HomeCultureHilarious Vacation Fail Photos That Will Make You Cringe

Hilarious Vacation Fail Photos That Will Make You Cringe

We Assume This Didn’t Turn to Tragedy

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.

Anything But The Dog!

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.

Mine’s The Blue On On Top

That’s Gotta Hurt

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.

Someday They’ll Look Back On This And Laugh

Proposal Gone Wrong

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?

This is Why You Never Let People Bury You

Mom! Look What I Can Do!

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.

Matching Family


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…..

“You Said There Would Be No Learning On This Trip”

Walking, Talking Sunscreen Commercials

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.

Not Sure If This Is How Parasailing Is Done

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.

Dr. Doolittle In the Flesh

She’s Definitely Going To Feel That Tomorrow

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.

This Might Not Be The Time To Take Pictures

She’s Got The Right Idea

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 Having the Time Of Her Life

Pool Gymnastics?

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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