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 source: cakes_123
#2 My Friend Tried To Take An Underwater Photo Of His Wife During Their Honeymoon
Image source: fishhead36
#3 I Just Got Back From Iceland. I Was Going Through My Pictures And Found The Best Photobomb Of All Time
Image source: thirdtimesacharm_
#4 She Just Wanted A Cute Picture But Got This Instead
Image source: Bennyheartssports
#5 100-Year-Old Family Cabin Burned To The Ground On The First Day Of Vacation
Image source: Bumper216
#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
Image source: ArmitageShanks3767
#7 She Was So Excited About The Romantic Amsterdam Canal Tour That She Couldn’t Sleep The Night Before
Image source: dat-random-word-here
#8 Wife And I Took A Trip To Los Angeles
Image source: JoeWinchester99
#9 We Got Photobombed By A Spider Monkey On Vacation In The Dominican Republic
Image source: viperhauler
#10 We Wanted To Take A Picture Under Water, But Dory Photobombed Us
Image source: pepsi_next
#11 Long Kayaking Trip And Belly Rolls Makes The Most Inconsistent Sunburns Ever
Image source: BustersHotHamWater
#12 I Hiked 3000 Feet Of Elevation To A High Alpine Lake Only For A Mountain Goat To Eat My Fly Rod
Image source: Im_The_One
#13 Someone’s About To Have A Fun Vacation
Image source: KerbolExplorer
#14 I Went To The Top Of The Eiffel Tower For The View
Image source: welcometoross
#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
Image source: RedBanana99
#16 My Parents Went On Vacation And Asked This Gentleman To Take Their Picture, But He Was Holding The Camera Backwards
Image source: audiwark
#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?
Image source: Strupnick
#18 My Friend Was Trying To Take A New Profile Picture In Front Of A Waterfall
Image source: racertant
#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
Image source: TheOnlyToast
#20 The Soles Of My Shoes Fell Off In The Middle Of The Forest While I Was Hiking
Image source: Aliendude51
#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
Image source: malinda_ferko
#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
Image source: flippity_dippity_doo
#23 I Reserved An Airbnb With A Sea View. I Can’t Complain
Image source: weully
#24 The View From My Hike Yesterday
Image source: heavenstarcraft
#25 I Traveled All This Way To See This Popular Place, Only To Be Disappointed
Image source: artifexlife
#26 I Went To See The Famous Neuschwanstein Castle, And This Was Our View
Image source: LoveWineNotTheLabel
#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
Image source: fireball_cooper
#28 I Visited The Torii Gate In Hiroshima, Japan. What I Was Expecting vs. What I Saw
Image source: a_typical_guy-14
#29 Perfect Way To Start The Honeymoon
Image source: BootyFista
#30 This Is The Only Photo My Mom Took Of Me And My Dad In Front Of The Liberty Bell
Image source: Cappie117
#31 My Friend’s Vacation In China
Image source: cheongeh
#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
Image source: MythicalAce
#33 Best Vacation Ever
Image source: Gemini421
#34 I Broke My Foot In Cancun On The First Day Of My Honeymoon
Image source: couldentcareless
#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
Image source: lucasmcazelli
#36 I’m About 1000 Miles Away On Vacation, And This Happened 2 Days Into My Trip
Image source: Daymanic
#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
Image source: K00bik
#38 I Just Wanted To Shower In My Hotel After A Long Road Trip
Image source: Im_Nawt_A_Cawp
#39 The Waterfall I Went To See Seemed A Bit Dry
Image source: strongkhal
#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
Image source: SolsticeSon
#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
Image source: manu805
#42 Grand Canyon View After Renting A Car And Driving 3.5 Hours To See It
Image source: _toro
#43 Expectation vs. Reality Of Traveling 2,874 Miles To See The Cliffs Of Moher
Image source: youngpotato307
#44 Day 2/18 At The Resort In Puerto Vallarta For Our Honeymoon, And I Walked Into The Balcony Door
Image source: FarfetchdSid
#45 Here Is My Fiancée Fulfilling Her Lifelong Dream To See The Mona Lisa In Person
Image source: JaMarcusHustle
#46 The Manhattan Skyline
Image source: CakeFace10
#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
Image source: transient13
#48 I Tried To Take A Picture Of The Great Wall
Image source: hipsterthug
#49 Took Our 6-Month-Old Labrador On Our First Family Road Trip
Image source: w11
#50 I Forgot To Put Sunblock On My Legs During A Kayak Trip On The Lake
Image source: Tekki
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