7 Travel Rules I Used To Swear By… Until They Nearly Ruined My Trips!

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I Thought These 7 Travel Rules Were Foolproof, Until They Almost Wrecked Everything!

From “always book in advance” to “avoid street food”… here’s why some of the most common travel advice is dead wrong.I thought I had travel figured out.

I followed all the so-called expert rules… until they left me stranded in a dark alley in Tbilisi, locked out of a “boutique” guesthouse with 2% battery and a judgmental stray dog.

It wasn’t my first failure. I avoided street food in Bangkok, only to get food poisoning from a “fancy” restaurant in Spain.

Did some sightseeing in Kyiv’s “safe” tourist zone downtown and almost got scammed.

One guy pretended to find a wallet and offered to split the cash, claiming it was my “lucky day.”

Moments later, a fake cop showed up, searching for a lost wallet.

That was the infamous Dropped Wallet Scam!

Turns out, some travel rules will save you… others will leave you broke, sick, or completely screwed.

Here are seven “foolproof” travel rules I swore by that turned out to be completely, utterly, hilariously wrong.

And what actually works instead.

1. Always Book Everything in Advance… Or Risk Paying More

Why I Believed It:
I was convinced that booking everything ahead of time was the only way to “win” at travel.

After all, every travel guide, blog, and Reddit “expert” insisted that without booking flights, hotels, and activities in advance, you’d pay triple.

Otherwise, you’d end up on a park bench under a tree with some very judgmental pigeons taking aim, if you know what I mean… lol.

How It Backfired:
Fast forward to a cold November night in Ukraine. I arrived at my “confirmed” Airbnb in Odesa, only to find it didn’t exist.

Not “the host ghosted me” kind of didn’t exist… like “there was literally no building at the address” didn’t exist.

I stood there, rereading my confirmation email in disbelief, as my taxi driver nodded knowingly and said, “Ah, yes… scam.”

Apparently, I wasn’t the first victim of this disappearing act.

The host had double-booked, never updated the listing, and now I was wandering around Odesa with all my bags, wondering if my backup plan was going to involve sleeping at a 24-hour café next to the train station.

The Better Strategy:
Book some essentials, your first night’s accommodation, peak-season flights… but leave room for flexibility with hotels, activities, and local transport.

Some of the best stays I’ve had were last-minute deals I found while already in the country.

And let’s be honest, sometimes, you’ll fall in love with a city and want to stay longer (or, in the case of that non-existent Airbnb, leave immediately!).

2. Avoid Street Food… It’s Unsafe and Will Make You Sick

Why I Believed It:
For years, I avoided street food like it was personally out to get me.

I had been warned by every well-meaning traveler about the “mysterious” stomach issues that lurked in the shadows of every taco stand and noodle cart.

How It Backfired:
So, there I was in Bankgok, being a responsible adult, dining in a “proper” restaurant… where I got “the worst food poisoning of my life.

While my friends happily devoured popular Pad Thais and fresh Somtum Papaya salads with no ill effects, I spent the next 48 hours in a fever dream, making regrettable life choices involving electrolyte drinks and Google searches I wish I could “unsee”.

Meanwhile, in Mexico, I refused to eat fresh shrimp tacos from a busy street vendor in Cozumel, only to order the exact same dish at a fancy rooftop hotel restaurant in Cancun at four times the price and half the flavor.

The Better Strategy:
Street food isn’t the enemy… bad food handling is.

  1. Look for busy vendors where locals eat (high turnover = fresh food).
  2. Avoid pre-cut fruit, lukewarm buffets, and empty vendors with food that’s been sitting out in the sun all day.

If an old lady is frying something in front of you and there’s a line of people waiting?

That’s the safest meal you’re going to get!

3. Stick to Tourist Areas for Safety

Why I Believed It:
Tourist zones seemed like the safest bet, familiar, well-lit, and heavily policed.

Plus, they were where everyone went, so surely they were the best areas to stay in… right?

How It Backfired:
Tourist areas are “the” places where you’re most likely to get scammed, overcharged, or stuck eating bad pizza while paying triple the local price.

Case in point: Madrid. I was charged “€18“ for a sad, microwaved plate of paella in Plaza Mayor while the “same dish” was being served one street over for “€7… and actually made fresh”.

Meanwhile, my former teaching colleague in France once paid an absurd amount for a “traditional” Parisian meal in Montmartre, only to find out later that the “chef was actually from New York”.

The Better Strategy:
Step outside the tourist bubble. “Research where locals actually go”.

If a menu has “pictures” of food and six different translations, run!

And trust me, venturing even “one or two streets” away from the tourist traps can make a world of difference in price and authenticity.

4. Travel Light… One Carry-On Is All You Need

Why I Believed It:
Minimalist travel is everywhere. I saw seasoned backpackers stuffing a week’s worth of clothes into a tiny bag and thought, If they can do it, so can I!

How It Backfired:
France. “Winter”. I packed for “efficient travel,” which apparently meant two sweaters and some optimism.

By the second week, I was layering all my clothes at once, looking like an overstuffed burrito just to survive.

Sure, I “traveled light.” I also froze my ass off and spent more money buying clothes I could have just packed in the first place.

The Better Strategy:
Packing light is great “until it isn’t”. If you’re going to a single climate for a short period, a carry-on works.

But if the weather varies, or you’ll be moving around a lot, don’t be afraid to check a bag.

Overpacking is bad… but so is under-packing yourself into a survivalist challenge.

5. Convert Money Before You Leave… To Avoid ATM Fees

Why I Believed It:
Everyone warns about high foreign ATM fees, so I assumed it was better to get all my cash exchanged before leaving home.

How It Backfired:
I exchanged “$500” back in 1998 before heading on my first trip to Spain for the Camino De Santiago, only to immediately regret it when I saw the exchange rate.

After losing 10% to bad conversion fees, I still had to “withdraw more” later.

Plus, carrying that much cash felt like I had a neon sign above my head that said ”MUG ME” in some questionable areas of Barcelona.

The Better Strategy:
Use a “good travel-friendly debit card” (like Schwab (for Americans), Wise or Revolut) that avoids high fees.

Withdraw “small amounts locally at reputable ATMs” for a better rate.

And “never” exchange money at the airport unless you enjoy getting ripped off.

6. Always Follow the “Cheapest” Option

Why I Believed It:
Saving money means smarter travel, right?

How It Backfired:
Ever booked a $20 Ryanair flight that “actually” cost you $120 after bag fees, train tickets to a “secondary” airport, and a layover that made you question your life choices? Because I have.

Or how about that “super cheap” hostel in Spain, where I saved “$5 a night” and gained “a mysterious rash and a roommate who may or may not have been an unregistered pet squirrel?”

The Better Strategy:
Calculate “true costs”, time, comfort, and hidden fees.

Sometimes, paying slightly more saves you money and sanity in the long run.

7. Plan Every Day in Advance to Maximize Your Trip

Why I Believed It:
Travel FOMO made me feel like “if I wasn’t busy every second, I was doing it wrong.”

And it was exhausting!

How It Backfired:
I scheduled every minute in Paris tours, the Louvre, even restaurant reservations.

Meanwhile, my friend had “zero plans” and somehow stumbled into a local festival, free drinks, and an invite to a private rooftop party.

I spent €50 on tickets to an “exclusive” show at the world famous “Moulin Rouge”.

He watched a spontaneous street performance for free.

The Better Strategy:
Leave “at least one unplanned day per destination”.

Say yes to unexpected opportunities instead of following a rigid checklist.

Some of the best experiences aren’t in your itinerary.

Travel Isn’t One-Size-Fits-All

The best travel experiences often come from breaking the rules. What works for one trip might be a disaster for another.

Stay flexible, adapt, and don’t be afraid to ignore the “experts” (yes, even me).

So, what’s the worst travel advice you’ve ever followed?

I need to know I’m not alone in my terrible decisions.