The 10 Ugliest Sailboats Ever Made

Because Not Every Boat Was Blessed With Good Looks

Beauty may be in the eye of the beholder—but let’s be honest, some sailboats push that theory to its breaking point.

Over the years, designers have chased interior space, cost savings, performance, innovation, or pure ego, and sometimes the looks were the first thing tossed overboard. That doesn’t mean these boats are bad. Many are seaworthy, comfortable, and have crossed oceans.

But ugly?

Oh yes.

Below is a brutally honest, sailor-approved list of the 10 ugliest sailboats ever made, including mass-produced boats and infamous one-off yachts that actually sailed.

This time, we’re starting with the least offensive… and ending with the boats that cause sailors to audibly groan at the dock.

#10 — Dufour Atoll

A Floating Apartment Complex With Sails

The Dufour Atoll attempted something bold: giving a monohull the interior volume of a catamaran.

It succeeded—at a cost.

Tall sides, boxy shapes, and a deckhouse that feels more architectural than nautical make it one of the most visually controversial cruising boats ever built. It’s innovative, spacious, and frequently described using words that don’t belong in polite company.

Comfort won.
Aesthetics surrendered.

#9 — C&C Mega 30

Fast Boats Can Be Ugly Too

C&C built many beautiful performance boats.

The Mega 30 was not one of them.

Designed to be trailerable and competitive under rating rules, it ended up with flat sides, awkward proportions, and a stubby cabin that looks bolted on as an afterthought. Even owners admit it’s frequently nominated for “ugliest sailboat ever built.”

Speed forgives many sins.
But not all of them.

#8 — Buckler 24

So Ugly It’s Almost Impressive

The Buckler 24 packs a wheelhouse, ketch rig, and motorsailer layout into just 24 feet.

That should have been a warning sign.

The result looks like a bathtub wearing a hat. It’s tall, awkward, and wildly out of proportion. Critics have mocked it for decades, though a small group of fans insists it’s practical.

They may be right—but they rarely claim it’s attractive.

#7 — Atlantic Clipper 36

The Pirate Ship Nobody Asked For

The Atlantic Clipper 36 tried to combine classic styling with modern comfort.

Instead, it looks like a theme-park pirate ship.

High freeboard, oversized stern, and exaggerated details give it a cartoonish presence. Some find it charming. Many find it horrifying. Almost everyone agrees it’s… a lot.

Comfortable inside.
Strange outside.
Unforgettable either way.

#6 — Westerly Vulcan 34

Practicality Taken Too Far

The Westerly Vulcan 34 is a prime example of function steamrolling form.

Its deck-saloon cabin rises like a bunker on a relatively short hull, giving it an awkward, top-heavy appearance. From some angles it looks like it’s wearing a helmet. From others, like something went very wrong at the factory.

It’s a solid, capable boat.
It’s also famously described as “impossibly ugly.”

#5 — Far Harbour 39

Designed to Fit in a Box… And It Shows

The Far Harbour 39 was designed to fit inside a standard shipping container.

Mission accomplished.
Beauty not included.

Long, narrow, and nearly vertical-sided, it resembles a floating fence post more than a yacht. Every curve was sacrificed to meet container dimensions. Even the designer admitted aesthetics were never the goal.

It sails better than it looks—but that’s a low bar.

#4 — MacGregor 26

A Sailboat With an Identity Crisis

The MacGregor 26 refuses to choose sides.

It’s part sailboat, part powerboat, and part philosophical argument. With water ballast, a massive outboard, high freeboard, and a bubble-shaped cabin, it looks wrong to traditional sailors from every angle.

Innovative? Absolutely.
Practical? For some people.
Good-looking? Not even close.

#3 — Morgan Out Island

The Floating Condo That Launched a Thousand Liveaboards

The Morgan Out Island is legendary—and not because it’s graceful.

Wide, tall, boxy, and utterly unconcerned with elegance, this boat was designed for charter fleets and liveaboards long before “liveaboard lifestyle” was trendy. Sailing performance took a back seat to space, comfort, and shallow draft.

Sailors mock it.
Liveaboards love it.
Photographers avoid it.

It’s the sweatpants of sailboats: ugly, comfortable, and unapologetic.

#2 — Bayliner Buccaneer

When a Powerboat Company Tried Sailing

The Bayliner Buccaneer exists because someone at Bayliner said, “How hard can sailboats be?”

The answer turned out to be: very.

These boats prioritized low cost and interior space above everything else. The result was slab sides, awkward proportions, and window placements that looked random at best. From a distance, they resemble floating RVs that accidentally sprouted masts.

Owners defend them for affordability.
Sailors judge them on sight.
Marinas never forget them.

🥇 #1 — Sailing Yacht A

When a Superyacht Decides It Hates Sailboats

Let’s end where controversy peaks.

Sailing Yacht A might be the most expensive sailing yacht ever built—and also the most divisive. Designed by Philippe Starck, it looks less like a sailboat and more like a floating sci-fi fortress.

The inverted bow, flat gray hull, narrow slit windows, and towering carbon masts make it feel cold, aggressive, and deliberately anti-yacht. Traditional sailors recoil. Tech billionaires applaud. Everyone stares.

It’s a marvel of engineering.
It’s revolutionary.
It’s also widely called the ugliest sailboat ever launched.

⚓ Final Thoughts: Ugly Boats Still Sail

Here’s the uncomfortable truth most sailors won’t admit:

Ugly boats cross oceans.
Ugly boats get loved.
Ugly boats create unforgettable memories.

In many cases, ugliness is simply comfort winning an argument with tradition.

But if we’re being honest?

Some sailboats were never meant to be photographed.