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We've all been there. The meticulously planned holiday that suddenly goes wrong in every way possible. A delayed flight causing a mishap of scheduling problems, the unsettling realization that your luggage might be touring a completely different continent somewhere around the world, or that memorable moment when the 'cozy beachfront accommodation' you booked turned out to be a scam on Airbnb. However, these vacation fails, while frustrating at the time, often turn into the funniest stories in our ‘inventory’.

After all, it's not just the picture-perfect sunsets and good food that make a trip memorable. Sometimes, it's the unplanned detours and unexpected misadventures as some would describe them as 'fails' that end up defining our personal travel experiences, reminding us of the unpredictability of life!

#1

I Hiked A Mountain In Hot Weather. A Monkey Stole My Water At The Top Then Proceeded To Drink It In Front Of Me

I Hiked A Mountain In Hot Weather. A Monkey Stole My Water At The Top Then Proceeded To Drink It In Front Of Me

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#2

My Friend Tried To Take An Underwater Photo Of His Wife During Their Honeymoon

My Friend Tried To Take An Underwater Photo Of His Wife During Their Honeymoon

fishhead36 Report

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LillieMean
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'm so jealous. I would immediately hang such a masterpiece in the living room. The best vacation picture ever!

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#3

I Just Got Back From Iceland. I Was Going Through My Pictures And Found The Best Photobomb Of All Time

I Just Got Back From Iceland. I Was Going Through My Pictures And Found The Best Photobomb Of All Time

thirdtimesacharm_ Report

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cerinamroth
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My friend and I went to the Dead Sea and he took the obligatory selfie floating in the water while I fell in a sinkhole in the background. That was a good photobomb!

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#4

She Just Wanted A Cute Picture But Got This Instead

She Just Wanted A Cute Picture But Got This Instead

Bennyheartssports Report

#5

100-Year-Old Family Cabin Burned To The Ground On The First Day Of Vacation

100-Year-Old Family Cabin Burned To The Ground On The First Day Of Vacation

Bumper216 Report

#6

On A Family Holiday To Scotland, We Spent Two Hours Walking To A Famous Cave, Expecting It To Go Underground And Everything. This Is The Cave

On A Family Holiday To Scotland, We Spent Two Hours Walking To A Famous Cave, Expecting It To Go Underground And Everything. This Is The Cave

ArmitageShanks3767 Report

#7

She Was So Excited About The Romantic Amsterdam Canal Tour That She Couldn't Sleep The Night Before

She Was So Excited About The Romantic Amsterdam Canal Tour That She Couldn't Sleep The Night Before

dat-random-word-here Report

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panther
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That was probably the best sleep she had during the entire vacation.

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#8

Wife And I Took A Trip To Los Angeles

Wife And I Took A Trip To Los Angeles

JoeWinchester99 Report

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#9

We Got Photobombed By A Spider Monkey On Vacation In The Dominican Republic

We Got Photobombed By A Spider Monkey On Vacation In The Dominican Republic

viperhauler Report

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LillieMean
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I hate the exploitation of animals for tourism. Oh, poor little monkey.

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#10

We Wanted To Take A Picture Under Water, But Dory Photobombed Us

We Wanted To Take A Picture Under Water, But Dory Photobombed Us

pepsi_next Report

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#11

Long Kayaking Trip And Belly Rolls Makes The Most Inconsistent Sunburns Ever

Long Kayaking Trip And Belly Rolls Makes The Most Inconsistent Sunburns Ever

BustersHotHamWater Report

#12

I Hiked 3000 Feet Of Elevation To A High Alpine Lake Only For A Mountain Goat To Eat My Fly Rod

I Hiked 3000 Feet Of Elevation To A High Alpine Lake Only For A Mountain Goat To Eat My Fly Rod

Im_The_One Report

#13

Someone's About To Have A Fun Vacation

Someone's About To Have A Fun Vacation

KerbolExplorer Report

#14

I Went To The Top Of The Eiffel Tower For The View

I Went To The Top Of The Eiffel Tower For The View

welcometoross Report

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Terran
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I personally know at least three people with similar pictures! Fog seems to be quite common in Paris.

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#15

I Always Pack Digestive Aids For The Holidays. 4 Days Ago, I Had Diarrhea And Remembered I Had Medication. It Turns Out I Brought Laxatives

I Always Pack Digestive Aids For The Holidays. 4 Days Ago, I Had Diarrhea And Remembered I Had Medication. It Turns Out I Brought Laxatives

RedBanana99 Report

#16

My Parents Went On Vacation And Asked This Gentleman To Take Their Picture, But He Was Holding The Camera Backwards

My Parents Went On Vacation And Asked This Gentleman To Take Their Picture, But He Was Holding The Camera Backwards

audiwark Report

#17

I Went Hiking Over The Weekend To Blow Off Steam From The Finals Week And Got An Allergic Reaction From Something. Guess Who Has A Presentation Today?

I Went Hiking Over The Weekend To Blow Off Steam From The Finals Week And Got An Allergic Reaction From Something. Guess Who Has A Presentation Today?

Strupnick Report

#18

My Friend Was Trying To Take A New Profile Picture In Front Of A Waterfall

My Friend Was Trying To Take A New Profile Picture In Front Of A Waterfall

racertant Report

#19

My First Trip To Houston. I Was Very Impressed At How Quickly The Locals Performed Pit Stops. Must Be A Lot Of Nascar Fans

My First Trip To Houston. I Was Very Impressed At How Quickly The Locals Performed Pit Stops. Must Be A Lot Of Nascar Fans

TheOnlyToast Report

#20

The Soles Of My Shoes Fell Off In The Middle Of The Forest While I Was Hiking

The Soles Of My Shoes Fell Off In The Middle Of The Forest While I Was Hiking

Aliendude51 Report

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Draperdorf
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That happened to me. I had to tie them to my feet with my shoe laces and try not to trip over the front of the sole flapping with each step. Fortunately I was only about half an hour from home, but still!! My mum gave me here boots as she never used them, and same thing happened!! Apparently the soles on walking boots perish after a few years!!!

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#21

When Your Rental Car Breaks Down And They Send Out A Tow Truck, But The Tow Truck Breaks Down And Needs Its Own Tow Truck

When Your Rental Car Breaks Down And They Send Out A Tow Truck, But The Tow Truck Breaks Down And Needs Its Own Tow Truck

malinda_ferko Report

#22

On The First Night Of Vacation, We Pulled Out The Sofa-Bed For The Kids But Heard A Loud Crunching Sound. Son's iPhone Fell And Got Caught In Hinges Of The Bed Frame

On The First Night Of Vacation, We Pulled Out The Sofa-Bed For The Kids But Heard A Loud Crunching Sound. Son's iPhone Fell And Got Caught In Hinges Of The Bed Frame

flippity_dippity_doo Report

#23

I Reserved An Airbnb With A Sea View. I Can't Complain

I Reserved An Airbnb With A Sea View. I Can't Complain

weully Report

#24

The View From My Hike Yesterday

The View From My Hike Yesterday

heavenstarcraft Report

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StrangeOne
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Just zoom your camera in the picture and pretend the fog was never there.

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#25

I Traveled All This Way To See This Popular Place, Only To Be Disappointed

I Traveled All This Way To See This Popular Place, Only To Be Disappointed

artifexlife Report

#26

I Went To See The Famous Neuschwanstein Castle, And This Was Our View

I Went To See The Famous Neuschwanstein Castle, And This Was Our View

LoveWineNotTheLabel Report

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Mimi La Souris
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

the advantage of this photo is that you can say you went anywhere in the world

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#27

During Our Honeymoon In Greece, My Husband Had An Accident With A Scooter Going 10 Mph. He Broke His Wrist In Two Places, Dislocates His Shoulder And Got A Concussion

During Our Honeymoon In Greece, My Husband Had An Accident With A Scooter Going 10 Mph. He Broke His Wrist In Two Places, Dislocates His Shoulder And Got A Concussion

fireball_cooper Report

#28

I Visited The Torii Gate In Hiroshima, Japan. What I Was Expecting vs. What I Saw

I Visited The Torii Gate In Hiroshima, Japan. What I Was Expecting vs. What I Saw

a_typical_guy-14 Report

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Cat Chat
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

On the bright side, it looks like it's still there. Possibly it's just being cleaned.

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#29

Perfect Way To Start The Honeymoon

Perfect Way To Start The Honeymoon

BootyFista Report

#30

This Is The Only Photo My Mom Took Of Me And My Dad In Front Of The Liberty Bell

This Is The Only Photo My Mom Took Of Me And My Dad In Front Of The Liberty Bell

Cappie117 Report

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#31

My Friend's Vacation In China

My Friend's Vacation In China

cheongeh Report

#32

I'm On A Motorcycle Trip From Colorado Springs To Las Vegas. I Went South To Avoid The Snow, And Now I'm Stuck In Arizona With Over A Foot Of Snow

I'm On A Motorcycle Trip From Colorado Springs To Las Vegas. I Went South To Avoid The Snow, And Now I'm Stuck In Arizona With Over A Foot Of Snow

MythicalAce Report

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Ezra Varley
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I live in Flagstaff and the 2022-2023 winter has been the 2ed biggest snow fall recorded in Flagstaff

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#33

Best Vacation Ever

Best Vacation Ever

Gemini421 Report

#34

I Broke My Foot In Cancun On The First Day Of My Honeymoon

I Broke My Foot In Cancun On The First Day Of My Honeymoon

couldentcareless Report

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Imreallyjustaghost
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Had a buddy go to Germany. Within the first hour of being there, stepped off a curb the wrong way and broke his foot.

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#35

I've Traveled Abroad And Brought My Drone To Record It. I Hiked To The Top Of This Hill And Realise That I Forgot The Batteries At Home

I've Traveled Abroad And Brought My Drone To Record It. I Hiked To The Top Of This Hill And Realise That I Forgot The Batteries At Home

lucasmcazelli Report

#36

I'm About 1000 Miles Away On Vacation, And This Happened 2 Days Into My Trip

I'm About 1000 Miles Away On Vacation, And This Happened 2 Days Into My Trip

Daymanic Report

#37

I Was Going On A Family Cruise Trip. Flight Got Delayed Three Times, And After All That, The Flight Got Canceled. Now We Missed The Cruise, And Waited At The Airport For 7 Hours

I Was Going On A Family Cruise Trip. Flight Got Delayed Three Times, And After All That, The Flight Got Canceled. Now We Missed The Cruise, And Waited At The Airport For 7 Hours

K00bik Report

#38

I Just Wanted To Shower In My Hotel After A Long Road Trip

I Just Wanted To Shower In My Hotel After A Long Road Trip

Im_Nawt_A_Cawp Report

#39

The Waterfall I Went To See Seemed A Bit Dry

The Waterfall I Went To See Seemed A Bit Dry

strongkhal Report

#40

We Did A Long Half Dome Hike. We Got To The Top And Realized The Guy Who Was Supposed To Pack The Food Packed A Single Sandwich Bag Of 4 Charred Wieners

We Did A Long Half Dome Hike. We Got To The Top And Realized The Guy Who Was Supposed To Pack The Food Packed A Single Sandwich Bag Of 4 Charred Wieners

SolsticeSon Report

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Ron Man
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Why would you go on any type of hike and expect 1 person to bring food for you, and if you did that, why wouldn't you talk about a meal plan or expectations ahead of time? I've been hiking alone and in groups for decades and everyone brings their own items.

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#41

A Photo I Took Last Year vs. The One I Took Today. I Thought I'd Drive And Hike There Because It Finally Snowed. What A Disappointment

A Photo I Took Last Year vs. The One I Took Today. I Thought I'd Drive And Hike There Because It Finally Snowed. What A Disappointment

manu805 Report

#42

Grand Canyon View After Renting A Car And Driving 3.5 Hours To See It

Grand Canyon View After Renting A Car And Driving 3.5 Hours To See It

_toro Report

#43

Expectation vs. Reality Of Traveling 2,874 Miles To See The Cliffs Of Moher

Expectation vs. Reality Of Traveling 2,874 Miles To See The Cliffs Of Moher

youngpotato307 Report

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David A Paterson
Community Member
7 months ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I actually had a win at the cliffs of Moher. It was awfully foggy and dismal but just clear enough to make out the cliff edge opposite. The photos came out extremely dramatic, like the cliffs were falling off the face of the Earth. Better than if it was sunny.

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#44

Day 2/18 At The Resort In Puerto Vallarta For Our Honeymoon, And I Walked Into The Balcony Door

Day 2/18 At The Resort In Puerto Vallarta For Our Honeymoon, And I Walked Into The Balcony Door

FarfetchdSid Report

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VonBlade
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

How fast were you running, and why were you carrying a sack of cement?

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#45

Here Is My Fiancée Fulfilling Her Lifelong Dream To See The Mona Lisa In Person

Here Is My Fiancée Fulfilling Her Lifelong Dream To See The Mona Lisa In Person

JaMarcusHustle Report

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VonBlade
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

"I went to see the worlds most famous painting, in possibly the worlds most popular gallery, and discovered others did too", the post

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#46

The Manhattan Skyline

The Manhattan Skyline

CakeFace10 Report

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Mavis
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Old photo? Or is this plaque still there as a memory for what was lost?

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#47

My Daughter Went On A Boat Trip As A Graduation Gift. The Boat Have Been Stuck In The Mud Since They Arrived Yesterday. They're Supposed To Get Towed Out Today

My Daughter Went On A Boat Trip As A Graduation Gift. The Boat Have Been Stuck In The Mud Since They Arrived Yesterday. They're Supposed To Get Towed Out Today

transient13 Report

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BrookeBT
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

This is why we shouldn't have given the Suez Canal so much media attention - it gave all the little boats inspiration.

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#48

I Tried To Take A Picture Of The Great Wall

I Tried To Take A Picture Of The Great Wall

hipsterthug Report

#49

Took Our 6-Month-Old Labrador On Our First Family Road Trip

Took Our 6-Month-Old Labrador On Our First Family Road Trip

w11 Report

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Bart
Community Member
7 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That one is on you, also very dangerous not to have your dog in a kennel in case of a accident!

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#50

I Forgot To Put Sunblock On My Legs During A Kayak Trip On The Lake

I Forgot To Put Sunblock On My Legs During A Kayak Trip On The Lake

Tekki Report

Note: this post originally had 102 images. It’s been shortened to the top 50 images based on user votes.

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