HomeTrendingHilarious Vacation Fail Photos That Will Make You Cringe

Hilarious Vacation Fail Photos That Will Make You Cringe

We all want to be be able to go on our vacations, take a bunch of photos and have a ton of great memories to bring home. Sometimes it works out that way, other times you end up with a photo that is decidedly not showing off a wonderful vacation. Sometimes the photo you have in your ownership shows a vacation that was a miserable failure, and sometimes these failures can be hilarious. That’s why we’ve brought you this list of 10 photos showing the worst vacations ever. Now check them out and tell us if you’ve ever had one go worse.

Sometimes you need to look where you’re going. And then there are times you should never, ever look down. We really want to know how this photo was taken. Also, wasn’t she scared that she would ACTUALLY fall? Even for a funny photo, I’m not sure if I would be able to do this.

We’re more concerned about the pup in this picture! Poor guy was just trying to have a good beach day, and instead was almost flattened by his owner. This just wasn’t fun for anybody involved. We just want to know if the dog is okay! We also wonder if anybody else saw this go down.

It appears the people who want their luggage in this pile are going to be spending a while at the airport. Perhaps their entire vacation. We have so many questions about this suitcase version of Jenga! How were they even able to stack them like this without any of them falling? Who thought that this would be a good idea?

This is what happens when you try a little too hard to show off. We just hope her back is ok! Trying to do tricks when there’s water involved isn’t always recommended, and this is exactly why. We’re also feeling a little second-hand embarrassment seeing as she seemed so sure that she was going to clear this back flip.

Of course, it’s been 30 years and the guy who got puked on still isn’t laughing. Could there be a worse way to spend a day on vacation? We hope he bought this one and hung it up somewhere. Sure, it’s not fun for the girl sitting next to him, but it’s definitely going to have some great memories attached to it.

This is basically everything that could go wrong during a proposal. The girls face behind him is absolutely priceless unfortunately, that ring probably had a hefty price. The soon-to-be bride probably feels awful seeing as she’s the reason the ring fell into the lake in the first place. We really hope he didn’t have to buy a new one, but let’s be honest……will he actually find that tiny ring in that lake?

The guy thought he was going to just chill in the sand and enjoy the day. We’re willing to bet his enjoyment ended 2 seconds after this photo was shot. What he thought was going to be fun, immediately turned into a bad idea. He just really needs to keep his mouth closed until someone comes to dig him out.

No matter how many times we watch this, we still cringe every time she hits the ground! But we just have on question, WHY?! Why would anyone try this. Also, why bring a ball like that to the beach, and why did she think the ball would be able to hold her? We wonder what the people around her thought of this debacle.

This photo is a vacation fail and it’s an awkward family photo. Why in the world would the adults think it was a good idea to match their clothes to their kids? Like we get it, it’s cute or whatever. But they kind of remind us of a traveling circus group. If you think dressing the family the same is a good idea, we’re here to tell you it might look a little ridiculous.

This is why there are rules in place when it comes to running in places where water is involved. This could’ve been avoided if this guy had just taken a second to think this through. This is also why alcohol and boats don’t really go together well…..

People tend to take vacations to get away from it all. These kids got a little sex education for their trouble. We also think it’s hilarious that the family decided to take a sweet family photo in the background! Yup! This one’s definitely going on the mantel!

Just what in the world were they doing that they didn’t think they needed any sunscreen? Gonna be a while before they feel better. The sun isn’t a joke people! If you’re one of those people who claims, they “tan and don’t burn.” Do your skin a big favor and just put sunscreen on anyways. It’s those people who claim they don’t burn who end up looking like this.

We wonder what was going through this guy’s head while he was thinking this through. What was he trying to accomplish with this idea? There’s no way this couldn’t turn out bad! Sure, it’s funny now because he didn’t get hurt! But this definitely could’ve turned out bad.

This picture actually seems like a pretty big vacation success. We just wonder when it’s going to turn bad. Are we not going to point out that the monkey is wearing little bathing suit shorts? I also want to know how this photo came about, because that kid looks weirdly comfortable hanging out with a monkey and a parrot.

You couldn’t pay me any money to jump off of that sketchy little bridge. We just hope it didn’t hurt as much as it looked like it did. We hope the girl behind her decided not to go through with it after seeing what happened to her friend. She also probably got a bunch of splinters.

If there was ever a time to drop the camera and help the kids, this would be it. This doesn’t seem like a fun camping trip. This easily could’ve turned out pretty bad, but naturally, the photographer thought it would be best to just snap photos while a bear approaches.

Honestly, the water was probably freezing, so she definitely had the right idea in mind…..up until she fell in herself. We bet the videographer was dying of laughter. It’s also hilarious because the girl certainly thought she would be having the last laugh, and thought she had devised the perfect scheme…Unfortunately for her, she wasn’t really paying attention to where she was going…

She’s also going to be having some serious nightmares. We like the young girl in back who doesn’t appear to really be in the mood. This is the renaissance fair taken to a whole new level. We wonder how that guy got into that costume, and if it was tough to walk around in?

See, this is exactly what kind of shenanigans end up getting people hurt. This is exactly everything you’re not supposed to do in a pool. But, for some reason, we can’t stop watching because we see something new every time. It looks like the guy literally just threw her in the air without really looking to see where he was throwing her.


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