How to Avoid these Italy Travel Mistakes and Have a Spectacular Italian Vacation

Okay, so if you follow me in the cyber world at all (and I pray to God that you do because my follower is getting pretty lonely.

Yeah, we’re talking Into the Wild lonely), then you probably saw that I traded my New York City subway metro card for an Italy travel map as I barreled my way through one day in Milan, Rome, and Naples during Christmas this year (Woot Woot. Sorry but I had to abandon New York City for the holidays).

Now obviously, this trip would not be “Girl with the Passport level” awesome without some epic travel blunders that will make you laugh, convulse with laughter, and then laugh some more.

Seriously, don’t read this in a library because I cannot be held responsible for your reaction to the fact that I ended up staying at an AirBnB with a stripper after my Pakistani prince saved me from the not so mean streets of Naples (yes, this is all true.

I wish I could just gush about some awesome food tour of Napoli).

But besides a good laugh at the sheer insanity of my life, let’s be real, you’re here to (insert valley girl “like” here) actually learn something.

I mean, as funny as it is to bunk with a stripper and to have some random Pakistani man coming in and out of your Airbnb, I doubt that’s really how you want to spend your very Italian vacation.

You also don’t want to waste your hard-earned cash o anything less than the absolute best Italian gifts for Italy lovers. 

Instead, you probably have visions of Under the Tuscan Sun, Eat Pray Love, or Roman Holiday sashaying through your subconscious.

You know, super romantic ideas of you hanging out in some of the best Tuscany hot springs and thermal baths. 

And I get it because I totally wanted to grab a gelato and hop on the back of some hot Italian guy’s Vespa; a guy that was not forty and still living with his mom (but beggars take what they can get).

You also might see yourself frolicking through a picturesque vineyard, amidst an exquisite range of Italian Mountains that I don’t know the name of because I SUCK at geography.

But nowhere in this Italy solo travel fantasy do you see the words “Euro Trip” or “National Lampoon’s Italian Vacation” (See how I did that and just appealed to a wider age demographic? Tricky tricky) anywhere.

And let’s be real, you want to keep it that way, which is why should check out some of these movies to watch before traveling to Italy.

So enough of this intro fluff BS because we are all social media whores who have the attention span of a Tsetse fly.

So before I lose you and you roll out like Flavor flav at clock time, let’s carry on with some anti-cute, Italy travel mistakes, and some interesting facts about Itay, that you might want to avoid during your 2 week Europe itinerary.

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If you’re booking a trip right now then I IMPLORE you to get travel insurance – even if it’s not from me.

After all, this past year has been a wild ride and I don’t want you to lose money because government regulations have changed. 

Truth be told though, I’ve never traveled without travel insurance and don’t think you should either – especially since I think we’ve all had plans drastically change because of the pandemic. 

Therefore, find an insurance agency that covers travel changes related to COVID-19, like my two all-time faves World Nomads and Safety Wing. You can also read more about which policy is right for you in my full review here.

1. Not Buying EVERYTHING in Advance (unless you’re doing Italy slow travel and have all the time in the world)!

Aww, you’re doing Italy solo travel and thought you were gonna just walk into the Vatican Museum and see all their amazing art (you can if you visit the Vatican at night)?

That’s so cute. Yeah no. A more likely scenario is that you’ll be herded through a series of Museum corridors as you frantically try and sneak a peak at the Sistine Chapel before the museum closes.

And no, I am not on the rag, emotionally unbalanced, and totally exaggerating.

There is one and only one route to the Sistine Chapel and not surprisingly, people will practically trample you just to see this artistic marvel. So yes, you really do feel like you’re in City Slickers and someone is about to yell, “Raw High”.

But even if you’re not going to some super famous attraction, book a ticket in advance anyway. Seriously, just do it.

Yeah, it costs a little more but I promise, you won’t regret it. I mean in Italy, waiting in line feels like a sport and national pass time, all rolled into one; translation, you wait in line for anything and everything.

No joke, I waited in line for fruit, FRUIT, from the grocery store. And this wasn’t some rare dragon and passion fruit hybrid that is grown in the deep reaches of space, it was an apple.

An apple! And sure, it was fresh, crispy and delicious, but it’s not like I saw a burning bush or gaped in awe as Beavis and Butthead crawled through the TV and jumped out right in front of me (and lit a fart on fire).

So be prepared (Lion Kind anyone? Scar is so misunderstood. Kidding. I was a Pumba fan), and book everything in advance, especially if you’re planning quick trips, like a short, 2 days in Venice itinerary or a fantastic, 2 days in Bologna. Also book a room at one of the best boutique hotels in Milan in advance too.

Because let’s be real, no one wants to spend their vacation waiting in line, especially when you’re standing behind a family of five who has three screaming kids that whoops, drop their ice cream all over you (Not from personal experience or anything.

And those pants were so two weeks ago so obviously I didn’t want them anymore).

***If you only book ONE ticket in advance, then it should be the Skip the Line Vatican and Sistine Chapel By Night Tour. Not only will you get to skip the horrendous ticket line, but you’ll also get to enjoy the Vatican when it is peaceful and is closed to the public. 

***If you want to be extra prepared, also get the skip the line ticket for the Coliseum, Roman Forum, and Palatine Hill, as well as the Borghese Gallery Reserved Entrance Ticket (This museum is gorgeous and DOES sell out). 

2. Failing to Watch your step.

Hmm, how do I put this delicately because I love Italy and cannot wait to go back but er, um, I feel like fixing things is not really a top priority in Italy?

Maybe they just love ancient history and want streets, sidewalks, and staircases to turn into antiques?

Well, whatever the case, another one of my Italy travel tips is to watch where you’re stepping, lest you end up in a pothole and twist your ankle.

And unlike in the United States, Italians don’t do frivolous lawsuits so if you get hurt, you better have some damn good travel insurance because no one here is suing McDonald’s because they are fat (actually lawsuit in the US).

Actually, now that I’m sort of on the subject of safety, watch out for rogue cars and Vespas because pedestrians don’t really get the right of way.

Kind of like in New York, whoever is bigger and badder and has more horsepower gets to cross the road first. Stop signs and traffic lights are also kind of optional.

Therefore, wait your turn because you don’t want to end up in a body cast (You don’t want to increase your Italy travel costs like THAT and sadly, not a super Instagram worthy moment because most people don’t look banging’ in a body cast).

3. Going to a Restaurant before 7:30 pm

Oh you wanted to be like the Golden Girls and have the Early Bird special? Not gonna happen, unless you enjoy overpriced tourist traps with mediocre at best food.

Yeah, Italians generally eat dinner late so if a place is open early for dinner, it’s a tourist trap and you should run away. Just pretend that the T-Rex from Jurassic Park is chasing you.

Nobody wants to be THAT guy who was eaten on the toilet, not a good look.

But look before you cross the street and watch out for the Grand Canyon, I mean potholes (kidding, it’s not that bad).

So try and hold out because the wait is worth it. The best and most authentic restaurants usually don’t open their doors until 7:30 pm.

Come to think of it, some of the best places I went to had a line out the door, no name, and no set menu because the chefs went to the market that morning and just prepared all the best ingredients they could buy.

Also avoid places that have a menu that is built for the United Nations (if you are worried about finding a good place to eat, you can always head to Italy’s famous food region and try some of the best wine tours in Florence for a more authentic experience.

You know, the restaurants that print the menu in Swahili as well as English, Spanish, Brail, and Sign Language. Yeah, they have them in places like Venice and that is not where you want to go when in Venice at night.

Best to walk right past those train wreck restaurants and, as painful as it is, flock towards the insanely long line of Italian people (hey, sometimes you gotta follow the locals to the holy grail of all pizza. Yes, Italy food travel at its finest). Yeah, I did this after my Naples to Amalfi Coast tour and it was worth it.

4. Relying on Free Wifi

What, you can’t read this because Italy is largely devoid of free public wifi? Yeah, I hate to say it but this is absolutely TRUE! I found wifi in Italy to be pretty scarce, unless you are at an establishment that has its own wifi network.

So if you need to stay connected and get chronically lost like me, then make sure you have a Sim Card with data or purchase a mobile hotspot (like skyroam which is one of my many great Italy travel gifts) because if you don’t, you might go into Facebook status update withdrawal (it’s okay, I also stalk my former bullies on Facebook and make sure they are losing at life. We’re in it together).

5. Using a Map to Navigate

If you only listen to one thing I say, this should be it.

Make sure you have wifi with you at all times, otherwise you will get totally lost and spend half your vacation asking bewildered Italians for directions ( I did so with my puppy dog eyes of sorrow.

Yup, I got tons of pity directions. Actually this was mostly in Naples because all the streets looked the same). At least, that’s how it was for me but in fairness, I’m directionally challenged.

However, I don’t think it’s just me because not only do many of the streets look the same, many don’t have street signs (if they do then I need to see my eye doctor asap).

So um, good luck trying to find anything if you’re not from the area. That’s why I would have some sort of navigation device on hand because otherwise, you’ll emerge from this virtual labyrinth of Italian streets looking less like Cindy Crawford/George Clooney (You gorgeous lady or handsome man you.

See, I complimented you so now you HAVE to like my blog. Please love me? Okay, shaking off the neediness. Just don’t ghost me) and a lot more like the Crypt Keeper from Tales of the Crypt.

***If you don’t have access to wifi then I implore you to download a city guide on Triposo. This app is a trip planning app that works offline. While the app won’t give you turn by turn directions offline, it will show you where you are in relation to the attraction you are looking for.

Seriously, this little app has saved my ass more times than I can count, and as you know, my ass gets into an epic amount of trouble.

6. Thinking that you’ll just use the Subway to get Everywhere (this applies to Rome mostly).

Hahahahahaha. I was under this delusion and I was wrong, so very wrong. Okay, I better explain this one or the Italy travel forum will have my head on a silver platter.

Because I swear, I am not dissing Italy’s public transportation system. The public transportation in Italy is fine, it’s just that Italy is home to the remnants of the biggest empire in history; artifacts that are scattered throughout cities like Rome.

Therefore, major portions of cities, like Rome, have protected, historic ruins that you can’t just  blast your way through to create a new metro line for all the tourists doing the Rome Italy travel portion of their holiday.

That’s why yes, you can use the metro, but it just won’t  take you everywhere you need to go. So make sure you have a pair of good walking shoes, a bus schedule, and know where the nearest Taxi stand is because I can honestly say that I have never taken more taxis in my entire life.

***PS Italy has designated taxi stands so you don’t need to hail a cab off the street. Now you may be wondering why I don’t mention buses a whole lot. Well, I am not a huge fan because I never know when my stop is. So I get super anxious and spend the entire trip glued to the window, trying to decipher which stop is actually mine while the bus speeds by. So yeah, not my idea of a hopping good time.

7.  Sitting Down and Paying $3.00 (euros) for coffee.

First of all, Italians don’t drink coffee sitting down, they just don’t. You go to the espresso bar and order a cup of coffee standing up.

Why? Well, if you sit down then you pay a service charge and nobody wants to pay more for the same  cup of coffee.

Plus, it makes me feel a little better to know that Americans aren’t the only ones who drink their coffee on the go. Sorry, let’s veer away from my looming sense of American inadequacy.

So in a nutshell, this is why you should stand at the bar and order your Cappuccino, Macchiato, or whatever else you want, like a pseudo-real Italian.

Another great piece of Italy travel advice is that if you order a coffee, they will give you an espresso.

So if you want an “American coffee” you have to say that because Italians are very no frills about their coffee and drink a ton of espresso (I’m one of those lame coffee drinkers who puts like 10 pounds (kilos) of milk and sugar in her coffee to kill the bitterness, so don’t judge me.

And I am also the weirdo who brings no calorie sweetener with her on vacation).

Bonus Trivial Pursuit fact, the price of coffee is regulated in Italy and as a result, is kept relatively cheap (helps when you’re doing Italy budget travel).

Therefore, don’t expect to find a Starbucks in Italy any time soon because no one is paying $4.00 for a cup of coffee (Yes to McCafe but a big fat no to Starbucks).

***As a little aside, or side note or handy dandy piece of advice, you typically order/pay for your coffee first and then hand the restaurant employee the receipt.

So hold onto that receipt, otherwise you probably won’t get what you paid for (Story of my life, like when the ATM ate my money or the vending machine ate my sim card. Bastard).

8. Visiting Rome in August

Another one of my mildly brilliant, Italy travel ideas, (In fairness, I didn’t commit this mistake because I was there in December.

But I wasn’t a total social pariah and did crawl out of my shell of social awkwardness long enough to chat with some locals) is to avoid Rome in August since it is as hot as balls (my words not theirs. Can you tell I’m not that classy).

Not only is Rome packed with tourists, but you may actually melt like the damn Wicked Witch of the West.

Literally, every resident of Rome has the month of August off and flees to the beach or a cooler destination because of the insane heat in the city.

Therefore, this is one of those moments where you should follow their lead and not meander through the city with a wicked case of heat stroke (no one wants to get their coma on).

Instead, visit during off season (don’t put it on your summer Italy travel route). Now, naively enough, I thought, “Aww, why would anyone visit Rome for Christmas?

I’ll have the place all to myself”. Lies, all lies and the power of denial. Everyone and their vespa/fiat are in Rome during Christmas because the man, the myth, the legend, the Pope is there.

So while I did have a great time, don’t expect to have the place all to yourself because in reality, you’ll be doing Gladiator style battles for the last scoop of gelato.

But I’m a feisty New Yorker and an avid food addict, I mean foodie, so don’t count me out of a food fight.

9. Forgetting your Cash

In fairness, it’s not like Italy is in the dark ages and uses an abacus to do math and a carrier pigeon to send texts.

They have ATMs and cell phones and computers just like the rest of the world. So yes, credit cards are accepted at most major attractions and stores, but it can be a bit dicey in some of the smaller mom and pop shops.

Plus, many places do have a purchase minimum so if you want to use your card, you will have to spend a certain amount of money.

Cabs also tend to accept cash only so I would always have some on hand, just in case (only a few taxis accept cards and you need to request them in advance).

No, you don’t have to be a Rockefeller and stroll through the city with a wad of cash that makes people think you’re a stripper, but a little extra is helpful in  an emergency.

Actually, you should really carry cash everywhere because no matter where you are in the world, cash will always be accepted, except in some Scandinavian countries, like Sweden, where some stores won’t accept cash at all (hello modernity, do you need a retinal scan?).

*** Do NOT refuse your receipt. By law you must have the receipt within 100 meters of  the restaurant, to ensure that the business has paid their taxes. So unless you want some frantic waiter chasing you down the street, take your receipt.

10. Packing too Much into One Trip

I was in Italy for a grand total of ten days; a vacation that is pretty long by American standards. Throughout those ten days, I saw Milan, Rome, Pompeii, and Naples, and that’s it.

I totally missed out on Florence, Venice, Pisa, beautiful Lake Como, the Amalfi Coast, Sicily, and a ton of other places on my epically long Italy bucket list.

***Brief aside: If you are planning to visit Pompeii like me, definitely get a Pompeii to skip the line ticket. This way, you don’t have to wait in a ridiculous line and you can get some additional information about what you’re looking at. 

Therefore, do NOT try and cram as much into one trip as humanly possible, unless you have a ton of time and are planning a two week Italy itinerary.

I know my natural inclination is to think, “Oh, shiny, new historic city. Must visit since I might never come back.” Yeah, we call this Dory syndrome.

You see a shiny new city and just have to visit, like Lake Como, but don’t! Not only will you spend most of your time traveling, but you will feel rushed and stressed out as you shuttle from one city to the next without enjoying the best wine tours on the Amalfi Coast.

So instead of turning your holiday into the latest season of the Amazing Race, accept the fact that you will not see all of Italy in two or three weeks and focus on spending a lot of time in a few select cities or regions.

This way, you can slow down and actually enjoy each moment of your vacation. Trust me, I have been that maniac who ran from one tour to the next, hopelessly trying to complete her entire itinerary in two days.

I assure you, it is anti-fun and makes your vacation stressful when it doesn’t need to be (Seriously, who am I trying to impress with my vacation resume). So step away from the energy drink and pick out a few cities or regions that you can explore in-depth in depth way.

11. Standing in pointless lines

Why not attend a service instead of standing in line for hours and paying to enter the Duomo just to be hurried through the cathedral because it’s time for the next quota of visitors?

Everyone is invited to attend and politely observe, regardless of their religious views or background, and it’s absolutely free (though leaving a small offering would be a kind gesture).

Additionally, you get the chance to witness these ancient structures being used as intended, with organs playing, candles lighted, incense burning, and more.

You can walk straight in and services normally last an hour or less, so it will probably take you less time than traveling by the typical tourist route.

Most churches provide printed programs with an English translation so you may follow along even though the service will probably be in Italian.

If you feel awkward or uneasy, take a moment to investigate what to anticipate from the service. You may also think about showing there early and asking an usher if there are any protocols or processes to be aware of.

12. Not Dressing Appropriately

Italy is not a very devout or humble country, but many of its attractions are hallowed places of worship, and admittance requires appropriate clothes.

When entering places of worship, both men and women should carry a scarf or shawl to ensure that their shoulders, knees, and elbows are covered. It’s also a good idea to wear closed-toe shoes and long slacks.

If you don’t follow the dress code, you won’t be allowed access. Cutoff jeans and a gorgeous crop top will make you Instagram-ready, but they won’t be appropriate at the Vatican.

Bonus Round

In the grand tradition of screwing things up, when I made my pins I totally forget that I had twelve, and not ten awesome Italy travel mistakes to avoid.

However, I’m super lazy and refuse to redo the pins, so I’m just gonna throw these two last tips in the conclusion and call it a bonus round. Just think of it as your reward for actually reading this post till the VERY end.

So before you go and live a life that is way more exciting than me hiding in my blanket fort, while crying about becoming a crazy cat lady in the not so distant future, here are two more tips for you that will hopefully rock your socks like Tom Cruise in Risky Business.

Numero uno is don’t assume that you can buy bus tickets on the bus because you can’t. If you’re caught without a ticket, you’ll pay a huge ass fine that may lead to depression and financial insecurity.

So proceed with caution and if you don’t see a turnstile or person to validate your ticket, then look for a small box where you can insert your ticket.

Numero dos, wait why am I speaking in Spanish? This is a post about Italy. Okay, moving on.  You know those seedy people that sell knocks offs on the street?

I’m talking about that dude who leers at you and sells you a Bucci that is supposed to be a Gucci purse. Yeah, you’re not allowed to buy things from unlicensed vendors in Italy.

If you do and the police catch you, you will be fined thousands of Euros. So just say nada to the Prada! Okay, I’ll stop because that was really bad.

However, the good news is that you survived this post and that with this somewhat entertaining article, you can also survive any future trips to Italy.

Okay, you’ll totally love Italy even without this post but humor me and pretend like my writing is actually important, kind of like the insanely profound fortune that you get in every fortune cookie (lol). Like the one’s in which Confucius says, “Man who eats whole pineapple eats alone”.

Yeah, I’ve gotten some pretty crap fortunes too (my vane hope is that this post is a smudge better than a craptastic fortune. But the jury still has yet to deliver a verdict. Dun dun dun).