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

Image credits: cakes_123

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

Image credits: fishhead36

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

Image credits: thirdtimesacharm_

#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

Image credits: ArmitageShanks3767

#5 She Just Wanted A Cute Picture But Got This Instead

Image credits: Bennyheartssports

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

Image credits: Im_The_One

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

Image credits: welcometoross

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

Image credits: viperhauler

#9 Someone’s About To Have A Fun Vacation

Image credits: KerbolExplorer

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

Image credits: BustersHotHamWater

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

Image credits: dat-random-word-here

#12 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

Image credits: RedBanana99

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

Image credits: TheOnlyToast

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

Image credits: Aliendude51

#15 100-Year-Old Family Cabin Burned To The Ground On The First Day Of Vacation

Image credits: Bumper216

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

Image credits: audiwark

#17 Perfect Way To Start The Honeymoon

Image credits: BootyFista

#18 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?

Image credits: Strupnick

#19 My Friend’s Vacation In China

Image credits: cheongeh

#20 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

Image credits: flippity_dippity_doo

#21 The View From My Hike Yesterday

Image credits: heavenstarcraft

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

Image credits: pepsi_next

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

Image credits: a_typical_guy-14

#24 Wife And I Took A Trip To Los Angeles

Image credits: JoeWinchester99

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

Image credits: LoveWineNotTheLabel

#26 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

Image credits: malinda_ferko

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

Image credits: Cappie117

#28 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

Image credits: lucasmcazelli

#29 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

Image credits: fireball_cooper

#30 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

Image credits: manu805

#31 I Reserved An Airbnb With A Sea View. I Can’t Complain

Image credits: weully

#32 The Manhattan Skyline

Image credits: CakeFace10

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

Image credits: FarfetchdSid

#34 The Waterfall I Went To See Seemed A Bit Dry

Image credits: strongkhal

#35 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

Image credits: transient13

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

Image credits: _toro

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

Image credits: couldentcareless

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

Image credits: w11

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

Image credits: Im_Nawt_A_Cawp

#40 Best Vacation Ever

Image credits: Gemini421

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

Image credits: JaMarcusHustle

#42 I Tried To Take A Picture Of The Great Wall

Image credits: hipsterthug

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

Image credits: Tekki

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

Image credits: Daymanic

#45 When You Are On Vacation And The Keypad Lock Stops Working. Then You Try To Access The Door With A Mechanical Key, And That Also Breaks

Image credits: baldy74

#46 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

Image credits: SolsticeSon

#47 I Just Spilled A Full Cup Of Orange Juice All Over Myself On The Last Day Of Vacation. I Didn’t Bring An Extra Pair Of Pants

Image credits: PhilJ223

#48 I Reserved A Suite Months Ago For A San Diego Vacation, Only To Find Out During Check-In That The Pool And Spa Are Closed For Renovation

Image credits: Cool-Swordfish7223

#49 I Went On A $6000-Trip To Japan Last Year, And Took A Photo Of My Friend With Mt. Fuji

Image credits: CuriousityChrissy

#50 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

Image credits: MythicalAce

#51 I Forgot To Fuel Up Before A Long Trip Through Rural Pennsylvania. I’ve Just Barely Made It To The Nearest Gas Station. I’m Screwed

Image credits: DELAPERA

#52 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

Image credits: K00bik

#53 German Tourists Drove All The Way From Germany To Norway Just To Get Stuck In The Parking Lot Next To A Glacier

Image credits: Sverren3

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

Image credits: youngpotato307

#55 What We Expected And What We Got. I Guess I Won’t Be Seeing That Beautiful Norway Scenery

Image credits: kkday218

#56 My Four Friends And I Are On Our Way Home From A Road Trip 1200 Miles Out

Image credits: Sporatious

#57 Great Start To My Vacation

Image credits: Top_of_Descent

#58 First Day On Vacation And Our Half Of The Hotel Doesn’t Have Power. Guess Who Might Be Going Home Early

Image credits: Destined2Pixels

#59 My Phone Fell When I Was At The Grand Canyon

Image credits: hydrohalogenation

#60 Expectation vs. Reality Of “Once In A Lifetime Vacation Destination”

Image credits: Sofa_King_Chubby

#61 That Time I Went To London And Finally Got To See Big Ben

Image credits: axnu

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

Image credits: artifexlife

#63 My Friend Went To Visit A Bamboo Bridge And Rice Field In Thailand That She Saw On Google, Unfortunately During The Dry Season

Image credits: reddit.com

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

Image credits: racertant

#65 I Had The Hall Of Mirrors In Versailles “All To Myself”

Image credits: balram_bahadur

#66 Expectation vs. Reality Of Trolltunga, Norway. Also Not Pictured: The 4 To 5 Hour Long Strenuous Hike To Get There

Image credits: pandemican

#67 A Few Years Ago I Traveled More Than 7000 Miles To See The Grand Canyon

Traveled from Australia to Arizona, and arrived just in time for Hurricane Rosa.

Image credits: roare

#68 Here Is What The Floating Torii Gate At Miyajima Looked Like When I Was There

Image credits: baquea

#69 I Wanted To Visit My Family But Had To Postpone My Trip For 2 Weeks. I Had To Book A Cruiseferry To Get There, But It Ran Aground, And Now I’m Stuck On This Ferry

Image credits: NewViking

#70 The Images Used To Promote Tourism In Rio vs. When I Went There During My Vacation

Image credits: reddit.com

#71 First Day Of My Month-Long Tour, And My Hotel Is On Fire

Image credits: haydenkristal

#72 What A Great View For A Vacation Destination

Image credits: v_approves

#73 I Fell Down The Stairs At A Ski Rental House Right After Arriving. I Broke The Railing And Badly Hurt My Right Hip. Now We Will Have To Pay The Security Deposit On Top Of That

Image credits: Angelic-Guardian

#74 I Went On A Hike To See Fossils And Someone Cut Them All Out

Image credits: Energetic-Potato

#75 The Final Day Of My Vacation With My Fiancee. We Did A Whisky Tasting, And Mid-Way Through, I Realized I Cannot Smell Or Taste Any Of The Samples. I Got Covid

Image credits: MontyMolecular

#76 I Walked 18km To See A Waterfall, And This Is What I Saw

Image credits: rakorako404

#77 A Few Years Ago, We Hiked A Mountain For The View On The Foggiest Day Imaginable

Image credits: brgr_face

#78 I Went Out On A Boat Without Sunscreen Today, And Now I Have What I Am Calling “The Bib Of Pain”

Image credits: Whitefence227711

#79 I Broke My Foot On Vacation

Image credits: ilovecheese514

#80 My Very Expensive Ocean View

Image credits: jonnycarroll1337

#81 Here’s Me And My Buddy At Mt. Rushmore

Image credits: WorldlyHermit

#82 I Hiked For Two Hours To See These Waterfalls

Image credits: Pikachuzita

#83 I Went Exclusively For The Waterfall

Image credits: CynicalCharles

#84 I Went To See The Arctic Ocean, This Is What It Looked Like

Image credits: aryeh95

#85 Overlook Ahead

Image credits: vachmal

#86 50 Miles Into The Weekend Road Trip

Image credits: PlayPoker2013

#87 From My Recent Trip To Alaska. 5 Years In The Making, Been Wanting To Go Since I Was A Kid. I Rented A Car To Go To Denali, And The Road Was Closed From Wildfires

Image credits: bootsmegamix

#88 I Booked A “Falls View” Hotel Room Facing The Niagara Falls. I Can’t See My View Because Of This Mist

Image credits: daninmontreal

#89 The “Beach View” From Our Rental

Image credits: JJaySmokes

#90 I Drove A Couple Hundred Miles Out Of The Way On Our Road Trip Just For The Four Corners Monument To Be Closed

Image credits: stez9520

#91 I Went On Vacation And Shopped At Macy’s In California. Only To Come Back Home To Ontario, Canada And Realize They Forgot The Security Tag

Image credits: AmnixeltheDemon

#92 I Got Up At 3:30 Am And Hiked For About 4 Hours To See This Beautiful View. Expectation And Reality

Image credits: RosewoodVision

#93 My Chance To See The Eiffel Tower Didn’t Turn Out As Expected

Image credits: Fuzzie8

#94 First Day Of Vacation, And We Got Rear-Ended By A Driver Who Has Fallen Asleep At The Wheel. We Were Only A Couple Miles From Our Cottage After A Four-Hour Drive Up North

Image credits: Financial_Emphasis25

#95 Big Ship Blocking Alcatraz In San Francisco For More Than An Hour

Image credits: hi17734

#96 I Upgraded My Room For An Extra $30 Per Night To Get The Fallsview. Look At This Morning View

Image credits: WestRobertson

#97 I Was Going To Celebrate The Start Of My Vacation, But The Wine Bottle Had Other Plans

Image credits: Candycayne84

#98 Long Road Trip, And My Phone Is At 22%, Only A Few Hours Left

Image credits: Half-PunchMan

#99 Well, This Just Happened. At The Airport To Our Vacation

Image credits: Blackjack_Sass

#100 I Went For A Two-Day Hike, And My Brother Said He’d Pick Up The Water

Image credits: OceanSupernova

#101 On Vacation I Went To Check In, And My Hotel Asked I Come Back In An Hour To Pick Up My Key Card Because My Room Wasn’t Ready. When I Came Back, There Was This Huge Line

Image credits: Canonconstructor

#102 I Was Traveling By Bus On Vacation And Paid An Extra To Reserve Premium Seats So I Could Get Front Seats For The Best View. This Is What I Got

Image credits: MaritimeMuse