Funny

30 Hilariously Worst Vacation Fails Ever

We’ve all been there. The vacation can just go wrong in every way possible.

Published September 11, 2023

Things can’t always go as planned and this is especially true when it comes to traveling. While taking a vacation from the daily grind is an awesome thing to do, the planning sometimes goes wrong in every way possible. But then, it’s not just the picture-perfect ambiance and food that make a trip memorable. Even the unexpected, which most describe as failure ends up defining the travel experiences and is a reminder that life can be unpredictable.

From being upstaged underwater by a fish during a honeymoon, to a 100-year-old family cabin burned to the ground on the first day of vacation, including being photobombed by a spider monkey in the Dominican Republic, we’ve compiled a list of fails that were frustrating at the time but eventually turned out to be the funniest moment in inventories. Have a look, and if you do have a vacation fail experience, don’t hesitate to share it with us.

#1 “I Traveled All This Way To See This Popular Place, Only To Be Disappointed.”

30 Hilariously Worst Vacation Fails Ever — artifexlife

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

#3 “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?”

#4 “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.”

#5 “We Got Photobombed By A Spider Monkey On Vacation In The Dominican Republic.”

#6 “Someone’s About To Have A Fun Vacation.”

#7 “The Soles Of My Shoes Fell Off In The Middle Of The Forest While I Was Hiking.”

#8 “My Friend Was Trying To Take A New Profile Picture In Front Of A Waterfall.”

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

#10 “I Went To See The Famous Neuschwanstein Castle, And This Was Our View.”

#11 “I Reserved An Airbnb With A Sea View. I Can’t Complain.”

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

#13 “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.”

#14 “She Was So Excited About The Romantic Amsterdam Canal Tour That She Couldn’t Sleep The Night Before.”

#15 “Perfect Way To Start The Honeymoon.”

#16 “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.”

#17 “My Friend Tried To Take An Underwater Photo Of His Wife During Their Honeymoon.”

#18 “Long Kayaking Trip And Belly Rolls Make The Most Inconsistent Sunburns Ever.”

#19 “I Went To The Top Of The Eiffel Tower For The View.”

#20 “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.”

#21 “The View From My Hike Yesterday.”

#22 “Wife And I Took A Trip To Los Angeles.”

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

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

#25 “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.”

#26 “100-Year-Old Family Cabin Burned To The Ground On The First Day Of Vacation.”

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

#28 “We Wanted To Take A Picture Under Water, But Dory Photobombed Us.”

#29 “She Just Wanted A Cute Picture But Got This Instead.”

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