
Then he called me.
“Wouldn’t take much to fix her up. I’ve got the carpentry skills. And she’s only six grand. Short money, if you think about it…”
Short money.
Two of the most dangerous words in the English language when spoken by a sailor contemplating a project boat.
Six thousand dollars! For a Hallberg! A proper little Swedish cruising yacht!
Never mind the repairs, the time, or the fact that neither of us needed another boat.
At that price, how could we possibly go wrong? I suspect bankruptcy attorneys have built entire careers around that question. And just like that, the wheels were turning.
We could fix her up. Bring back the brightwork. Repair the rotted compression post. Get her sailing again. Maybe document the restoration. Maybe find her a new owner when we were finished. Maybe throw her into our charter fleet. Or maybe make her our weekender boat - and wouldn’t we be a sight to see pulling into a quiet anchorage on this beauty?
The possibilities were endless.
Fortunately, someone else bought her before we could get ourselves into trouble.
Literally saved by a complete stranger.
Whoever you are, thank you.
I think.

The Brewer Ultimatum
You’d imagine that experience might have taught us something.
It did not.
Recently, Josh and I went to film a 1983 Brewer 12.8 center-cockpit cutter.
Forty-two feet of substantial bluewater cruising sailboat, designed by the late Ted Brewer, a man for whom we have a particular affection. After all, he designed our Morgan 382. This was the kind of boat that conjures up distant anchorages, warm trade winds, and the possibility of disappearing for six months with a decent chartplotter and a well-stocked liquor cabinet.
And this particular boat has a beautiful liquor cabinet.
We were doomed.
Now, to be clear, none of us needs another boat.
In fact, just a few years ago, Ken and I filmed a pretty Morgan 384 and talked about what a wonderful boat she'd be to own. You know, just so we could "experience the differences between the 382 and 384."
So, naturally, two years and a simple twist of fate later, we bought her. That one’s on Ken.
He looks innocent enough…
So much for objectivity.
We already have boats. We have projects. We have plenty of legitimate reasons to spend our weekends covered in grease, fiberglass dust, and bottom paint.
But we were curious.
And curiosity, combined with an aging cruising sailboat, is a dangerous thing.
The Brewer needed love.
There were repairs to make, systems to evaluate, and enough deferred maintenance to give any reasonable person pause or maybe angina.
We noticed all of it.
We discussed the problems, considered the fixes, and contemplated the costs.
The asking price was $25,000.
As Josh quipped, “The first $25K is easy. It’s the second $25K that’ll get ya.”
For the record, even the first $25K wouldn’t be easy!
And then something entirely predictable happened.
We started figuring out how we’d do it.
Not whether we should.
How.
That’s an important distinction.
Before long, we’d mentally repaired half the boat, drawn up a list of improvements, and imagined what she’d look like after an off-season of attention.
And then came the rationalizations.
What if we chartered her? We could charge a pretty penny for a 42-foot cruising boat with a private aft cabin and en suite head. After all, chartering helped pay for our second Morgan. Why couldn’t we do it again?
Suddenly, we weren’t just saving an old sailboat. We were making a brilliant business decision…
Or so we told ourselves.
Two reasonably intelligent men had become two boys in a candy store, with just enough money in their pockets to get into serious trouble.
Saved by the Mooring
Eventually, Josh and I came to our senses.
Mostly. Actually, that’s a lie.
It took just about every ounce of self-control we possessed not to buy her.
Not because we needed her. Not because we had some brilliant business plan. Although, come to think of it, we kind of did.
But because we really, really liked her.
We liked what she was, what she could become, and the idea of being the guys who brought her back.
Fortunately, reality intervened.
How would we tell Canadian Ken? He'd probably flee to Canada and have the border closed behind him.
Then there was the small matter of where we’d put her.
We don’t have another mooring.
Which may be the only thing standing between us and a truly spectacular lapse in judgment.
Of course, moorings can be found.
And therein lies the danger.
Then there was fate: Once again, someone else came to our rescue. The owner informed us she’d received an offer she intended to accept.
Apparently, we’re not the only ones with questionable judgment and excellent taste.
One Flew Over the Boatyard
And then there’s Save The Day Jay, the newest member of our delusional little tribe.
While poking around a local boatyard, Jay stumbled upon a Cal 39 MKII that had been sitting in a barn for a decade. Remarkably, she was nearly perfect. Just needed a good cleaning and a few updates. At least on the surface.
“Charter boat for the fleet?” he asked.
“Let’s get Josh to come look at her,” I replied.
See what I mean? Neither of us suggested leaving well enough alone. And that beauty is still sitting in that barn. I can still hear her siren’s song. And Jay? He’s got the sickness for sure.
The Devil Wears Red & Green Suspenders
And then there’s Captain Kew. Some of you might remember him as Captain Q. Same sound, same man, different spelling.
If ever there was a devil sitting on one’s shoulder, whispering sweet nothings about old sailboats, it’s The Captain. Hardly a day goes by without another tempting listing appearing in my inbox.
Most recently this was a Morgan 383 located within striking distance from my home.
“You know, you could round out the fleet. A 382, a 383, AND a 384. Same boats, more or less. Same systems...ideal for your charter fleet.”
The man makes a compelling argument.
Which is precisely why he’s so dangerous.

We’ve met people with three boats who are contemplating a fourth. How bad can it be?
We’ve met people who’ve spent more money restoring a boat than they could ever hope to recover.
People who insist they’re downsizing, only to buy something six feet longer.
And people who haven’t sailed in years but still can’t bring themselves to sell the boat sitting in their backyard.
Are we irrational?
Absolutely.
Hopeless romantics?
Probably.
Here’s the thing: There’s something wonderful about a community of people who can look at a nearly exhausted, 43-year-old sailboat and see not just a collection of problems, but a whole world of possibilities.
Maybe that’s what keeps these old boats alive.
Maybe that’s what keeps us going.
Or maybe we’re all just a little nuts.
Either way, I suspect Josh, Ken, Jay, The Captain, and I will be looking at another boat before too long.
Just looking, naturally...
Now, does anybody know where we might find another mooring?
Fair winds,
Tris
BoatFools Sailing — Sailboats for the Rest of Us.
A question for BoatFools Nation:
Have you ever fallen for a sailboat you absolutely didn’t need? Did common sense prevail, or did you end up owning another boat?
And which do you regret more—the boat you bought or the one you let get away?
We’d love to hear your confessions in the comments.




Oh boy!! Thank goodness some people rescue those seaworthy boats. Seaworthiness is a real problem with boats that are manufactured today.
I hope more fools rescue more boats on leaps absolutely not lead by objectivity or common sense... It’s the only way.
We bought a Columbia 56, 1977 3 years ago. The second owner threw an insane amount of money into it. It was insane, I swear. But she now is S42/W96 on her way to Patagonia!