Nate
Vacations are supposed to be a time to kick back, relax, and make memories that last a lifetime—but not all memories are created equal. Sometimes, instead of postcard-worthy sunsets or flawless Instagram snaps, travelers come home with vacation fails stories so hilariously unfortunate, they deserve their own Hall of Fame. These pictures prove that even the best-laid travel plans can go gloriously sideways.
Here are some funny and unfortunate vacation fails that’ll make you laugh, cringe, and feel just a little better about your own travel mishaps. After all, nothing says “vacation vibes” like an unexpected plot twist in paradise.
1. “A Llama Photobombed My Machu Picchu Pic”
2. “First Vacation I’ve Had All Year And Work Won’t Stop Texting Me… Should I Send It?”
3. “Took This Photo Of The Beautiful Sunrise At Our Bed And Breakfast, Years Ago, During Our Honeymoon. I Didn’t Look At It Closely And Sent To All Of Our Family. Nothing Says ‘Welcome To The Family’ Like A Photo Such As This”
4. “Well Crafted Beach Photobomb”
5. “This Is The One Thing I Am Most Worried About Before Getting On A Plane”
6. “Living/Working In Hawaii, Took A Break To Travel. I Don’t Travel A Lot, But When I Do, Everything Is Under Construction”
7. “My Uncle’s Suitcase After His Flight”
8. “Our Trip To The Petting Zoo Did Not Go As Planned”
9. “The Hotel I Booked Weeks Ahead Didn’t Have A Room For Us When We Checked In. Gave Us A Sofa Bed In A Conference Room”
10. “Drove Quite Awhile To Be Able To See This Waterfall”
11. “2 Weeks Ago My Youngest Daughter Broke Her Leg 1 Week Before Our Holiday. Yesterday I Broke My Own Leg (On Holiday). Poor Sis And Mom”
12. “Taking A Picture With My GF In Berlin, When Out Of Nowhere”
13. “A Beach Day That Turned Into Me Tripping On A Rock And Falling Down The Sand Dune”
14. “Includes A ‘Private Balcony.’ Is Just A View Of The Wall Of The Next Building”
15. “Hiked Two Hours To Set Up A Picnic, Returned To This”
16. “Airbnb Wasn’t What We Were Expecting”
17. “I Drove 4 Hours (One Way) To See Radium Springs, One Of The State Of Georgia’s Natural Wonders . . . After A Heavy Rainfall”
18. “This Is The Result When I Ask My Boyfriend To Take A Picture. Can’t Stop Laughing”
19. “Google Maps Didn’t Tell Me About This After A 2 Hour Drive”
20. “My Trip In Mexico Is Great So Far”
21. “Tire Went Through My Windshield On The Interstate”
22. “I Was On My Way Down The Tallest Mountain In The UK And This Happened”
23. “Paris CDG Airport. Someone Will Have A Bad Day”
24. “Half Way To The Road Trip In Sicily, The Tire Just Exploded Out Of Nowhere. Happened Exactly 12 Hours After I Had Food Poisoning The Night Before”
25. “Lesson Learned- Don’t Trust Just Any Tourist To Take Your Photo”
26. “These Tourists In Hawaii Took A Wrong Turn”
27. “I Have To Travel To Another City Asap And This F***er Decided To Park Its Car Right In Front Of My Garage. It Has Been 45 Minutes And This Is Not The First Time This Is Happening. Still Waiting For The Tow Truck”
28. “Loved My First Trip To Japan. I’m Too Tall For Japan”
29. “Went On Vacation And”
“Went two states away for a weekend trip, were checking out of the hotel to find this. All 4 wheels stolen in the hotel parking lot. Of COURSE the hotel doesn’t have cameras in the parking lot. Can’t get it towed because it doesn’t have wheels to get on the damn truck.”
30. “4 Hours Into A 13 Hour Road Trip To My Family’s 3 Week Vacation Of The Year And I Just Realized That In The Rush To Leave I Forgot To Bring Any Other Shoes With Me”
31. “Just Wanted To Enjoy My Vacation”
“Went on a trip for almost 2 weeks. Started to feel sick 5 days ago and just thought I was dehydrated. Came to the hospital to be told I have a severe uti, kidney infection, and sepsis. My flight home was supposed to be tomorrow. I have no idea when I’ll be able to go home.”
32. “Road Trip To See The Lighthouse”
33. “Where My GPS Indicates The Train Station Is Supposed To Be”
34. “I’m On My Honeymoon”
“Had sushi for dinner last night at the all-inclusive resort my new husband and I are staying at. 1am rolls around and I’m throwing up like crazy, then it’s dry heaving for another hour. We call the resort doctor, he takes my temperature and listens to my belly with a big “oh no” face, so guess who gets to go to a clinic in a foreign land (we’re in the Dominican Republic)? Me!!
I have a bacterial infection in my guts! My white blood cell count is bananas! We get to spend $4000 upfront cuz I need to be hospitalized! Weeeeeeee!
Get Travelers insurance, be better than me. Don’t know what the resort will do but it sounds like they’re willing to work with us.”
35. “My Trip To Bali (Nusa Penida Island). Expectations vs. Reality”
36. “First Day Of Vacation”
“Unfortunately there was someone right behind us and I couldn’t stop it time. Lucky for us the deer jumped and hit mostly glass so no airbags! But it did take out the cargo rack and sunroof and ended up being over 14k in repairs!”
37. “On My Honeymoon In Hawaii And Turns Out I Got Ringworm From The Armrest On The Plane”
38. “This Happened Last Year, Flying Back From Vacation. They Told Us Our Suitcase Must Have Fallen Off The Transport Truck. Everything Inside Was Gone, Yet They Managed To Retrieve The Bag”
39. “I Broke Two Bottles Of Sangster’s Rum Cream While Boarding The Plane”
40. “I Traveled About 1500 Miles To See Fenway Park For The First Time. Here Was My View”
