Sink or Swim: The Most Hilarious Boat Fails We’ve Seen on the Internet

By: Kate Row | Published: Nov 02, 2022

We have to appreciate the bravery of these sailors but having non-experts behind the wheel is a recipe for disaster. Combine that with the dangers of the open sea and you end up with boat fails like these ones.

From sunken ships to fiery crashes, these are some of our favorite boat fails that have been shared across the internet. Check them out and be grateful you’re not in the same position as these poor sailors!

Boats Go in the Water and Trucks Stay on the Road

Our friend might have things a little turned around. Typically, boats go in the water, but it looks like he wound up with his truck in the water instead. Cars might be able to survive rain and snow, but they definitely can’t survive submerged in water.


Source: endeared

And, they’re not going to be much use to you in the water anyways. Getting the boat into the water is difficult even for the most experienced boat owners, to be fair. But we can’t imagine how they thought this was a good solution to that problem.


Moments Before Disaster

This image is taken from a YouTube video that went completely viral. Can you take a guess at what happens only moments after this still image? We’ll give you a hint. None of them end up standing at the end of it.


Source: outdoor hub

It looks like they hit a wave or a sandbar and everything goes wrong from there. Almost everyone on the boat winds up horizontal and no one stays dry. It’s the price you pay for a fast speed boat ride.

Flying Boat

Boats aren’t supposed to fly but here one is, flying. It looks like the captain of this boat isn’t concerned with the fact that the bat is in the air. They’re having the time of their lives.


Source: fuel curve

Not to mention, it’s not even really over the water. When gravity pulls that boat to the ground, we’re not sure it’ll survive. It made for a cool picture, at least.

Man Overboard

Rule number one about being on a boat is don’t go overboard unless you want to be fish food! This guy obviously didn’t get the memo because he is way overboard. But, he managed to hang onto the boat.


Source: far wide

You may notice it’s not his arm that holds onto the boat, it’s his shorts. That’s got to be one major wedgie. His friends are laughing so we hope he’s alright.

Intersection Crash

There are no red lights and green lights on the open sea, but this picture might be an argument for them. This driver didn’t understand that there is still traffic in the water, just like on the roads!

Source: Pinterest

Or maybe they were trying to use this other boat as a launching pad to infinity and beyond. We can only hope no one was hurt. Even the cleanup crew looks confused as to how this accident might have occurred.


Going Down Under

This boat looks like it just came from the sky and is going to plummet to the bottom of the ocean. The only problem is that’s not a submarine so it’s not going to work underwater.

Source: cruisers forum

It’s sure going to make a big splash and a big dent in the bank account, unfortunately. Hopefully the owner has insurance on the boat.


Into the Eye of the Hurricane

When it comes to boats versus the ocean, our bet will be on the ocean… always. It looks like these guys are proving our position here. One guy is hiding in the boat hoping to not be rocked too hard by the wave.

Source: far wide

His friend is abandoning ship! And he looks to be diving right into the eye of the storm. We aren’t sure who has the right strategy here. I don’t know if that boat is going to survive a wave like that.


Private Island

I think this guy might be lost, or maybe he’s just at a loss. I don’t think I would know what to do if my car was submerged like this either. I have to wonder how he got on the hood as well.

Source: trends in the boating and maritime sectors

Poor guy is going to have to bite the bullet and hop in the water at some point or else he’s going to go down with the cra. This is further proof that cars are not boats. That island isn’t going to last long.


Wind vs. Boat

Sailors know how to work with the wind to make their boat fly across the sea. But if you make one wrong move, your boat might end up in a position like this. 

Source: dockwa blog

You can see that the sail has already dipped into the water so that boat is most likely a goner. Those guys are trying their best to save it but we think they probably ended up in the water not too long after this photo was taken.


Look Behind You!

If you’re going to spend time on the water you need to be aware of your surroundings. The saying “Keep your head on a swivel” really applies here but these guys didn’t seem to get the memo.

Source: far wide

They’re much too focused on whatever they might have on the hook to see the waterfall they’re about to take a joyride on. The real question is, “How did they not hear the rushing water?”


A Boat is Anything That Floats

If your definition of a boat is anything that floats, then this little contraption is technically a canoe. We have to applaud the creativity for this one because it looks like this little refrigerator is working!

Source: twitter

He had a paddle and everything. It looks like he hasn’t taken on any water in the freezer or fridge compartments so we’re not even sure if we can call this one a fail.


Discount Prices

We’re all for a bargain but this has to be a joke! Imagine seeing that a boat was half off online and then when you arrive this is the so-called “boat” that is for sale. 

Source: kingman yacht center

It’s half price because it’s half a boat. But, just like a dollar bill cut in half, it has absolutely no value. We can’t imagine someone being able to make this float. We have to give credit to whoever tried to sell it, though.


Into the Wild

This pair is certainly a brave bunch. They’re riding right into the eye of the storm with seemingly no fear. They must have overestimated the size and power of their boat because that is not going to end up well.

Source: boating magazine

We would be incredibly impressed if they made it through this wave without landing in the water. We can’t imagine they were in great shape after a crash like this.


Up Up and Away!

Tubing is fun but when the tube ends up in the air it can be awfully scary. There is a reason that there is a difference between parasailing and tubing. Tubes aren’t made to fly.

Source: motor boat yachting

But this one certainly did take flight. These guys don’t look too concerned with their friends who have turned into a giant kite. We hope they landed safely in the water.


Lean Back

Boats like these need some weight distribution or else you’re going to end up underwater. These guys just don’t seem to care. We are guessing this boat went tip up in the air and the motor went under soon after this was taken.

Source: wide open spaces

They might be lounging now, but they probably weren’t as happy when they had to swim back to shore. Bye bye boat!



We wish we had the backstory on how this boat ended up ramming into this house. Was it attached to a truck and got released? Was it on a crane? Whatever the case we wonder if the owner of this boat is the same owner as the house.

Source: motor boat yachting

If that’s the case, they’re going to have to spend a lot of money on roof repairs as well as boat repairs. One thing is for sure: This is an expensive accident.


Winnie the Pooh is Abandoned

Whoever owned this boat has not been the owner for a long time. It sees this one has been abandoned for quite some time judging by the rust. But, you can still make out that it was once called “Winnie the Pooh”.

Source: flickr

We don’t know how Winnie ended up shipwrecked on this shore but we hope whoever was on it is safe and sound. This was probably a beautiful boat in its hay day.


Head First

Oops. We’re not sure how this man ended up going  head first into the ocean. We can guess that it had something to do with a boat turning too fast. Going head first into the ocean off a boat is scary on its own.

Source: updated news

But it’s especially scary when you dive headfirst towards the propeller! We hope that he ended up safe so we don’t feel too bad laughing at this boat fail. Maybe he tripped on his flip flops.


Jet Skis Are Boats Too

If you don’t have a boat, but you still want to go fishing, fear not! The jet ski is coming to the rescue. But, look at the size of that fish! We can’t believe that it didn’t pull these guys under.

Source: pinterest

We must admit, we’re impressed they were able to catch a fish that big with nothing but a reel, a jet ski, and a cooler. That’s talent!


Cruisin’ For a Bruisin’

This guy looks like a professional athlete so we’re sure he knows how to get himself out of this situation safely. But we must admit it’s a good action shot.

Source: itboat

In a fight between this man and the wind, the wind won, which is usually the case. If you squint he kind of looks like a seagull, right?


Perfect Parking Spot

This is another example that has us completely confused as to how this boat might have ended up here. We have to assume that a crane dropped it here. Or potentially the tide was high and then when the water went out this boat ended up atop this rock.

Source: far wide

Maybe we’re just being pranked. We can’t be sure but it is just another reason we don’t own a boat. How would you get it down from there?


Let Her Do the Work

This man is the definition of “living your best life”. He couldn’t be more relaxed. Lounging with a cigar in hand while his lady does all the work for him. However, we could see one problem arising.

Source: far wide

That boat is tipping like a see saw and we think that cigar might be underwater soon enough. Thatmight put an end to this peaceful boat ride.


The Splitz

This is exactly what happens when you untie the boat a little prematurely. When the boat is untied, we know that you need to hop on quickly. That boat will float right away without you!

Source: youtube

This man waited just a second too long to climb aboard and now he’s stuck in the splitz. We hope he’s flexible or else this will certainly be a pulled muscle. At least he’s holding onto that cooler with a tight grip.


Double Parked

This is another expensive accident. It looks like a giant came in and placed the boat on top of that truck. While Toyotas can take a lot, we think this might test its capacity.

Source: far wide

Boats belong in the water, not on top of trucks. Hopefully they were able to get the boat off and into the water where it belongs with minimal damage.


Drag Racing Disaster

This isn’t the kind of crash that happens everyday. This is an intense wreck from a drag boat. These tiny boats can have up to 10,000 horsepower so you can only imagine how intense a crash can be.

Source: pdn

Crashing into anything at 270 mph is harsh, let alone hitting another boat going that speed! We hope everyone is safe and sound.


Sitting, Waiting, Wishing

This poor man is stuck on his own island with nothing but his thoughts to occupy him. He probably has a lot to think about. “How much is this boat going to cost me? Should I replace it or am I done with the ocean forever?”

Source: imgur

“What is my wife going to say?” Luckily, it looks like there are people around to rescue the poor guy. The bad news is they probably also saw his little accident firsthand.


Staying Grounded

It looks like someone probably ran this boat tinto the ground and decided to abandon ship (literally). Over time it sunk right into the ground like quicksand. Now, it’s less of a boat and more of an in-ground pool.

Source: imgur

The real question we have about this photo has nothing to do with the boat at all. Are those horses walking along the beach?


Safety First

This man doesn’t look too concerned considering he is on a sinking ship. In fact, he’s sporting s huge grin despite his boat going under. At least he has safety on his mind.

Source: imgur

Hopefully that life vest will keep him from going under with the boat. Maybe he’s not concerned because it’s not his boat, but someone else’s instead.


That Doesn’t Go There

Something doesn’t fit quite right here. We can understand that transporting a boat is difficult to do. But this certainly cannot be the best solution. We’re not sure how they came up with this idea.

Source: imgur

We’re even less sure how they executed the plan. We have to assume that their trunk is completely broken now. But maybe it was worth it to get that boat out onto the water.


Like a Boat on Fire

We’re happy to see that no one is on this boat on fire. This one is a little more scary than funny considering how dangerous a boat on fire is! But it almost takes a kind of skill to catch something on fire that’s surrounded by water.

Source: imgur

Hopefully, the fire was quickly put out and everyone got to safety. We don’t know who’s in charge of footing the bill though.


Stuck In the Mud

This guy has gone fishing but we don’t think he’s going to catch many fish in that mud. More likely, he will catch a few worms, or nothing at all.

Source: imgur

It looks like he might just have to wait for the tide to rise again to get out of this pickle. Or else he needs super strength to push the boat out of the mud.


Side Splitter

The only thing worse than a boat fail is a boat fail that ruins not one, but two boats. Maybe this person had a personal vendetta against the other boat because this went right into the side as if with a vengeance.

Source: imgur

That poor boat got split right into two and didn’t even stand a chance. This is definitely not the good kind of side splitter. I’d hate to have been the person who had to inform that boat owner of this accident.


Flying Solo

This boat didn’t want to be hitched to this wagon anymore so it slid right off the back. We have to just hope that there were no cars behind the trailer so the boat didn’t slide off right into another vehicle.

Source: imgur

What we’re beginning to learn is that boats should just stay in the water because a lot of these boat failures happened with boats being outside of the water!


Mountain Climber

This boat had dreams of reaching the mountain tops and gazing out across the water from a high vantage point. But, boats aren’t supposed to scale mountains so it was stopped fairly early in its tracks.

Source: imgur

Thinking of the scratches that must now grace the bottom of this expensive boat make us cringe.