Travel Horror Stories: How to Take Away Wonderful Lessons for Traveling Better

Estimated read time 15 min read

Halloween is a great time to tell some real life travel horror stories.  Don’t worry, nothing like a scary movie but still some panic-filled moments that aren’t what you had in mind for your vacation.

The truth about travel is that not all moments go as planned.  Some mishaps can be avoided but many things happen that are completely out of your control.  It’s so much more important to take away a lesson learned.  That’s the only way we can hopefully keep it from being repeated.

I’ve learned a lot of lessons over the years, which is also the reason why I turn into a mother hen on a group trip.  If you ever have the pleasure of joining me, be warned because I will repeat a thousand times things that you should know because I’ve already said them a thousand times.  There will still be someone who said they didn’t see the email, the warning, the disclaimer, or hear it.  

Let’s look at common things that can turn sideways pretty quickly. 

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Travel Horror Stories

Everyone takes road trips at least once in a while because what is easier than getting in the car and taking off? But, do we all do the maintenance necessary when driving our own car?  What about when maintenance wouldn’t have prepared you for the unknown?

4 Bad Road Trip Stories

That time the car just started slowing down on the highway and everything was shutting down on it, so, I happened to exit the highway right at exit 46 in Walnut, IA.  At midnight, with only 2 hotels at the exit and neither had any vacancy which we only found out after walking back and forth across the highway with a 2 year old.  Turns out it was the alternator. Lesson learned – always plan for the unexpected to hit you in the pocketbook.

The fun didn’t stop there, later as we made our way down from Pike’s Peak, we noticed the brakes were suddenly screaming.  Being young and thinking that the car was still pretty new, we never expected any of this to happen on our cross country trip from Chicago to Denver. We wound up having to replace both the alternator and the brakes, plus made about a dozen other financially bad decisions during that trip.  Live and learn, and that was all before cell phones.  Lesson learned – get the free all points inspection before you take a trip.

That time my coolant level indicator light came on so I checked under the hood but didn’t close it well.  I started back on the highway and before I knew it, the hood flew up and bashed my windshield.  I was all alone, 2 hours from home.  Thank goodness, I just calmly drifted over to the shoulder to get out of the way while not being able to see a thing.  Lots of good people stopped immediately to see if I was okay.  Lesson learned – always make sure the hood is latched correctly after opening it.

That one time I returned the convertible rental I splurged in for cruising from the Gulf of Mexico to the Atlantic Ocean across Florida. They immediately said there was damage as I approached the return.  Never had this happen before, it truly felt like a setup because I still didn’t see this undercarriage damage they were talking about.  Didn’t matter, I got billed for it.  Thank goodness for the car insurance coverage on the credit card. Lesson learned: Never rent a car without getting the insurance or putting it on a credit card with coverage. 

Travel Horror Stories: How to Take Away Wonderful Lessons for Traveling Better

4 Flying Travel Stories

Newsflash – not one airline is absolutely perfect, not one.  Every single one will have some disappointment at some time.  For instance, cancellations, lost baggage, and detours happen.  They tend to be completely outside of your control or trip plans.  They historically can happen because of COVID-19, weather/natural disasters, and even because of resource allocation by the airlines.  When it happens, the best thing you can do is spring into action.  

That time my husband’s Southwest flight was cancelled from Kansas to Tampa. So, he was stuck overnight in Kansas after he already returned his car rental and the nearest hotel with availability was at least a 45 minute drive away.  The bright side is that at least, he was able to find another car rental and a room.  When he finally was able to get another flight, it was to Orlando, he took it even though his car was in Tampa.  This creates other logistic issues and expenses for the weary traveler.

That time we were stranded in Chicago for 2 days after our Spirit flight was cancelled and a blizzard was coming.  The first night, we said no problem and immediately booked another hotel (thanks to points!) We knew there was a small window to get out after the first cancellation and waited 6 hours in the airport the next morning with a 3-year-old  and a 5-year-old.  When it started looking like the next flight option was about to get cancelled also, I already had a car rental booked and was ready to head to pick it up as the moans and groans were starting in the lines.  

We drove 20 hours back to Florida through every severe weather alert possible as if the blizzard was chasing us.  By the time we hit Tennessee, there were tornado alarms.  Nothing was sunny and bright until we hit the Florida border.  

That time we arrived in Paris after a delay in Germany with no bags to meet us at the baggage pickup.  We had photo shoots scheduled and none of the outfits planned.  Baggage didn’t show up until the morning we were going to head to Marseilles, 3 days later.  One bag never made it and a courier was trying to deliver it back home in Florida.

That time the plane detoured on a flight from Atlanta to Orlando and stopped in Jacksonville for a medical emergency.  I have at least another 4 personal stories just like these.  Things just happen.

Travel Horror Stories: How to Take Away Wonderful Lessons for Traveling Better

Lessons learned: stay calm, be proactive in your planning so you can react appropriately when necessary. Always have a little extra to lean on whether it’s cash, points, a friend nearby, or something that can bail you out of trouble quickly.  These things are hard to think of in the moment when you might panic.  Your cell phone is your friend: check-in on the app, watch the flight schedule for updates, check for cancellation/rebooking options, & change flights on your own faster on the app. Insurance is so important for helping recoup money spent on unexpected changes.

Hotel Disappointments

That time the AirBNB was NOT where I thought it was.  I’ve seen it a few times where someone thinks the place is closer to the city center than it really is.  And then it happened to me.  The first and last time I rented an AIrBNB, it turned out to be in the neighborhood of my nightmares.  The kind that looks like a movie set for bad ideas with one way into the neighborhood and one way out.  The owner even pretended to not know the internet had issues when I reached out to him about it. He said, “wow, the internet was perfect for one year and now it’s not working?”

Lesson learned: I have always used VRBO or Top Villas, it’s just my preference when I want a vacation rental.  Only book rentals in places where I know the area pretty well, not for first time visits.  If I break that rule, it has to have dozens of good reviews, I read any bad ones very thoroughly, and lots of pics from both reviewers and the host.  

I’m looking at the pictures with a fine tooth comb, does that bed look concave, what do the finishes look like, did they show views from any of the windows, can I see the parking situation, do the bedroom pictures match what’s described, how worn does the sofa look. I do not take this decision lightly. Area is a huge concern, proximity to desired attractions, next cleanliness, and then comfort. And after all that, if I decide to book a rental, there’s also a certain level of acceptance that it may not be ideal, try to be safe, and make the best of it.


That time the vacation rental was exactly where I wanted to be BUT it was filthy.  If you’ve ever looked at the Disney vacation rental market, you have probably heard of Championsgate.  Beautiful community, wonderful features and then I arrived at my ideal 8 Bedroom pool home but it was filthy.  Broken blinds laying across the couch yet towel animals on the bed and in the bathroom.  Weird, right?

So, filthy that I went and bought floor wipes to mop the floors and the pads were soaked with dirt very quickly.  I tried complaining but you know when you’re dealing with one that doesn’t care and you’re not getting your money back so all you can do is clean the place up and be grateful it’s not worse.  It had been cleaned, I watched the cleaners leave.  They just weren’t very good at their job.  

A nice movie theatre style room still had dirty cups in it.  Patio furniture looked like someone had just been sleeping on it with cigarettes and the pool skimmer in the pool.  They didn’t mop, fluff pillows, dust, or anything that resembles true cleaning to me.  Just surface wiping and bedding changes, at least we hoped they did that much.  I went ahead and stripped everything and washed it because I don’t trust after you prove you can’t be trusted.

Guess what, vacation rentals aren’t the only ones that miss spots when cleaning.  From ketchup packets at the RItz to clothing in the Venetian, hair on the floor/ceiling and used soap in the shower at countless other hotels. Dirty shower curtains, cup rings on tables, you name it, it happens.  Who needs a black light when you can see these things in broad daylight?  I don’t even want to know the rest of what I can’t openly see.

That time I hadn’t planned my stay and chose a roadside motel along the way.  This was back when I thought I was adaptable instead of extremely picky until I entered the room and was absolutely disgusted to the point that I refused to stay there.  I demanded my money back immediately.  Turned out to be the type of place that threatens to call the police on you instead of just giving you your money back.  Even when the police get involved, the best a ripoff artist does is to give you 50% back so you go away.

Lessons learned: You don’t have to drop your standards, you have to hold them accountable.  Take pictures, demand a room change or money back, leave the review and use whatever power you have to warn others.  When you can’t change your current situation, you don’t have to sit in the filth either, clean it for you not for them.  AND know what you will or won’t do, then don’t budge.  I will cancel my trip plans is I can’t find a place that I approve of staying in than go somewhere that’ll make me break up with my soul.

Document issues:

As a group trip planner, I try to remind the group of everything and provide solutions when there’s a problem.  Sometimes, it’s an easy fix but there are times when the situation is completely out of my hands.

That one time, someone couldn’t find their birth certificate for an upcoming cruise and couldn’t get to another state to get it in time.  We eventually figured out how to ship it to the pre-cruise hotel and crossed our fingers.  It arrived and you think the story would’ve ended there.

However, we arrived at the port and a couple of people in the same group gave their luggage to the porters but forgot to keep their birth certificates and ID on them to actually get into the port.  By the time they realized it, the luggage had already been moved inside.  They were allowed into the luggage organizing area so they could find their bags and get their documents.  Crisis averted.

There are times that this just does not work out though, there are so many people that forget about documentation from having expired Passports to lost ID.  

Lesson learned: Organize important documents early, have a system for where you will keep it, right down to the type of purse/carry-on bag that will work best during your travels.  Have copies in case it’s lost or stolen.  Renew long before expiration dates, 6 months to 1 year before.  

Cruise Concerns:

There was that one time we were on an excursion in the Bahamas and the other group was attacked by robbers with machetes.  Sometimes, good fortune is with you and not others.

I have seen everything from people getting left as the cruise pulls away to worrying about myself making it back to the port in time during an excursion.  

The best safeguards to avoid this is understanding the time changes and allowing plenty of time to return.  Book with recommended cruise excursion companies or the cruise-sponsored excursions instead of going solo in new unknown places.  I’m all for adventure though so believe me, we have gone solo plenty of times but we always leave room to spare and stick to recommended routes and attractions unless it’s not our first visit.  And even when you do everything you were supposed to, things can still go awry.  Insurance helps soften the blows.

For every time that I thought I wasted money buying insurance because nothing happened, the cost for the insurance was not nearly as great as the losses could have been.  And everytime I had insurance to fix the problem, I was so glad I bought it.

Travel Horror Stories: How to Take Away Wonderful Lessons for Traveling Better

Vacation Safety Tips

These stories were on the mild side of horror, we know it can get much worse than these.  I still probably have another 20 worth sharing.  There are some crazy travel stories that might make you want to just stay home.  Some people have even had their fair share of travel insurance horror stories where something they thought would be covered wasn’t. 

All adventures require some risk.  Isn’t that why we love to travel? We just have to try to safeguard ourselves as much as possible and reduce unnecessary risks.  When our travel time is limited, we have to be the hero and save the story.  

It all becomes hilarious when you recall it later, nothing was as bad as it seemed in that moment.  That doesn’t mean you want to go through it again either.  

10 Tips for Safer Travels

  1. Plan for the what-ifs.
  2. Be organized – renew passports, id, &  memberships early.
  3. Back up plan for lost/stolen documents (know where to get copies quickly, in the cloud, from a relative, etc.)
  4. Stay organized – always put id, keys, and credit cards away after each use in the same place so you’re not searching for it.  Don’t be the person at the airport/hotel/wherever with several bags looking disheveled, you look like a ready target.
  5. Do car inspections before a road trip and any necessary maintenance.
  6. Purchase insurance for even road trips or use credit cards with some protection and travel services included.
  7. Set your watch and be clear you understand time zone changes.
  8. Have a plan for meeting up with your group/party and what to do in case of emergencies.
  9. Thoroughly research hotels and vacation rentals even when highly recommended in order to be sure it meets your personal requirements.
  10. Plan, Prepare, Release, Enjoy.  You’ve done all your homework and you’re ready to handle any unexpected challenges so go enjoy.  Accept when things go wrong AND when they go right.

Did any of these travel stories remind you of that one time that…? Go ahead and share it in the comments!

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