35 Times People Had The Worst Luck During Their Vacation
When vacations don't pan out as expected.
Experiences and memories make life truly meaningful, and family vacations create some of our most cherished memories. Of course, holidays often lead to all sorts of adventures—some not so pleasant. As the holiday season approaches, many people are planning their time off and travel plans. But if you find yourself unable to go this year for whatever reason, this gallery of family holiday fails might help you feel better about your situation instead.
Image source: Cbert1980
Image source: jellocore
It can’t be more than 500 sqft.
Image source: Bumper216
Image source: blankblinkblank
Image source: IDontFeel24YearsOld
We were packing for our family trip to Jamaica, and I heard my wife scream upstairs. She just tells me, “I’m not going to Jamaica,” and shows me her passport. Only the main page shown is torn. Nothing else. (The image depicted is after she tried taping it back together.) She dropped it on the bed for a second, and the dog got to it. And she is normally not destructive like that, but despite how annoyed we were, we couldn’t blame her.
After reality had sunk in, I hopped on a call with a passport department inquiring about an emergency passport. They apparently only give them out if there is a death in the family, etc. They searched for appointments nearby, and the only one on the East Coast was in Buffalo, NY, at 8 am the following day. So we changed my wife’s flight, and sent her tour to Buffalo, and got her a 10:45 am flight out from Buffalo to Orlando, then to Jamaica, hoping that it would work. They don’t guarantee that you will get it the same day, but the reviews for the location were surprisingly positive, so we were hopeful. She shows up an hour early, is first in line, and they tell her they can get it the same day, but won’t start printing passports till 10 am. The manager came out and told my wife she should probably change her flight because he can’t guarantee that she will get it in time for the 10:45 flight.
She comes back around 10, sits right, and the woman at the front desk gives a friendly wink to my wife. At 10:15, the manager tells my wife’s passport is printing. Around 10:20-10:25, they hand it to her and she hits the find driver button on the Uber app. She gets picked up and takes the 15-minute ride to the airport. The Uber driver told her he’s driven MANY people who flew from out of state to Buffalo for a same-day passport, and he believed she could make it. Well, she did. Boarding got delayed, but she made it with like 10 minutes to spare and arrived in Jamaica only 3 hours after we did.
It was beyond exhausting!
TLDR: dog chews wife’s passport 12 before flight. Wife flies to Buffalo for the only available appointment, gets her passport the same day, and barely makes her flight to eventually meet us in Jamaica, only a few hours after our arrival.
Image source: ryan_dad_of_3
Image source: Metroid413
Image source: lordfukwad
Image source: Dark_Wolf04
In Cyprus, there is a new law where all non-private beaches are government-owned, and dogs are allowed to walk there.
The beach in front of our summer house is one of those beaches, but unfortunately, our elderly neighbors don’t seem to bother to look at the law when it’s not convenient for them.
I bring them at 6 am, and I always clean after them, so they are bothering absolutely nobody. Just a bunch of old people with nothing better to do in their lives, so they control others.
Needless to say, I’ll continue taking them to the beach, and if they actually follow through with their threats, I’d love to see them fined for wasting police resources.
Image source: give_me_two_beers
Everyone is fine, but day one of vacation is not going as planned. Tire came out of absolutely nowhere and completely shattered my windshield. Picking pieces of glass out of my eyebrows, even. Everyone is okay, luckily (one of the kids even slept through it), but it sucks having to spend hundreds on a new windshield and a hotel room for the night. Luckily, someone can replace it tomorrow.
Image source: BearWar
Image source: stoned_brad
Beach reclamation in progress. Heavy equipment is running right outside our windows 24 hours a day.
Image source: survivorsavedmylife
I’m home now, but this is day 3, and it just keeps spreading. Awesome.
Image source: Additional_Goose_763
Image source: Agent-Foxtrot
Image source: livelove_elbow
Image source: BruciePup
And my front tooth broke. I’m headed to Las Vegas, and thankfully, my sister knows a cosmetic dentist who can fit me in tomorrow. I’m sitting in the Houston airport, drinking a beer, waiting for the last leg of my flight.
Image source: fairchildthings
Image source: Sea_Squirrel1987
Image source: falkenfink
On vacation with my little kids. Long travel across Europe and at night stopped for a night in a hotel in Lille near the train station. Before I went to bed, I considered myself lucky to have found free parking. In the morning, a broken passenger window in our car, and the resulting shenanigans with insurance and police. First time in France in 15 years, and I expected to practice my rusty French on different subjects.
Nothing was stolen, as nothing was inside that was worth it. Just have to deal with the aftermath of the damage.
Image source: ManiacallyReddit
I stepped backwards and tripped. That was honestly it. Pretzeled in the worst way possible.
Image source: James--Trickington
Image source: kittykat47
Image source: ruined_s2k
Image source: DarwinF1nch
On a trip with my family, our bags have been at the Madrid airport for the past week. We’ve called the airline twice a day, and all they say is that there’s nothing more that they can do.
Image source: Wendlynnn
In 17 years, we never took a family vacation except to visit family. Mid-divorce, and I am taking the kids by myself for our first overnight at a waterslide resort (a surprise for the kids - booked for tomorrow). My ex called me this afternoon - my teen daughter dislocated her elbow on a hike. Cast from fingers to armpit. No waterslide resort for us.
Image source: Ingtar2
Image source: ChickenLuna
He had it on him when we were out and about, but didn’t notice it was missing until late at night. We were playing switch with the family back at the rental, so he wasn’t thinking much about it. Decided to track its location and saw it was at the boardwalk we were at. Went back and looked for about 20 minutes in the parking lot. Found it smashed to bits! Had to go to the Verizon store the next day. At least we know what happened to it.
Image source: jackie_j_666
Image source: dnr4wlvs
We knew our neighborhood had some bad storms while we were away. As we turn onto our street, we see this.
Think it can't get worse? They had just listed the home for sale about a week earlier.
Image source: 400cc
Image source: AngloSaxonP
Image source: scubahana
Image source: EggCakes27
Image source: MCGamer1234
I’m in a small town and can’t get them repaired u til I go home in a week… Super glue and tape it is then.
#1 Epic Picture
Image source: Cbert1980
#2 On A Family Trip And This Is The Cabin We Are Sharing With 11 People
Image source: jellocore
It can’t be more than 500 sqft.
#3 100-Year-Old Family Cabin Burned To The Ground First Day Of Vacation
Image source: Bumper216
#4 TSA Definitely Went Through Our Bag, And Did Not Put The Cap Back On My Bottle Of Allergy Pills
Image source: blankblinkblank
#5 Our Dog Chewed My Wife’s Passport 12 Hours Before Our International Flight
Image source: IDontFeel24YearsOld
We were packing for our family trip to Jamaica, and I heard my wife scream upstairs. She just tells me, “I’m not going to Jamaica,” and shows me her passport. Only the main page shown is torn. Nothing else. (The image depicted is after she tried taping it back together.) She dropped it on the bed for a second, and the dog got to it. And she is normally not destructive like that, but despite how annoyed we were, we couldn’t blame her.
After reality had sunk in, I hopped on a call with a passport department inquiring about an emergency passport. They apparently only give them out if there is a death in the family, etc. They searched for appointments nearby, and the only one on the East Coast was in Buffalo, NY, at 8 am the following day. So we changed my wife’s flight, and sent her tour to Buffalo, and got her a 10:45 am flight out from Buffalo to Orlando, then to Jamaica, hoping that it would work. They don’t guarantee that you will get it the same day, but the reviews for the location were surprisingly positive, so we were hopeful. She shows up an hour early, is first in line, and they tell her they can get it the same day, but won’t start printing passports till 10 am. The manager came out and told my wife she should probably change her flight because he can’t guarantee that she will get it in time for the 10:45 flight.
She comes back around 10, sits right, and the woman at the front desk gives a friendly wink to my wife. At 10:15, the manager tells my wife’s passport is printing. Around 10:20-10:25, they hand it to her and she hits the find driver button on the Uber app. She gets picked up and takes the 15-minute ride to the airport. The Uber driver told her he’s driven MANY people who flew from out of state to Buffalo for a same-day passport, and he believed she could make it. Well, she did. Boarding got delayed, but she made it with like 10 minutes to spare and arrived in Jamaica only 3 hours after we did.
It was beyond exhausting!
TLDR: dog chews wife’s passport 12 before flight. Wife flies to Buffalo for the only available appointment, gets her passport the same day, and barely makes her flight to eventually meet us in Jamaica, only a few hours after our arrival.
#6 A Nice Gentleman Asked If He Could Take Our Picture For Us, We Got This
Image source: ryan_dad_of_3
#7 Came Home From Vacation To Find Our Fish Tank Leaked Into My Floor While We Were Gone
Image source: Metroid413
#8 Buddy Came Back From Vacation And Realized He Was Missing A Headphone So He Checked It’s Location
Image source: lordfukwad
#9 This Letter I Get From My Neighbors On The First Day Of Summer Vacation
Image source: Dark_Wolf04
In Cyprus, there is a new law where all non-private beaches are government-owned, and dogs are allowed to walk there.
The beach in front of our summer house is one of those beaches, but unfortunately, our elderly neighbors don’t seem to bother to look at the law when it’s not convenient for them.
I bring them at 6 am, and I always clean after them, so they are bothering absolutely nobody. Just a bunch of old people with nothing better to do in their lives, so they control others.
Needless to say, I’ll continue taking them to the beach, and if they actually follow through with their threats, I’d love to see them fined for wasting police resources.
#10 A Tire Came Flying Out Of Nowhere While Driving To Our Vacation Destination
Image source: give_me_two_beers
Everyone is fine, but day one of vacation is not going as planned. Tire came out of absolutely nowhere and completely shattered my windshield. Picking pieces of glass out of my eyebrows, even. Everyone is okay, luckily (one of the kids even slept through it), but it sucks having to spend hundreds on a new windshield and a hotel room for the night. Luckily, someone can replace it tomorrow.
#11 We Were On Our Way To Arizona For A Family Trip And Then
Image source: BearWar
#12 Our Peaceful Beach Vacation
Image source: stoned_brad
Beach reclamation in progress. Heavy equipment is running right outside our windows 24 hours a day.
#13 What Was Supposed To Be A Nice Vacation Turned Into Me Developing A Chlorine Rash After Swimming
Image source: survivorsavedmylife
I’m home now, but this is day 3, and it just keeps spreading. Awesome.
#14 I Tried Whataburger For The First Time In 20 Years, While In Vacation. Are They Punishing Me?
Image source: Additional_Goose_763
#15 The View From My Bedroom In My Caribbean Vacation Rental, Where I've Been Stuck Literally All Week With The Flu
Image source: Agent-Foxtrot
#16 Road Trip Misadventure
Image source: livelove_elbow
#17 Tried To Open A Pack Of Gum On The Airplane…
Image source: BruciePup
And my front tooth broke. I’m headed to Las Vegas, and thankfully, my sister knows a cosmetic dentist who can fit me in tomorrow. I’m sitting in the Houston airport, drinking a beer, waiting for the last leg of my flight.
#18 Single Cab Truck + Stomach Ache = Disaster
Image source: fairchildthings
#19 Somebody's Vacation Is Ruined
Image source: Sea_Squirrel1987
#20 Adventure Vacations
Image source: falkenfink
On vacation with my little kids. Long travel across Europe and at night stopped for a night in a hotel in Lille near the train station. Before I went to bed, I considered myself lucky to have found free parking. In the morning, a broken passenger window in our car, and the resulting shenanigans with insurance and police. First time in France in 15 years, and I expected to practice my rusty French on different subjects.
Nothing was stolen, as nothing was inside that was worth it. Just have to deal with the aftermath of the damage.
#21 I Broke Both My Ankles And A Wrist On Day 1 Of The Family Vacation. I Was Supposed To Go On A Trip With Friends In Less Than A Month
Image source: ManiacallyReddit
I stepped backwards and tripped. That was honestly it. Pretzeled in the worst way possible.
#22 All My Family Trip Photos And Videos Gone
Image source: James--Trickington
#23 Three Days Into My First Trip To Argentina To Spend Time With My Step-Daughter And Husband's Family And I've Come Down With The Flu And Can't Leave The Hotel
Image source: kittykat47
#24 I Feel So Stupid. Forgot To Have Wifey Put Sunscreen On My Back
Image source: ruined_s2k
#25 “Lost” Luggage Has Been In This Location For The Past Week…. And There’s Nothing We Can Do About It
Image source: DarwinF1nch
On a trip with my family, our bags have been at the Madrid airport for the past week. We’ve called the airline twice a day, and all they say is that there’s nothing more that they can do.
#26 Day Before Our 1st Vacation
Image source: Wendlynnn
In 17 years, we never took a family vacation except to visit family. Mid-divorce, and I am taking the kids by myself for our first overnight at a waterslide resort (a surprise for the kids - booked for tomorrow). My ex called me this afternoon - my teen daughter dislocated her elbow on a hike. Cast from fingers to armpit. No waterslide resort for us.
#27 Booked An Airbnb For Vacation. This Is The View From The Shower. There Is No Way To Cover It Up
Image source: Ingtar2
#28 Husband Lost His iPhone On Vacation. We Used Find My From My Phone And Tracked It To Its Last Location. Found It Run Over
Image source: ChickenLuna
He had it on him when we were out and about, but didn’t notice it was missing until late at night. We were playing switch with the family back at the rental, so he wasn’t thinking much about it. Decided to track its location and saw it was at the boardwalk we were at. Went back and looked for about 20 minutes in the parking lot. Found it smashed to bits! Had to go to the Verizon store the next day. At least we know what happened to it.
#29 Trip Ended Before The Border
Image source: jackie_j_666
#30 Came Back To This After Vacation
Image source: dnr4wlvs
We knew our neighborhood had some bad storms while we were away. As we turn onto our street, we see this.
Think it can't get worse? They had just listed the home for sale about a week earlier.
#31 Found This Camera In My Vacation Rental
Image source: 400cc
#32 When You Plan An Entire Family Trip Around Seeing The Fabled Copper Complaint, And It’s Not There
Image source: AngloSaxonP
#33 Leaving For Vacation Today And Put The Oven To Self-Clean. The Middle Panel Decided It Didn’t Want To Live Anymore
Image source: scubahana
#34 Two Hours Into My Road Trip In The Middle Of Nowhere I Opened My Case To This
Image source: EggCakes27
#35 First Day Of Vacation And This Happens…
Image source: MCGamer1234
I’m in a small town and can’t get them repaired u til I go home in a week… Super glue and tape it is then.DE
Written by
Demilked Editorial
SaaS Review Specialist · Demilked
With 5+ years in the creator, entertainment, and publishing spaces, Demilked shortlists, reviews, and ranks leading tools that actually make your life easier.