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

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

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#2

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

cakes_123 Report

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#3

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

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#4

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

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#6

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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#7

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

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#8

Someone's About To Have A Fun Vacation

Someone's About To Have A Fun Vacation

KerbolExplorer Report

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#9

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

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#10

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

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#11

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

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#12

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

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#13

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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#14

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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#15

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

#16

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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#17

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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#18

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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#19

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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#20

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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#21

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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#22

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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#23

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

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#24

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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#25

The View From My Hike Yesterday

The View From My Hike Yesterday

heavenstarcraft Report

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#26

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

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#27

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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#28

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

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#29

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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#30

Perfect Way To Start The Honeymoon

Perfect Way To Start The Honeymoon

BootyFista Report

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#31

My Friend's Vacation In China

My Friend's Vacation In China

cheongeh Report

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#32

Best Vacation Ever

Best Vacation Ever

Gemini421 Report

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#33

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

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#34

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

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#35

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

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#36

The Waterfall I Went To See Seemed A Bit Dry

The Waterfall I Went To See Seemed A Bit Dry

strongkhal Report

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#37

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

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#38

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

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#39

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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#40

The Manhattan Skyline

The Manhattan Skyline

CakeFace10 Report

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#41

I Tried To Take A Picture Of The Great Wall

I Tried To Take A Picture Of The Great Wall

hipsterthug Report

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