Regretful Travelers Share Their Most Expensive Travel Mistakes

Regretful Travelers Share Their Most Expensive Travel Mistakes

I don't know about you, but before I travel I check and double check every detail. I make sure I have enough money, make sure my phone doesn't ensure roaming charges, make sure I know exactly when to arrive at the gate. If you're going to invest time and money in seeing the world, you'd better get to actually see it. And, of course, mistakes made while traveling can very expensive.

These folks learned that the hard way. Their blunders while on the road not only inconvenienced them but also forced them to pay even more money out of pocket.

These are the most expensive travel mistakes as shared by the people of the internet. Are you sure you have your passport and your money belt?

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20. Never Drink On A Layover

On my way to Russia via Korea for the World Cup with a friend, we drank too much on the layover in Korea. Then my friend had a seizure on the way to the airport in the morning, resulting in us having to rebook our flights on to Kazan and having to use international roaming on our phones to sort out our travel insurance and calling the airlines in both Korea and Russia to see where our bags went.

All in all, it cost us about $4,000. My card also got skimmed in Nizhny Novgorod for an extra $1,500.


19. Unsafe

When my new wife and I arrived at the airport to go on our honeymoon to Bali, the person at the check-in counter said, “I’m sorry but you can’t board the plane. Your passport is only valid for three more months.”

We were confused, as the honeymoon was just going to be two weeks.

“Yes, but Indonesia requires you to have a passport valid for six months before you can enter the country. You aren’t allowed to board the plane.”

We had breakfast at the airport and went back home. That’s how I learned you should renew your passport before it gets down to less than six months left.

Later, the second most expensive mistake came after we finally made it to Indonesia. The first night I drank the hotel’s welcome drink, which had ice in it made from unsterilized water. I subsequently spent much of my honeymoon on the toilet. That’s how I learned not to trust even ice cubes in countries with dodgy sanitation.

Oh, and once I was supposed to go to Brazil. I got to the airport and the person checking me in said, “Where’s your visa?”

“Visa?” I replied. “Yes, you need a visa to go to Brazil.” Well, I didn’t have one and it takes 5 days to get one, so the trip was a total loss! That’s when I learned to check whether you need a visa to go to a country that you’ve never been to before. (This is more of a problem for Americans and Europeans, who don’t need a visa for most countries -- but do need a visa for some.)

One time I forgot to empty out the safe in my hotel room. Fortunately, that wasn’t so expensive; I called the hotel, told them the combination, and had them put everything in an envelope and put it in a taxi to the airport. It turned out okay as this was Britain and people are pretty honest, plus I had gotten to the airport early so there was enough time for the taxi to get there.

(In my defense I had just learned the night before that a friend of mine had died, so I was disturbed and distracted.) After I got back to the office I made a printout with huge font 74 letters in red saying “Empty The Safe Deposit Box!” and laminated it. I put that laminated paper in my suitcase. Now when I go to a hotel, I take the sign out of my suitcase and put it somewhere prominent. I haven’t made the same mistake since.

Marshall Gittler

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18. You Really Need To Check, Guys

I was going to Vietnam with a friend of mine and I asked her if we needed visas, as she's been before. She said no, and I didn't think anything more of it.​

Somehow I'd forgotten she's Korean and, while Koreans don't need a visa to travel to Vietnam, Americans like me do. She ended up going by herself, and I was out the cost of a plane ticket. Stupidest mistake I've made while traveling, but I definitely learned a lesson.

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17. Singapoor

Singapore. Ahhhhh Singapore.

My most expensive mistake was in Singapore. It was a simple computer error that continues to cost me to this day.

I’m considered a planner. I create spreadsheet itineraries and color code them, just to keep everything straight. Usually I’m spot on. This time… I was not. It was a simple error to make. I messed up the equation that converts time zones.

We were on a tour bus tootling around in Little India (Singapore) when I went to check the notes on the printed copy of my itinerary to see where we were going next.

I suddenly realized that the time for the flight out the following night didn’t look correct. I was carrying my tablet and checked quickly just to make sure and realized that we were flying out in about 3 and a half hours. That's when I had a mini meltdown.

We had to ditch the tour (they dropped us off as close as they could) and then catch a taxi the rest of the way back to the hotel to grab our bags and head straight to the airport.

I lost the night at a super nice hotel in Singapore, We missed out on two Singapore tours and a day and a half of time. We missed out on going up to the top of the Marina Bay Sands Hotel…

…and of course, we had to book and pay for an extra pile of stuff when we got to New Delhi. It would have been even worse if we’d missed that flight.


I meticulously checked the itinerary over when we got to Delhi. (We had an unexpected free day given we weren’t supposed to be there yet.) Even worse? I’d done it on the other side after India when we were supposed to get to Hong Kong as well.

A simple spreadsheet error that cost many, many, lots.

That wasn’t the most expensive part. It is very rare for me to make this kind of error. The most expensive thing is: When my partner wants to irritate me, he just points out - “Hey, do you remember that time when you messed up our itinerary in Singapore?”

Michelle Steele

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16. What Happens In Iceland

Stayed out drinking in Reykjavik till 4 AM when I had a 10 AM flight to Amsterdam the next morning. Missed my scheduled bus and had to pay for a taxi from my hostel to the airport. Cost $150. Would’ve been cheaper to just reschedule the flight. Mistakes in Iceland aren’t cheap.

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15. You Have To Chase Them

My husband and I had saved up and paid $1800 for an all inclusive Jamaican vacation. A place I had longed to visit.

I completed all the necessary paperwork and sent for my passport months in advance. In the interim I was busy being a working mother and wife. We planned to join other couples we knew in Jamaica for a blast. The waiting was so exciting.

This was only the third big vacation we’d taken since we had been married. I was so looking forward to the rest and fun. The other couples we were meeting were especially fun and warm people. Good eggs.

Then about six weeks before departure I realized I hadn’t received a response from the State Department. I went online to discover it should arrive that week. My husband already had his from an earlier foreign trip.

The week passed. Still no passport. Two weeks passed. I thought, surely it will be here in time. I called and was told there was a delay because my name had changed but it should arrive within 7–10 working days. What?!! I explained I had a non-refundable trip already paid for, to no avail.

I started counting the days. Hoping for the best but expecting the worse, I calculated the end of ten working days would be the week of the trip. That Monday to be exact. Then I became nervous. Murphy’s law popped in my mind. This can’t be happening.

I was on pins now. Waiting and hoping each day. Nervously rifling through the mail. Looking online for any additional info on passports. Reading about travel tips and hacks.

Now we’re at the last Monday before the trip. Friends are checking in. Everyone’s excited. Me, not so much. I don’t dare say anything. That would be a total buzzkill.

Now it’s Wednesday before our flight. I’m trembling as I rifle through when I get home from work. Still no passport. I call the State Department. They said to go online, make an appointment to go to their office in LA. That’s a sixty mile trip, one way. I make an appointment for 1:00PM the next day which is Thursday. Our flight leaves Friday, early. I have one day to sort this.

Thursday is my last shot at a long awaited vacation. I called our travel agent that night to explain our situation and ask her a lot of ‘what ifs’. She had a fit. I should have called her sooner, she said, she would told me to go to the State Department office weeks ago. Oh man. I’m sunk. This. Cannot. Be. Happening.

Next day, Thursday, I’m up early. I planned to be their hours before my appointment, hoping to be seen earlier.

No such luck. My husband and I sat in this humongous room, filled with people, crying babies and cranky toddlers, all day long, waiting our turn. We were finally called at exactly 5:00 PM.

Up we go, to the window, only to be told I needed a certified copy of my birth certificate to get a same day passport. But I sent your office the certified birth certificate! I must’ve screamed.

My husband asked if there was anything else we could do. He explained our flight left the next morning and the original application for the passport was sent in months ago. She said, she saw online, that the application was in delay because of a discrepancy in the name and that I would need a certified copy of my birth certificate to get a passport today. I’m wilted. I cannot believe this is actually happening. It can’t be.

I asked why didn’t they tell me that on the phone when I called? Shrug….mumble. I explained again, as calmly as I could, that I had sent my certified copy to the State Department, months ago. Silence. She stares at the computer.

I asked, ok what can I do now? She said get another certified copy and bring it in. But I was not born in LA! I can’t just trot over to the LA Hall of Records. I was born in San Diego (another 160 miles) and now it’s too late to even go there because the office is closed and our flight leaves early tomorrow. Sorry. There was nothing she could do. We give up.

Now, I realize the building is empty. We’re the last to leave. Our steps echo as we walk out, defeated and exhausted.

I forced my husband to go. At least we wouldn’t lose all our money. He said he enjoyed seeing new sights but it wasn’t the same. Besides he felt like the third wheel being the only single person. It was basically a bummer but he tried to make the best of it. My travel agent felt sympathy for our situation. She gave a partial refund which I used to help fund my daughter's European tour. A college graduation gift. So all was not lost.

My passport came in the mail the next day. That’s life.

Marie O'Day

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14. DIY

I bought a van with a ton of rust, and instead of taking my welder's advice and cutting my losses I continued to build it out for travel anyways. I probably put somewhere around $10,000 into the van, repairs, and upgrades. Travelled and lived in it for about 5 months and eventually sold it for $300 after I got sick of repairing everything.

I'm incredibly grateful I got to go on that trip and that part I don't regret, but I should've either kept the van basically stock to save from wasting money or gotten a better van as a base so I would've been willing to keep it.

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13. Watch Your Backpack

Riding a motorcycle into Sihanoukville, Cambodia, I got a bit lost and pulled over to check my GPS on my phone. I had my main pack strapped to my bike but was wearing a smaller day pack on my back. I got off the bike and sat down on a nearby bench to check my phone.

It was hard for me to sit wearing the bag, so I took it off and put it on the ground beside me. After figuring out what direction I needed to go, I loaded back onto the motorcycle and headed down the road. Within a few minutes, I felt the air going up the back of my shirt which was a new feeling. I realized that I had left the backpack at the bench. I spun around and raced down the road to find it was gone. Inside that bag was the following:

The ownership for the motorcycle (can no longer sell it), vaccinations card, International Drivers Permit, passport, $200 in cash, Acer computer, GoPro camera and 64gb card, Canon camera and 32gb card, 1TB Western Digital portable hard drive, chargers and cables, Columbia rain jacket, north face hiking boots, drivers licence, tripod for camera, extra batteries for GoPro and Canon cameras, and 3 Snickers bars.

I was gutted. I had 6 weeks of great photos and riding footage that I had not backed up to the cloud yet. All in, it cost me about $2,000 Canadian to replace everything, but I'll never get those memories back. I also got stuck in Phnom Penh for 3 weeks waiting for my passport to be replaced.

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12. At Least She Said Yes

Not a mistake, per se, but I had a secret trip all planned, with hostels, Airbnb, flight, etc. all booked for an 8 country whirlwind tour through Europe and Morocco, culminating in a short stop in France, where my girlfriend was going to be. I planned to show up unannounced and propose to her there.

Long story short, her travel partner couldn't make the trip, and she wasn't keen on traveling alone, so I pretended that I didn't already have a huge trip planned, got refunds on as many flights and bookings as I could, and spent a lovely two weeks in France, which ended with her saying "YES!" It was a heck of a lot more expensive than I anticipated, but very worth it.

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11. Never Put Anything In The Pocket

I left my 3-month-old cell phone in the rear pocket of my plane seat. I realized about 5 minutes after I was off the plane, but they wouldn’t let me back on board to get it. They claim they looked for it and it wasn’t there (yeah, right). Travel insurance wouldn’t cover it because I had let it out of my care before it was stolen. The police didn’t want to know about it.

My first wife had a similar experience… she was checking into a hotel in Fiji and put her “fanny pack” on the counter at the hotel’s reception to give them her passport as ID. When she turned to get the bag it had vanished, along with all her cash… nobody saw anything (yeah right).

What did I learn? It doesn’t matter how tired you are, or how excited to be in a new place, etc. Set up a system (this goes here, that goes there, always the same, every time) and stick to it. You can’t afford to “just set something down for a minute”, if it’s not in your hand and in use it goes back in it’s correct place. And if you do lose something while travelling, never admit to having left it behind to the insurance company.

Matt Lansell

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10. Why Would You Think That?

Driving to Disney with a girlfriend one spring break and thinking we could just find a decent hotel when we got there. They were all either booked solid, or $700 a night. We wound up staying in some gross, smelly, Days Inn type place about 30 minutes away from the parks. I'll never try that again.

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9. Expensive Mistake, Generous Stranger

I was on a two month Europe trip. 6 days in, I headed to Paris. I walked maybe 10 minutes from the train station and spotted an ATM there on the main street. I needed Euros. So I got my card out, inserted it, punched in my pin, and then it asked me some question in French. I stared at the screen for a second, not sure what to do.

Suddenly a French man showed up, pointed at the screen and said some words I didn't understand. Then reacheed in with his right hand and pressed a button on the machine while his left hand held a newspaper, blocking my view. I heard a beep and he said, "You no validate." It was back to the screen I started at.

I asked furiously where my card was. He pointed and just said, "Machine. You no validate." I demanded my card but he insisted he didn't have it. Then he quickly walked off. I hit a couple buttons on the ATM and by this time the guy was running and jumping into a waiting car.

I ran half a block to a hotel and informed the front desk lady that I'd been robbed. At this point my card was gone and I never got my withdrawal. I foolishly called the police first, then my bank. I found out the man had seen my pin and already withdrew 500 Euros before the card was locked.

After a walk and over an hour at the police station, it was almost midnight. I had no Euros, and I was about 2 miles from my hostel. I asked the police for walking directions with hopes they might take pity on a stupid American. No luck.

Behind me at the police station was a family -- a mom, dad, and their kid about ten years old. They were from Saudi Arabia, and the wife's purse had been stolen. They were very well dressed and his English was nearly prefect. As the police were confirming my waking directions, the father interrupted. "Here, take this and catch a train." He was trying to give me money. I thanked him, but explained I had a credit card that should work as well. But he wouldn't let up.

I finally accepted and the police then started writing down which trains I needed. I thanked the guy again, and wished his family a good trip. Only when I had left the station did I realize this man gave me a 100 Euro bill. I'm still shocked till this day. So my plastic and cash got me through 3 more cities, but barely.

An expensive mistake, but a generous guardian angel.

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8. Glue It To Your Hand

My best mate did this one, I still giggle when I think of it. We arrive at airport to check in for flight. She forgot her passport. Classic. She had to rebook the next flight and hope that my dad could drive out her passport to us (she was living with me at the time). He couldn’t find the passport and she had to rebook again for the next day so she could go search. They never found the passport. The trip cost her $2,000 and she never went on it. I also did my first accidental solo travel which turned out awesome.

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7. All Or Nothing

Forgot my passport at the hotel so I missed my flight. Took a train to Paris instead because it was cheaper than rebooking a flight.

Got to Paris airport at the end of my stay to fly home and it turns out Delta has cancelled the second leg when I missed the first leg.

Had to buy a new $900 one way ticket home.

This was because my original tickets were booked as a round trip from Belgium to Paris and back to the USA.

Lesson for those who don't know: If you miss or skip any leg of your flight itinerary, your whole ticket will be cancelled. For example, even if you miss the last leg of your inbound flight, the return flight in two week will be cancelled.

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6. Technically

Ran up a $250 roaming charge on my last day in Switzerland... or should I say, ran up a $250 roaming charge with my Swiss cell phone carrier while at the Swiss airport... which is technically in France.

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5. Always Insist On A Menu

Went out to lunch with a group of friends in Athens, Greece. The place was packed with tourists, and seemed pretty decent, but mostly we went there because it was nearby and we wanted to eat quickly before doing some sightseeing.

The waiter listed off the food rather than giving a menu (red flag). We ordered stuff that should be cheap, like souvlaki and water, no drinks. We decide to keep it as one bill and just pool our money.

When we got the bill and it was $250 for 5 people. If this was Seattle, that would be normal, but this was Athens. Not only did they overcharge for food, but the water bottles that each one of us got cost about $10 each (and I know for a fact you can get 6 packs of those huge water bottles for like 10¢ at the grocery store).

Luckily me and one of my friends were carrying large bills with us, so the two of us covered the meals and were paid back by our friends later. I’m still angry about it.

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4. Rotten In The State Of Denmark

Taxis from the airport in Copenhagen are scams. They charged 835 Krone, which was $170.00. We told the concierge at the hotel, and they were angry. The night before we left, the hotelier warned us to make sure we agreed on the fixed rate before we got into the cab. The next morning, a different desk clerk gave the taxi driver a stern talking-to. As we travelled, we noticed the meter was running, instead of the fixed rate agreed upon. We told him to stop the car and let us out. He then phoned somebody, pretended to argue, and then agreed to the fixed rate.

Copenhagen is wonderful, but don't take taxis.

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3. Never Go With Strange Women

Got taken by a clip joint in Budapest.

I've written about this before, so let me summarize:

Two women greet my buddy and me. I don't like it but he insists we go with them.

They take us to a club. Now I really don't like the scene. My buddy overrules me, tells me not to worry.

The bill for 12 drinks appears: $700. We've clearly been scammed.

I am forced to an ATM to withdraw the cash. I pay.

My buddy afterward argues we should split the cost and he gives me $350. I'm still out at $350 and very angry at him.

Men: Don't ever go somewhere with a strange woman. Or man for that matter. If a stranger insists on joining you for a drink or a coffee or a tea ceremony, then YOU pick the destination. If they balk and insist on going to their choice location, then you know they are trying to cheat you. Walk away.

This is the most common scam in Eastern Europe. A general rule of thumb for American and British men traveling in this part of the world, especially those who don't have much experience dating abroad: pretty local women are never just going to approach you, no matter how cool or good looking you think you are. The vast majority of the time, the ones who do are girls who are looking to make money off you.

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2. A Very Expensive Date

I once bought 2 cups of tea and a slice of watermelon in Beijing that cost me $250. Allow me to elaborate…

I was on a 4-day business trip in Beijing. At that time, I had never been to China, although I had traveled to a number of different countries in the past and considered myself fairly ‘aware’ as newbies go.

Day one, I arrived and caught a cab to the hotel. I had no cash, planned to only use my credit card while I was away and didn’t even take the few seconds to even glance at the exchange rate before I left. Needless to say, I had no idea about the currency, so didn’t know what things were priced at.

The ONLY thing I did organize before I went was my bicycle hire, as I planned to bike around the city in my downtime. So I checked in to the hotel and then headed straight out with a print out of Google Maps with an arrow pointing to where the bike hire place was.

I wandered down a busy street staring blankly at the buildings trying to find my way around when, lo and behold, a cute girl approached me and offered to help. She was studying English and would love to practice with me. I was flattered she had chosen me to help her expand her knowledge of the English language.

She pointed me to the bike hire place (my booking was not until the following day) then offered to go for a drink to chat and learn more about Australia, which she would love to visit one day.

As I type this I’m still laughing at myself.

Lots of idle chit-chat later (her English was surprisingly excellent, not a fact I noticed at the time) we found ourselves upstairs at a small tea house. Upon reflection, I remembered that the only customers other than myself and my new tour guide were 4 older gentlemen playing cards.

So we chatted and had a cup of tea each. Green tea if I recall. The waitress offers some watermelon, to which I oblige, and after about 30 minutes, I of course offer to pay. The waitress presents the bill which totals about 1200RMB. Of course I have no idea how much that is, so I hand over my card and sign the receipt, never once suspecting foul play.

We cordially parted and I sincerely thanked her for her wonderful hospitality. I trotted down the stairs out into the busy street and headed in the direction of my hotel, feeling quite charmed by this lovely encounter.

That’s when I walked past a men’s clothing store with a very smart suit hanging in the window. The price tag was 800RMB. I continued back to my hotel.

Slowly… very slowly… the penny dropped. “800RMB for a suit. Wow, that’s cheap!”

Even more slowly… “That doesn’t seem right, surely that suit is not a couple of dollars.”

I got back to the hotel and asked my colleague what the currency conversion was. About 5 to 1. Slowly the math computed… I just paid about $250 for tea!

I quickly called my bank and informed them that I suspected my card had been overcharged and I disputed the transaction. They informed that it was common and I would most likely get the money back.

I didn’t.

3 months later I received a letter from my bank, containing the exact receipt with my signature right there below the 1200RMB total.

To this day I still marvel at the number of man hours the bank invested in tracking down proof of my ineptitude. Surely it totalled exponentially more than the $250 it would have cost to just refund me.

Ben Petro

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1. Unfortunately, The Philippines Are Known For This

When I flew into Kalibo in the Philippines, I had about $600 in cash in my bags. Airport security took me away from my bags for “extra checks”. Once I got to the side, the guy just wanted to chat about MTV and Miami for 10 minutes. When I got my bags back, all of my cash was gone.

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