Not-So-Smooth Sailing: 40 Hilarious Boating Fails

Well, would you look at that! This boat decided to play with fire in the middle of all that water – talk about irony. We’re not sure how it managed to turn into a floating inferno, but it did, and we’re scratching our heads here.

Hopefully, everyone evacuated in time. We mean, come on — surrounded by water, you’d think they’d have the upper hand in the firefighting game. But judging by the pic, that upper hand is not as good as we thought it should be!

Okay, seriously, picture this: you’ve aced the sailing rules, mastered water safety like a boss, and secured your boat to the dock like it’s a piece of art. Then, out of the blue, Mother Nature drops a couple of hefty seals onto your precious vessel.

Imagine strolling down to your boat and discovering these blubbery buddies casually sunbathing on top of it. Do they even realize they’re turning your boat into a submarine? Or are they just enjoying the view from their unintentional floatation devices? Either way… What a bizarre moment.

Hold the phone! Check out this topsy-turvy speed boat bursting out of the water, kicking its passenger to the curb. It looks like the tables have turned, and now the poor human is switching places with the boat…

Although, with the boat in the air like that, we should rather call it a small plane! The boat’s on a gravity-defying joyride, but one thing is for sure: you don’t want to be underneath it when it decides to make a splashy return to reality.

After a long day on the water, there’s nothing like sitting down at the local pub and having a nice cold one. But most of the time, people park their boat and then walk into the pub. This guy had a different idea!

Can you imagine what it must have been like to be sitting in the restaurant and seeing that boat coming at you? We can, and we’re pretty sure that there was some colorful language used!

One of the main reasons people get into boating is to get away from all the stress in their lives. For some, that means heading out into the waters by yourself to get a little alone time. However, we’re not sure that this is the type of alone time this guy was expecting.

Not only does he look like he is in deep contemplation, but he definitely looks like he’s a little annoyed with the situation. Hopefully, someone is on their way to help this guy out before the rest of his boat sinks.

We know that back in the day, sailors liked to bury their treasure, but this is a little ridiculous. How did this boat wind up in such a state? And how did the sailor that was driving it allow this to happen?

Still, there’s some silver lining — at least they were able to make land and weren’t stuck out in the middle of the ocean. That would have been even more frustrating and dangerous. Plus, this way, the boat is easily recovered!

There was clearly some partying going on here because otherwise, they would have seen that gigantic rock looming on the horizon. It definitely looks as if someone wasn’t paying attention and is now paying the price.

We’re not quite sure how to fix this problem — but we’re guessing that hopping offboard, climbing onto the rock, and pushing isn’t the answer. We’re not sure if the yacht found its way back into the water, but we hope that everybody was safe and that the boat wasn’t too damaged.

Who knew boats could fly? Not this pontoon boat, that’s for sure! We really can’t work out how exactly this happened. Maybe it had something to do with the storm and the wind picking it up, or perhaps it was a mishap with a crane. Either way, this is not the way to store your boat after a long day on the water.

We’re sure that this boat was uninhabited when it found its new home in this spot. If not, that would have been one heck of a ride and one heck of a story for the person onboard. Sheesh!

So close yet so far away! That’s probably what this person was thinking as they attempted to get their boat into port. That being said, at least it was a leisurely swim for them to get to the land safely, right?

We wonder how long it took them to get to land and how much bailing of water was required. At least it looks like it’s going to be an easy fix, unlike some other situations that have taken place out on the open waters.

We would be utterly furious if we showed up at the dock to hop on our boat and go out for a day on the water, and this is what we found. Who didn’t call them, or who wasn’t paying attention to those security cameras and allowed this to happen?

There are only two upsides here — the first is that the boat was tied to the dock and easy to find. The second is that there was likely no one on the boat that could’ve been hurt. Although, if there had been somebody on board, maybe this wouldn’t have happened. Hopefully, they can get it turned right side up and back in working condition pronto!

We hope that this tugboat wasn’t actually towing anybody into port at the time this happened because that would mean this is actually a picture of more than one boating fail. Even if they weren’t towing someone else in, though, it’s still a sad state of events.

What do you do when a tugboat goes down? Do they send another tugboat? If they do, the captain and the people on the tugboat that’s sinking will probably get made fun of. We don’t know what the protocol is, but we would really like to find out!

One of the most important things to keep in mind when you’re out on the water is to keep an eye on where you are. Even if you’re having a great time and are having a deep conversation like this group seems to be, you still have to pay attention to where the boat is going.

We really do wonder if they realized how close to shore they actually were. It had to be pretty obvious, right? We aren’t experts, but last time we checked, boats didn’t go on sand.

Taking a boat into island inlets, parking up, and having a good time relaxing in the sun is the way that many of us want to spend our days. But what’s happening in this picture is not the same thing. How did this option get a vote?

Truthfully, the only thing we could think of was that maybe the tide was a little higher when they parked the boat. If not, someone needs to get their eyes checked so they can make sure they have good depth perception before they drive the boat again.

This guy really put a lot of work into building his new, um, boat. But why did he do it? That would be the question we would ask ourselves. Perhaps his real boat had a little accident, and this was what he could salvage from the remains. Or maybe he doesn’t have a boat and thought this was better than nothing.

Either way, no matter why he chose to create this new boat, he definitely looks very pleased with himself. He even went so far as to do a little bit of painting with the cool writing on the tires as a way to set his new boat apart from the others. Float on, brother!

Spending the day on the lake fishing and just relaxing is the way a lot of people like to spend their time off. But typically, the boat is in the water because that is where the fish are. This guy doesn’t seem to understand that.

We do have to give him a little bit of credit because he got very close to where he should be. The good news is that he took the time to take a little picture of his catch of the day… although it looks a lot like his boat to us!

This boat captain was either trying to jump over the barrier, or they just thought that they were in a Hollywood movie trying to look very cool. But unfortunately, it didn’t wind up being cool at all.

We hope that the guy on the four-wheeler is there to help. With a simple push, this boat would be all ready to get back out on the water where it’s meant to be.

Transport ships typically get stacked or loaded in specific ways. The loading people know what they’re doing, and there’s no doubt that it’s going to make it from port to port. This ship, however, seems to have had a new guy working on stacking and loading it – that’s the only explanation we can think of for this mess.

It must have been frightening for bystanders (byboaters?) when they saw this container ship start to tip over. It’s good it wasn’t a cruise ship or passenger ship and that the only thing that’s going to be lost is some material goods. On the flip side, that’s a lot of money that’s going to be emptied into the harbor. We hope they have insurance!

Typically, you only have to worry about parallel parking when you’re driving a land-based vehicle. But this guy thought he’d give a little shout-out and try to do it in an aquatic vehicle. It’s not a bad try for the first time… If he meant to end up on the side of the mountain, that is!

Adding insult to injury is the fact that it looks like he’s going to need someone to come help him get the boat down. What could be worse than failing with a boat? Fellow boaters seeing your fail and having a laugh at your expense.

Bringing your boat to the lake for a water outing is always a great way to spend a morning or afternoon. Those who don’t keep their boat at the lake itself have to transport it in some way, which usually means towing it with their vehicle.

We don’t know if this person had ever taken a boat to the lake or not, but someone should have told them that this was not the way to go. After all, somebody had to have been watching as they were doing this. Note for the future – keep the wheeled vehicles on land!

We don’t know about you, but we’re pretty positive when someone docks their boat, they assume it’s going to be safe while it’s parked. After all, they tie it up, they get it all set up, and it should float there peacefully, right? It is a boat, after all.

But clearly, we’re wrong! The waves must have been pretty epic to sink this boat like that. We’re sure the guy is upset, but hopefully, he was able to get it out of the water and drained without too much of an issue.

Grab the rope and start pulling! If we arrived at the docks and saw that our boat was precisely where we left it… except now underwater, we would freak out. How this happened and how someone didn’t see it happen is beyond us.

Of course, it could be because there was no one monitoring the boats when it happened, but surely people noticed it after the fact? It’s not unspeakable, but it’s definitely a big fail because the hole had to be pretty big for that boat to take on that much water. How come the captain didn’t see it before he left? Hmmm.

We don’t know whether to call this a fail or to be very impressed. Parking your boat on the side of a lake or river and securing it should mean it’s safe and sound. Sadly, that was not the case and this boat got itself into some trouble.

Because they’re so close to the water, if they really pulled really hard, they could get the boat out of the water and drained. Yet again, we’re left scratching our heads in confusion about how something like this can even happen.

When you get a boat, the first thing you want to do is name it something awesome. If it’s a retirement boat, “No Worries” seems like the perfect name for it. But “No Worries” is not really living up to its name, at least in this situation.

We wonder how many times the guys who were trying to help save the boat kept talking about the no worries thing. There are clearly worries, and someone should have paid attention. Lesson learned, and next time, name it something a little different. This is Murphy’s Law at its worst.

How fast was this guy going when he plowed on those brakes at the stoplight? He had to be going pretty fast for his boat to jump over the top of his truck and land on his hood. This is going to cost a pretty penny to fix.

But even more embarrassing is the fact he has to sit there in this intersection, waiting for someone to come to help him remove his boat from his truck. This is a facepalm moment if we’ve ever seen one!

No matter how you try to look at this, it’s clear that something went wrong. While we aren’t boating experts, we know for sure that boats aren’t meant to have water in them. And it’s definitely past the point of bailing the water out!

Even though this is an epic fail and this boat seems to be lost to the water, it looks like it wouldn’t take too much to get it out of the water. The question is… how on Earth did this happen? And how can the owner stop it from happening again?

It has to suck to sit there and take a picture as you watch your boat slowly be eaten by the waves, not only because we’re sure this guy loved his boat but also because that’s a lot of money going under.

What happened? Who knows! But one thing’s for sure — it’s going to take a lot for this guy to get over this fail. At least he got off the boat and didn’t have to float around waiting for help.

When we look at this picture, all we can think is that this person’s day was ruined for sure. Clearly, on the way to having a good time, the boat decided to take a little trip of its own. It’s got to be a nightmare not only for them but also for others on the road.

Most boat owners take a lot of pride in looking after their boats. So, we can only imagine the sinking feeling (no pun intended) when this boat fell off its trailer on the freeway. Sorry, pal, it just wasn’t your day!

There’s so much wrong with this picture. First, the fact that the cops are there on the phone trying to figure out what to do, and second, the guy who’s supposedly there to help get the boat off the dock is posing like this is his vacation to Cancun.

It’s got to be frustrating and dangerous to be in this situation. We’re not sure how or what went on to get that boat up there, but we’re fairly certain that the person who did it is going to take a little time away from the water.

Honestly, we don’t know a lot about boating. But we do know that, typically, you don’t try to back the boat up over the dock. But that’s what it looks like the person was trying to do here, and it just didn’t seem to work out. Also, the docks here are super close, so the driver needs to be extra careful.

A lot is going wrong, and unfortunately, this guy just happened to be in the wrong place at the wrong time. We’re not sure how this fail happened, but we think it calls for better planning.

A boat is an aquatic vehicle made for use on bodies of water. Looking at this picture, we’re wondering if maybe our concept of what a boat is has been wrong all along because it looks like the boat is hovering.

Luckily, it’s just an optical illusion because what’s really happening is much less intriguing… It’s just some speed demons driving their boat so fast that it’s leaping out of the water. Remember: safety first, always!

The fact that the owner of this boat decided to tie it up to this pylon is something that we’re not sure should have been done. That being said, at least they know exactly where it is, and nobody’s going to take it.

Our minds are rife with questions: what exactly happened? How did the pylon wind up in the middle of the boat? Where is the owner of the boat? And why did they take the time to tie the whole boat to the pylon? Guess we’ll never know.

One of the joys of being out on the water is that there’s not a lot of traffic to be had, which means that there are fewer accidents that occur, right? Well, apparently, we’re wrong because accidents do happen.

This person was not prepared for this one… or were they? We wonder what drove this person to do this. It definitely feels like something that may have been intended. Maybe they got distracted for a second. You know what they say – don’t text and boat!

The weird thing about this picture is that this road looks like it’s made of water. Maybe there was some flooding, or maybe it’s the way the light’s reflecting. Either way, it looks like this guy thought, why not just take the boat out for a ride? All jokes aside, though, clearly someone lost their load on their way through this tunnel.

The traffic that a fail like this will create has got to be frustrating. They clearly had no idea how to ensure that their boat stayed on the trailer, and that was the biggest mistake in this whole situation.

What do you do if you want to do a little fishing out on the lake but don’t have a trailer to take your boat? Well, if you have a small enough boat like this, you could always pop it in the trunk and say a little prayer that it stays put.

However, we’re not sure they really thought it through because we might have chosen to strap it to the roof as opposed to trying to put it in our trunk. It doesn’t quite fit, and it feels like it could be a traffic and safety hazard.

We would hate to be the owner of this boat. If we had a boat that was this cool and then it sank like this, we’d definitely be frustrated and a little annoyed at the whole situation. Boats are meant to float, aren’t they?

Hopefully, someone will come along soon to help them get their boat out of the water. We’re sure that he’ll laugh about this situation one day, but today is not that day.

What happened here? It looks like this person’s day on the water ended on a sad note. The only thing we can say is that it definitely would be a better day if they at least got their fish out of the whole situation.

After all, if you’re on the lake all day trying to catch some fish to take home and fry up, and your boat goes down like this, you want to get something out of the day. Man, oh, man, we feel this boat owner’s pain!

We’ve all done it — looked at a parking spot and thought, oh, we can get in there, only to find out that it’s a little bit of an ill fit. Right, we think that’s what happened in this situation. Well, except for the fact that the person decided to park their boat on a rock!

There’s probably going to be a hefty fine in this guy’s future for parking his boat near a walkway. We aren’t sure what happened here, but we can tell the owner of this boat is not happy. We wouldn’t be either.

We’re not really sure where to start with this one. Well, who doesn’t want to have more room on their boat? After all, more space means you can have more people with you. But this is not what we had in mind.

Is this supposed to be a unique transportation device, or is it just simply them trying to get the bus from one island to the other? Whatever the answer is, it looks like a recipe for disaster. Maybe we’re wrong… who knows?

Looking at this boat, you see all of the little doodads on top that clearly show that it has an excellent navigation system. But apparently, that navigational system has one component that doesn’t quite work right, and that’s the human component. This person was clearly not paying attention to all his little guides and gadgets; otherwise, he would have seen this giant rock right in front of him.

It does look like he did a good job of parking it, so there shouldn’t be too much damage. Hopefully, no harm came to any passengers. But in the end, this is not going to go well when the rest of his sailor friends learn what happened.

Remember when your mom and dad used to tell you to make sure you tied knots securely so you didn’t lose whatever you were tying up? That whole lesson should have been translated to this boat and its transportation. But it wasn’t. And, sadly, this is what the guy had to deal with.

We wonder if he’s on the phone with his wife right then, and if he is, what type of conversation is it? Either way, we’re sure he’s not feeling too good about himself, and he’s probably getting an earful!