10 Las Vegas Mistakes I Keep Making Even Though I Know Better

I’ve been to Las Vegas enough times that I really shouldn’t be making rookie mistakes anymore.

I know the Strip is farther than it looks. I know hotel markets charge ridiculous prices for water. I know I’m probably not going to wear half the clothes I pack. I know staying out until stupid o’clock before an early flight home is a terrible idea.

None of this is new information to me.

And yet I keep doing all of it.

These aren’t necessarily the biggest mistakes you can make in Las Vegas. I’m not talking about forgetting to set a gambling budget or booking a hotel without checking the resort fee. These are the stupid little mistakes I personally keep making trip after trip even though I have absolutely no excuse anymore.

At this point, they’re basically traditions.

Here are 10 Las Vegas mistakes I keep making even though I know better.

1. I Pack Like I’m Going to Dress Fancy

Every time I pack for Las Vegas, I apparently imagine a completely different version of myself taking the trip.

This guy dresses nice.

He has outfits planned for dinner. He brings different shoes. He apparently believes there will be occasions where a band T-shirt just isn’t going to cut it.

So I pack accordingly.

Then I get to Vegas and wear band T-shirts, cargo shorts and Vans every single day.

That’s it.

That’s my Vegas uniform.

I’ll look into my suitcase and see all the clothes I brought and think, “Maybe tonight I’ll actually wear that.”

Nope.

Band T-shirt. Cargo shorts. Vans.

Tomorrow?

Different band T-shirt. Same basic idea.

I’ve done this enough times that you’d think I would finally accept who I am. Instead, every Vegas trip begins with me wasting suitcase space on clothes belonging to an imaginary, slightly classier version of myself.

What I should do instead: Pack for the person who is actually going to Vegas, not the person I apparently think I’m going to become when the plane lands.

I’m probably never going to learn this one.

I’ll spend time figuring out things like how to use mobile check-in and the $20 trick to improve my Vegas hotel stay, then turn around and make mistakes that could’ve been avoided with about five minutes of common sense.

2. I Still Put Money on Red Because of Entourage

This might be the dumbest Vegas tradition I have because it basically came from television.

Years ago, I saw them make a big roulette bet on Entourage. I don’t even remember if they bet red or black anymore. All I know is somewhere along the way, my version became red.

So now I have this habit of walking up to a roulette table and putting money on red.

Usually it’s $100.

Sometimes it’s $50 when the responsible part of my brain briefly takes control.

There’s no strategy behind this.

I’m a blackjack guy. I spend all this time learning basic strategy, practicing hands and trying to make mathematically correct decisions.

Then I get to Vegas and basically go:

“Yeah, but what if red?”

The worst part is I’ve won enough times doing it that I’ll probably never stop. If I had lost the first six times, maybe the tradition would’ve died naturally.

Instead, I’d honestly estimate I’m somewhere around 50/50.

And yes, I understand that’s not how roulette works long term. Don’t send me an email explaining probability.

What I should do instead: Nothing. There is absolutely no good reason for me to keep doing this.

What I’m actually going to do: Put money on red again next trip.

3. I Still Think Everything in Las Vegas Is Walkable

Las Vegas has some kind of optical illusion where every building looks like it’s right there.

You can see the casino.

How far could it possibly be?

Pretty damn far, apparently.

I’ve walked from Downtown Las Vegas all the way to Treasure Island.

I’ve walked from the Strat to the Flamingo.

I’ve walked from Mandalay Bay to Bellagio.

And somehow, despite personally gathering all of this evidence, I still occasionally look down the Strip and think:

“We can walk that.”

The problem is you don’t just walk from one casino to another.

You walk through the casino. Then through a shopping area. Then across a pedestrian bridge. Then around construction. Then up an escalator. Then through another casino. Then down another escalator.

Forty minutes later, you somehow feel like you’re approximately 14 feet closer to your destination.

Vegas miles aren’t normal miles.

The Strip is especially good at making a destination look close enough that ordering an Uber feels ridiculous.

Then 45 minutes later you’re sweating, your feet hurt and nobody is talking anymore.

What I should do instead: Check the actual distance before deciding to walk somewhere instead of judging it by whether I can see the building.

Of all the lessons on this list, this is probably the one Las Vegas has tried hardest to teach me.

I remain a terrible student.

4. I Eat Way Too Much Overpriced Pizza

I don’t go to Vegas planning to eat pizza all week.

It just happens.

The problem is pizza is everywhere, it’s fast, and there’s almost always some pizza place closer than whatever restaurant I originally thought I was going to visit.

And once I’m gambling, convenience starts winning every argument.

Hungry but don’t want to stop gambling for long?

Pizza.

Need a snack?

Pizza.

Actual dinner?

Apparently also pizza.

I’m not even necessarily seeking out the best pizza in Las Vegas. Half the time my restaurant selection process is basically:

Which pizza is currently open and closest to me?

That’s how I end up paying Vegas prices for a couple slices of completely average pizza that I probably wouldn’t even think about buying at home.

Then I’ll do it again the next day.

The annoying part is Las Vegas has an insane number of restaurants I genuinely want to try. Before every trip I’ll save places and tell myself we’re finally going there.

Then I’m standing in a casino at 11:30 at night eating another slice of pizza.

What I should do instead: Actually plan at least one real meal each day and stop letting proximity make every food decision for me.

Will that happen?

There’s probably a slice of pizza somewhere between my hotel room and the restaurant, so I’m not making any promises.

5. I Drink Way Too Much When I’m Having Fun at a Blackjack Table

This one always sneaks up on me.

I’m sitting at a blackjack table. The table is fun. I’m talking to the dealer and the other players. Maybe I’m winning.

Then the cocktail waitress comes around.

Sure, I’ll take another one.

Twenty minutes later she comes back.

Sure.

Then again.

Sure.

Eventually I’ve completely lost track of how many drinks I’ve had because I’m not sitting at a bar ordering them one after another. They just keep appearing while I’m doing something else.

And when I’m having a really good time at a blackjack table, I’m probably not getting up anytime soon.

That’s when those “free drinks” start catching up with me.

They obviously aren’t really free. I’m sitting there risking money every hand while drinking them. And after enough of those drinks, I’m probably not making better gambling decisions.

The irony is I’ve spent plenty of time learning and practicing perfect blackjack strategy, only to occasionally sabotage all that studying by having a few too many drinks while I’m actually sitting at the table.

I’m also definitely not getting quieter.

There’s a point during some blackjack sessions where I suddenly realize I’m way more drunk than I thought I was.

Usually several drinks after the point where I probably should’ve realized it.

What I should do instead: Mix in some water and occasionally tell the cocktail waitress no.

That sounds incredibly reasonable while I’m sitting here writing this.

We’ll see how reasonable I am three hours into a good blackjack table.

6. I Keep Playing Huff & Even More Puff Even Though I Know Better

I have a toxic relationship with Huff & Even More Puff.

That machine does not like me.

I know it doesn’t like me.

I’m not even sure I’ve ever had a legitimately good session playing it.

Yet somehow I keep going back.

Usually it happens after I’ve already been gambling for a while. Other games aren’t treating me particularly well, and somehow my brain decides the solution is to go play the slot machine that treats me even worse.

I’m always waiting for the bonus.

Surely I’m due.

I’ve played this thing enough times that the bonus has to be coming.

That’s obviously not how slot machines work, but apparently nobody has explained that to the version of me sitting in front of Huff & Even More Puff.

I’ll start with a smaller bet.

Then maybe increase it.

Then sit there watching my money disappear while thinking the next few spins are going to turn everything around.

They usually don’t.

Eventually I walk away telling myself I’m done with that game.

Never again.

Then the next trip comes.

“Oh look, Huff & Even More Puff.”

And the cycle begins again.

What I should do instead: Walk directly past it.

What I’ll probably do instead: Sit down because this time feels different.

7. I Stay Out Way Too Late Before an Early Flight Home

I do this almost every trip, and it makes absolutely no sense.

I know when my flight leaves.

I know what time I need to wake up.

I know I have to pack, check out, get to the airport, deal with security and eventually sit on an airplane wishing I were unconscious.

So naturally, the night before all of this, I stay out ridiculously late.

There’s something about the final night in Vegas that makes going to bed feel like admitting the trip is over.

One more casino.

One more blackjack session.

One more drink.

I’ll go upstairs in a minute.

Then “in a minute” becomes another hour.

Eventually I get back to the room, look at the clock and immediately start doing the math.

“If I fall asleep right now, I can get…”

That’s never a sentence that ends with a good number.

Then the alarm goes off approximately seven minutes later and I hate every decision I’ve made since dinner.

What I should do instead: Treat the final night differently and actually go to bed at a reasonable time.

But apparently I’d rather be exhausted in the airport than sacrifice two hours of Vegas.

8. I Pay Ridiculous Hotel-Market Prices for Water and Snacks

This one might bother me the most because I am fully aware I’m getting ripped off while I’m doing it.

I’ll walk miles in Las Vegas because I don’t feel like paying for an Uber.

But put me in my hotel at night when I’m thirsty?

Suddenly walking somewhere to buy reasonably priced water seems impossible.

So I go into the hotel market.

I grab a bottle of water.

I look at the price.

I get annoyed.

And then I buy it anyway.

Same thing with snacks.

I know there are CVS stores, Walgreens, ABC Stores and other places where I can stock up without paying casino-market prices.

I’ve been to Vegas enough times to know exactly how this works.

Even when I’m staying somewhere I know well, like MGM Grand, convenience eventually wins and I end up paying casino prices for something I could’ve bought somewhere else for a fraction of the price.

I just don’t prepare.

Then it’s late, I’m thirsty, I’m tired and convenience wins.

Again.

There’s something especially painful about paying an absurd amount of money for a bottle of water because there isn’t even a chance of hitting a bonus round.

What I should do instead: Buy several bottles of water and some snacks at the beginning of the trip and keep them in the room.

This is probably the easiest problem on this entire list to solve.

Which means there’s a very good chance I’ll still screw it up.

9. I Forget How Much More Vegas Costs When You Bring the Kids

I want to be very clear about this one:

Bringing my kids to Las Vegas wasn’t the mistake.

We’ve had a great time doing Vegas as a family, and I’d absolutely bring them again.

The mistake was thinking about the cost like it was going to be one of my normal Vegas trips.

Vegas math changes dramatically when you bring kids.

When it’s just me and Nikki, grabbing something to eat means paying for two people.

Bring the kids and suddenly every meal costs considerably more.

Then there are drinks.

Snacks.

Attractions.

Arcades.

Tickets.

And all the random stuff kids see along the way and want to do.

It adds up ridiculously fast.

We stayed at Excalibur on one of our family trips, and it was actually a great hotel for what we were doing. There was plenty around to keep everybody entertained, and we made some great memories on that trip.

But keeping everybody entertained costs money.

A lot more money than two adults wandering around casinos.

The funny thing is some of my favorite Vegas memories have come from trips where we brought the kids. So I definitely wouldn’t change that part.

I’d just budget completely differently next time.

What I should do instead: Stop calculating a family Vegas budget like it’s my regular Vegas budget with a couple extra plane tickets.

Kids don’t gamble.

Unfortunately, they still somehow cost more than I do.

10. I Make All These Vegas Plans and Then Ignore Them

Before every Las Vegas trip, I’m incredibly ambitious.

This is going to be the trip where I finally go to Hoover Dam.

I’ve probably said that 20 times.

I have still never been to Hoover Dam.

I’m going to visit Green Valley Ranch.

Still haven’t.

I’m definitely checking out Durango this time.

Nope.

I’ll tell myself I’m going to visit a museum I’ve never seen before.

Then somehow I end up back at the Punk Rock Museum.

Again.

At this point, I don’t even know why I continue pretending I’m an itinerary person.

I like making the plans. I like looking up restaurants, casinos and things I haven’t done before. And when I’m sitting at home planning the trip, I genuinely intend to do all of it.

Then I get to Vegas.

And Vegas starts happening.

Maybe I’m having fun at a blackjack table and don’t want to leave.

Maybe Nikki and I start walking somewhere and completely change our plans.

Then again, Nikki and I have never exactly been known for doing Vegas the conventional way. We did get married in Las Vegas after all, so maybe expecting us to follow a carefully planned itinerary was unrealistic from the beginning.

Maybe we have a few drinks.

Maybe something completely unplanned catches our attention.

Suddenly the thing that was absolutely happening Tuesday afternoon gets moved to Wednesday.

Then Thursday.

Then “next trip.”

That’s basically where Hoover Dam has lived for years.

And honestly, I’ve started realizing that might not be such a terrible thing.

Some of my favorite Vegas stories weren’t on an itinerary.

They happened because we changed our minds, started walking somewhere, sat down at a blackjack table or did something completely different from what we planned.

What I should do instead: Stop building a Vegas trip around a giant checklist. Pick one or two things I genuinely want to accomplish and let everything else happen naturally.

Although at this point I should probably just stop pretending I’m going to Hoover Dam.

Apparently Knowing Better Doesn’t Help

That’s probably the funniest part about all 10 of these mistakes.

None of them are mysteries anymore.

I know I’m going to wear band T-shirts, cargo shorts and Vans, yet I’ll probably pack clothes I never touch.

I know Las Vegas distances are ridiculous, yet I’ll look at a casino two miles away and decide it doesn’t look that far.

I know Huff & Even More Puff hates me.

I know I should buy water somewhere cheap.

I know I should sleep before an early flight.

And I know Hoover Dam isn’t going to magically drive itself onto the Strip so I can finally see it.

I’m literally writing an entire article documenting all of this, so I can’t even claim ignorance anymore.

But when I’m back in Vegas, there’s about a 100% chance I’ll have a suitcase full of clothes I won’t wear, money sitting on red because of a TV show I watched years ago, and an overpriced bottle of water in my hand.

At least now when I do it again, I can call it content.

Frequently Asked Questions About Las Vegas Mistakes

What are some common Las Vegas mistakes to avoid?

Some of the easiest Las Vegas mistakes to avoid are underestimating walking distances, paying hotel-market prices for water and snacks, overpacking your schedule, drinking too much while gambling, and staying out too late before an early flight. I’ve made all of these enough times that I should definitely know better by now.

Is walking the Las Vegas Strip harder than it looks?

Absolutely. Casinos that look close together can take much longer to reach than you expect because of pedestrian bridges, massive casino properties, crowds, construction and indirect walking routes. I’ve walked from Mandalay Bay to Bellagio and from the Strat to Flamingo, and somehow I still underestimate Vegas distances.

How can I avoid overspending on food and drinks in Las Vegas?

Buying water and snacks away from hotel markets can save money, and having at least a loose plan for meals helps prevent convenience from making every decision. Otherwise, you might end up like me—paying too much for whatever pizza happens to be closest and buying an overpriced bottle of water because you don’t feel like walking anywhere.

Is Las Vegas more expensive when traveling with kids?

In my experience, yes. Bringing my kids to Las Vegas was absolutely worth it, but meals, snacks, drinks, attractions, arcades and entertainment add up quickly. I’d budget much more for a family Vegas trip than I would for a trip with just two adults.