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25 Of The Most Seriously Awkward Photos Taken On Vacation

The words vacation and pictures usually go hand in hand. If you visit somewhere on vacation but don't take a picture, did it really happen? Plus, how are you going to tell everyone about your amazing vacation without pictures? If you’re going to spend a lot of money on vacation, you definitely want to remember everything.

Awkward vacation photos are pretty much a necessity of any awesome vacation. Unfortunately, now that we have digital cameras and phones where you can see your picture immediately, we aren’t seeing as many awkward vacation photos. People scan their photos to see if you captured their best side and are able to delete pictures that aren’t the most desirable.

However, before we had all this technology, you took a picture not knowing how it was going to turn out. You couldn’t tell if everyone’s eyes were open or if that shirt made you look bad. You had no idea if everyone was smiling or if there were any photo bombers lurking behind you.

Although some of the vacation photos below have nothing to do with bad timing. Some of them are just plain awkward. Here are 25 of the most seriously awkward photos taken on vacation.

25 Squirrel Photobomb

via: randomfunnypicture.com

I’m not sure what’s weirder than a squirrel photobomb, especially a squirrel who is looking straight at the camera. And is he posing? This couple set their camera up and put it on the auto setting so they could capture a photo of them on vacation in a beautiful location. And then a squirrel wanders over and wants to know what the fuss is all about. The couple is seen with smiles on their faces so they clearly found the situation amusing. But it still makes a great weird vacation photo to show to their friends.

24 Keep All Hands In The Vehicle

via: noteabley.com

It looks like this was one of those drive-thru petting zoos where animals roam freely and are able to walk right up to your car. Before you start, you are usually able to get some food so you can call the animals up to your car and feed them. But it’s anyone's guess how the animals are going to react, or how the kids are going to react either. They will remember to roll up their window next time they run out of food for the animals.

23 AquaFamily

via: today.com

And the winner of the most awkward vacation photo goes to…The Aqua Family! I’m really not sure what’s going on in this photo or where they’re at. It’s usually not the best idea to wear matching family outfits during vacation photos. But does that rule still apply when it’s matching scuba suits? I’m going to say yes, the rule still definitely applies. Next time, maybe they can opt for different color scuba suits to switch it up or even add a little pattern to those suits.

22 Everyone Smile

via: boredomtherapy.com

If you’ve ever taken a family photo with children, you know how difficult it can be. Trying to get everyone looking at the camera is next to impossible and you shouldn’t even think about getting everyone looking and smiling at the camera. And if one or more of the children don’t feel like cooperating, well there’s not much you can do. But as they say in show business, the show must go on! The little boy is still technically part of the family photo so it totally counts.

21 Swing Your Partner

via: noteabley.com

Sometimes a little family stroll down the beach can get out of control. However, figuring out how this can happen is another story completely. The Dad actually took to the internet to explain what exactly happened. They were finishing up their reunion and wanted to take some family pictures. The kids weren’t in the best mood, so they decided to swing their kids around to see if they could improve their mood. But then he looked over and the baby was flying through the air. However, he said everyone was fine!

20 Flipper Fun

via: noteabley.com

This is pretty much the quintessential aquarium photo with the kids. Going on vacation with kids isn’t the same thing as going on a vacation with only adults. You don’t get to stay out all night and you don’t get to lay on a beach all day. A vacation with young kids is filled with museums, days at Disney, and aquariums. However, you don’t know how young kids are going to react. Will they be pumped and want to pet everything or will they not be too excited if a dolphin comes up behind them to say hi?

19 Do You See It?

via: awkwardfamilyphotos.com

Can you imagine going on vacation, getting ready to go sightseeing, and seeing…well, nothing? On top of that, I can only guess by the look on the older son’s face that it wasn’t easy getting him out of the hotel room and on this exciting family adventure. At least the other two are still able to look on the bright side. Do they actually see anything? Either way, at least they made sure to get the picture so they could prove that they were definitely here!

18 Family Photo

via: today.com

Family vacation pictures can take a lot of time and planning. You need to plan outfits, perfect picture place, and most importantly, what pose everyone is going to do. The good thing is, this family didn’t wear any interesting patterns or try to match shirts. The bad news is, the rest of the picture. Hopefully, this was just a spur of the moment pose and no one actually thought this picture through and thought it would be a good idea. However, that’s the only positive of this photo.

17 It's A Train Wreck

via: awkwardfamilyphotos.com

Planning a vacation is no easy task. Every single detail is thought of, down to what each family member is packing in their suitcase. You can try to stay on top of everything, but you can’t make sure everyone will enjoy all the activities you planned. It’s even harder to please everyone if you have a wide range of ages in your family. This is a great example of that. The oldest son doesn’t look like he’s enjoying this particular activity. But if you paid all that money for a vacation, make sure you still get the picture regardless!

16 Does This Color Look Good On Me?

via: today.com

It’s always good to be careful about what colors you wear. Like making sure you don’t wear white to someone else’s wedding and making sure to wear black to a funeral. Oh and here’s another one you can add to your list. Make sure you don’t wear your green “Teenage Mutant Ninja Turtles” T-shirt when you’re on vacation. Especially if you plan on visiting some popular tourist attractions and taking pictures in front of a green screen. The floating head looks pretty awkward, but maybe they’re able to laugh it off.

15 Child Down

via: today.com

Stonehenge is a very popular tourist attraction in Europe and it’s probably on many bucket lists. If you have the chance to go, definitely make sure to capture the moment on camera, even if it’s not the best picture, or the right timing. We're not sure if the little boy tripped or what happened exactly. But judging by the windblown hair of the other family members, it’s possible he was knocked over by a strong wind. Nevertheless, at least they got a picture to remember their time!

14 Mount Rushmore Look-Alike

via: today.com

This photo was clearly taken a few years back and I can only imagine how the kids feel about this awkward family vacation photo now. Maybe they should do one of those recreation photos to really relive the memory. I can only imagine their mother positioning the kids so they’re at the perfect angle and making sure they have the right expression. One thing is for sure, they got the height part of the picture down. So how do you think they did? The resemblance is uncanny, right?

13 The Magic Of Disney

via: today.com

Disneyland is such a magical place. You get to finally meet your favorite movie characters from when you were a child. Then there are all the fun rides and the delicious food you get to eat. What could be more magical? Well, Disneyland might not be the most magical place for everyone, and that’s certainly the case for a couple of these kids. At what age does the magic stop? Hopefully, they enjoyed the rest of their vacation more than they did taking this picture.

12 Go Stand By The Toilets

via: boredomtherapy.com

First of all, where does one go to visit the history of the toilet? And secondly, why would anyone want to go and visit a place where they have toilets of all shapes and sizes displayed? But wait, it also looks like there are toilets from many different ages as well. Seems like an interesting place to stop by and see in the middle of a family vacation. From the looks of the picture, it seems as though the kids are excited and I guess that’s all that matters.

11 Who Called For Help?

via: noteabley.com

When you first look at the photo, it looks like a cute little family photo. Maybe the family is escaping the winter by visiting somewhere warm. They’re excited about being on vacation, maybe even visiting some family friends or just lounging around the beach. But then you look behind the children and notice that there is a police officer and EMT with an ambulance gurney. I’m sure it was purely coincidental, but I’m sure no one wants to look back on their vacation photos and see that they were in the way of the EMTs.

10 Cave Exploration

via: whattheflicka.com

Exploring certain caves can actually be pretty interesting. For example, there are lava tube caves in Hawaii that have a ton of history and interesting facts. There are other caves that get wet and cold and allow you to travel hundreds of feet below ground. However, it doesn’t look at though this is one of those super cool caves. It’s either that, or this family really didn’t want to go on any cave explorations. But at least they made sure to put on their hard hats for safety.

9 Everyone Say Cheese

via: sfgate.com

At first glance, it looks like the stingray came over to photobomb this couple and to sday, “hey”. It’s pretty funny to see a smiling stingray! However, these “smiling stingrays” are actually fairly common and you can get a picture of your own. If you find yourself on a Caribbean cruise, most of them have a stingray excursion that you can sign up for. You can swim with the stingrays and even take a picture with one. There is actually someone holding up the stingray to get the perfect picture.

8 No Pictures Please

via: boredomtherapy.com

It’s easy to forget that photos didn’t always used to be digital. Not too long ago, you took all your vacation photos with a roll of film and had to wait to get them developed before seeing how your vacations pictures turned out. There definitely weren’t any re-dos. Seeing this picture makes you realize just how difficult it was to not see photos after you took them. Either they really didn’t want their picture taken, or this is just a case of bad timing.

7 Vacation To The Landfill

via: boredomtherapy.com

It’s always important to think about safety and make sure to wear your hard hat. Isn’t that what they say when going to visit a landfill on your family vacation? Whether it was a scheduled activity or a spur of the moment visit we will never know. But the first rule of vacation is to always take a picture everywhere you stop or else it didn’t really happen. Even though the kids don’t exactly look thrilled, this was probably a family vacation those kids would never forget.

6 Vacation Souvenir

via: whattheflicka.com

This looks like a cute little photo at first, until you realize that their shirts say, “I survived Hurricane Erin”. If I survived a hurricane, I’m pretty sure my first thought wouldn’t be to make a t-shirt to remember the ordeal. Hurricane Erin took place in Destin, Florida on August 5, 1995 and the damage cost about $700 million. In other words, it was kind of a big deal. I guess if you were stuck in the middle of a hurricane on vacation you would need at least one souvenir.

5 Headless Sandman

via: noteabley.com

While this is certainly an amazingly awkward vacation photo, it must have taken a lot of time and effort to get this picture. If the man on the right is completely buried, they had to dig a hole big enough for him to fit and completely cover him up. And then the woman had to get in the right position to make it look like she had no head! However, they ended up getting the picture perfectly so I guess it was all worth it in the end.

4 Sombrero Fiesta

via: noteabley.com

If this isn’t an awkward family vacation photo, I don’t know what is. After receiving a lot of attention, the mom spoke out about the story behind this picture. She said that her daughters fell in love with Mexico after watching a movie. They would ask her to take them to Mexico on vacation but it was too expensive. Instead, the mom took her daughters to a Mexican restaurant where they received these sombreros. I think it’s clear by the photos that the girls could tell this wasn’t Mexico.

3 Am I Holding It Up?

via: noteabley.com

Let’s see if we can count how many people it takes to hold up the Leaning Tower of Pisa? In their defense, you can’t exactly go see the Leaning Tower of Pisa and not take a picture of you trying to hold it up. If you didn’t take the picture, did you really go? Holding up the Leaning Tower of Pisa is actually not awkward at all. However, what is awkward is when you don’t get the angle exactly right and it looks like you’re holding up, well, nothing.

2 How Do My Robes Look?

via: today.com

There’s probably a list of do’s and don’ts when planning your outfit for your family picture. But in case there is not, let’s go over a couple of rules. Don’t have every family member wear the exact same outfit. Instead opt for coordinating colors to complement each other. Don’t mix a bunch of different patterns. And for the number one rule, don’t wear robes on a beach for your family photo. That’s one of the rules, right? If not, it should definitely be added to the rules in the future.

1 Where's Your Sister?

via: awkwardfamilyphoto.com

Petting Zoos are a popular tourist attraction, especially for families that have children. When you have children you aren’t able to sit by a beach all day and relax. Instead, you need to plan activities to keep your children occupied and relatively happy, such as a petting zoo. But you never know how the children are going to react when large animals are suddenly right in front of them. I guess you also don’t know how the animals are going to react either. But hey, that little boy holding the baby goat is super cute.

Sources: Whattheflicka, Today, DailyMail, Noteabley, Boredomtherapy, Awkwardfamilyphotos, Mommyish

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