30+ Vacation Fails So Hilarious They Might Just Make You Want To Stay Home

Every traveler dreams of the perfect getaway, but sometimes things don’t go exactly as planned. We’ve scoured the internet and compiled a list of funny vacation fails that will have you laughing out loud.

From unfortunate sunburn patterns to mistakenly booked ‘romantic retreats’ that turned out to be anything but, these hilarious misadventures remind us that sometimes, the journey can be more entertaining than the destination.

So, the next time your own trip doesn’t go quite as smoothly, just remember: you’re not alone, and sometimes the best memories come from the funniest vacation fails.


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”

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

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

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

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

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”

7. “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?”

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

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

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

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

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

13. “My Friend’s Vacation In China”

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

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

16. “Long Kayaking Trip And Belly Rolls Makes The Most Inconsistent Sunburns Ever”

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

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

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

20. “Best Vacation Ever”

21. “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”

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

23. “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”

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

25. “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”

26. “Perfect Way To Start The Honeymoon”

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

28. “100-Year-Old Family Cabin Burned To The Ground On The First Day Of Vacation”

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

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

31. “The View From My Hike Yesterday”

32. ‘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”

Nate

Nate Armbruster

When he's not doomscrolling Twitter or writing for Pleated-Jeans, Nate Armbruster writes jokes—and then tells them on stage as a stand-up comedian, where he can watch audiences (hopefully) laugh in real-time.