Italy for the First Time: How to Plan Your Trip

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Without a doubt, traveling to Italy for the first time is exciting and overwhelming. Going to Italy is even considered a lifelong dream. When asked about their number one travel destination, a lot of people will mention Italy right away. It feels as if everyone loves, loves, loves Italy.

I fall into that mindset too. When I was in college, I dreamt of studying abroad in Italy if I couldn’t study in France (spoiler alert: neither happened). Italy enticed me. Handsome men, flawless fashion, Renaissance art, and food. Oh god, the food. Italian food is a gift from the heavens. 

And you know what? Even if I also hadn’t been obsessed with Italy, I would’ve still understood this almost universal fascination with this boot-shaped country. 

For instance, in the United States (where I live), so many people are able to trace their family’s history back to Italy. The Italian diaspora reached far and wide, especially to northeastern cities such as New York and Philadelphia. It seems like almost everyone I run into claims Italian heritage. 

Italy for the First Time is Magical

In this guide, I want to help you plan your very first trip to Italy. I’m lucky enough to have visited Italy twice, once with a group and once alone, so I feel as if I’m in a good position to help you prepare for your upcoming Italian adventure. 

Preparation is key for a great trip to Italy. However, although I’m going to cover a lot of practical tips in this guide, I don’t want you to feel an immense amount of stress or anxiety before your Italian trip.

Believe it or not, Italy’s one of the easier countries to travel in Europe.

But what if it’s your very first vacation to Europe? Is Italy a good option to start with? 

Is Italy Good for a First Trip to Europe?

Let’s say you’re going to Europe for the very first time. Is Italy a good choice? Or should you start somewhere else such as Scotland or Ireland?

Honestly, I think Italy is a great choice for taking a first trip to Europe. Post done! 

Hahaha, just kidding.

But, in all seriousness, Italy is a wonderful way to start exploring Europe as a whole. I wouldn’t make this statement about all the places I’ve visited, either.

For example, I think Paris is more challenging than it seems at first glance, and is much better for visitors who already have a couple international trips under their belts. But Italy, on the other hand, is fantastic for new travelers!

First of all, Italy is very used to tourists. If you take the traditional Rome-Florence-Venice trail, then you’ll encounter plenty of English speakers. There’s also fantastic tourism infrastructure in place for public transportation and major attractions.

And it’s very unlikely you’ll encounter destabilizing issues such as food poisoning or intense culture shock. 

Furthermore, most people have a beginners’ understanding of Italy’s culture.

For example, Italian food is widely appreciated around the world. We’ve all heard of the Romans and their impact on history. In a lot of ways, Italy “feels” familiar even if you’ve never stepped foot in the country. 

So, yes, go to Italy for your first trip to Europe. 

Where to Go for Your First Trip to Italy

Italy has so many cosmopolitan cities, medieval towns, and natural wonders that it’s impossible to see the entire country on one week long visit. 

I prefer to split Italy into regions. For example, I wrote all about how to spend 8 days in Northern Italy, and didn’t mention any city further south than Parma. 

Your first time trip to Italy should be all about you and your interests. Still, a lot depends on your comfort level. 

Let’s say you’re exceptionally anxious about traveling abroad. Then I would either recommend taking a guided tour, or sticking to the most popular tourist route, which is Rome, Florence, and Venice. In those three cities, you won’t be the only solo traveler. You can also sign up to do a lot of fun activities and make new friends with fellow visitors. 

On the opposite side, if you’re confident, it pays to escape to some of the lesser known cities and towns in Italy. Less tourists mean cheaper prices and more relaxing experiences. For instance, I loved seeing the seaside town of Camogli in April and felt as though I were a Romantic poet doing a classic European tour. 

Lastly, you want to consider the time of the year for your first trip to Italy. You might not want to go to southern Italy in the scorching heat of summer or to Lake Como in the middle of January. 

Italy for the First Time: Before You Leave Home

Ready for some more trips? Of course you are!

Now I know you’re absolutely pumped about exploring Italy for the first time, but you need to have all your priorities in order before leaving home. 

1. Call Your Bank Ahead of Time

Do. Not. Forget. To. Call. Your. Bank.

I’m so, so, so super serious. 

The best exchange rates are always found at ATMs. However, you won’t be able to use your ATM if you bank is clueless about your travel plans. Give them a ring, and provide them with specific dates and countries. You’ll even need to tell them about layovers in case you’re delayed on the way to Italy and unexpectedly need to access your checking account. 

Additionally, thanks to rampant fraud, credit card charges won’t automatically go through in a foreign country. Your credit card company needs to know about an international trip so they don’t block all purchases. 

So, yeah, call your bank or else. 

2. Make Important Ticket Reservations 

Argh, Italy’s popularity is a double-edged sword. Meaning while the infrastructure is great, insane crowds gather at the biggest attractions. You don’t want to waste your time standing in useless lines or prevented from seeing masterful works of art, because you didn’t plan in advance.

Luckily, you have a lot of options for skipping lines at the most crowded attractions, such as Rome’s Colosseum or Vatican City’s Sistine Chapel. Booking ahead with a tour group will keep you from standing in line for two hours. Cause, really, who has time for that nonsense? Not me or you.

Furthermore, some tourist sites actually require reservations ahead of time. For instance, tickets to see DaVinci’s The Last Supper need to be booked several months in advance, especially in high season. Otherwise you might miss out! 

3. Learn a Few Phrases of Italian 

English is widely spoken in the bigger Italian cities, especially ones that draw a lot of international tourists such as Milan and Rome. You won’t encounter much of a language barrier in these places. 

Yet it’s always polite to learn a couple of essential Italian phrases to use with wait staff and tourist guides. Speaking Italian is a sign that you respect the culture, country, and local people. 

My advice is to grab a quality Italian phrasebook, and do a little reading on the flight over to Italy. That way the words are fresh in your mind. 

If you have a good data plan, you can also install Duolingo on your phone and practice Italian on a regular basis. I think Duolingo is a fun way to learn a new language outside of a classroom.

4. Read About Italy’s Great History & Art

Italy’s so culturally rich that it’d be a shame to take a trip without any prior knowledge. Learn about Italy’s great art, history, and culture. 

For example, I love watching historical documentaries, many of them free on YouTube, before I take a big trip to a new country. 

Why is it so important to study ahead of time? Because Italy is packed with art. The amount of art in Italy will literally make your head spin off its neck. If you go in blind, you might miss out on some great masterpieces or miss out on certain museums that would speak to your creative side.

In my opinion, by reading ahead of time, you’ll know what masterpieces you want to see on your trip to Italy and allot your time in the best possible way. 

Safety Tips When Visiting Italy for the First Time

Time to talk about safety.

Ugh, I know, I know.

Even though it’s not fun to consider, you probably want to know all about safety when going to Italy for the first time. After all, although taking an international trip is rewarding, you don’t want to end up in a bad situation so far away from the comforts of home. 

Honestly, Italy is a very safe country that’s very used to tourists. You don’t have much to worry about especially going into your trip armed with knowledge. 

1. Be Firm if You’re a Solo Female Traveler

Firstly, I encourage women to travel alone in Italy. This country is a dream destination for many people, and you shouldn’t not go simply because you’re a a solo traveler. I went to Italy alone and had zero issues with harassment. 

I’m gonna keep it real and honest here, ladies. Most annoyances will come from Italian men who might whistle or yell compliments to you in the streets.

The best thing to do is ignore it. Duck into a shop or restaurant if someone turns aggressive. As women, the idea of being “polite” is constantly jammed down our throats, but I’m here to give you full permission to brush off these over the top “compliments.” You don’t owe these men anything. 

Fortunately, blending in with locals (sometimes) helps here. Now I don’t think anyone’s choice of clothing grants permission for sexual harassment. Women should be able to wear whatever they want. And street harassment is never, ever the woman’s fault.

However, still opt to dress a tad more modestly and wear subdued colors such as blacks and grays. You’ll probably feel more comfortable and attract less attention. 

2. Don’t Drink Too Much Wine

Italy’s known for its wine. And it’s delicious.

However, getting drunk in an unfamiliar country isn’t the greatest idea of all time. Still enjoy Italy’s wine, but limit yourself.

Personally, I think two or three drinks is plenty for a dinner out. Ask the servers for wine recommendations. The restaurant’s local “house” wine is usually the best deal. 

You also want to limit your wine intake, because having a hangover and sightseeing is far from enjoyable. Don’t ruin your vacation over alcohol.

3. Wear Proper Footwear for the Italian Hills

Are you a hiker? Then going to Italy for the first time will be a wonderful experience, but don’t skimp on proper footwear. Don’t you bloody dare! 

For example, in one of Italy’s most popular hiking destinations, tourists have been fined a substantial amount of money for inappropriate footwear. Harsh? Perhaps, but it’s also unfair for emergency services to rescue you for wearing lousy flip flops in the rugged hills. 

Bring a pair of trekking sneakers for those hillside hikes. You’ll protect your feet and your wallet at the same time. 

4. Stay Aware of Pickpockets & Tourist Scams

Unfortunately, Italy has its fair share of scam artists who love to target naive tourists. It sucks, but scammers are a reality of traveling in Italy.

Since you’re reading this post, you’re already more informed than the average visitor. My honest advice is to avoid anyone who tries to give you a gift or sell you something that you didn’t ask for. Be wary of anyone shoving unsolicited advice down your throat. Don’t accept flowers from strangers. Ignore any and all sob stories. 

As I’ve said, you don’t owe anyone politeness, especially if they brush aside your wishes to be left alone. 

As for pickpockets, don’t feel paranoid, but stay aware in crowded areas near major attractions and on public transportation. Keep your hand on the zipper of your purse. 

If the thought of pickpockets will ruin your trip, then I recommend investing in an anti-theft bag such as this crossbody bag by Pacsafe. 

5. Keep Your Distance from the Roma

In Italy’s big cities, you’ll likely see Roma women and children begging on the streets. They might even tug at your heartstrings. I absolutely hate seeing struggling students in particular. I think of my own students and the thought breaks my heart into pieces.

So, trust me, I feel bad for the plight of the Roma too, and feel as if they are horrifically discriminated against on a systemic level.

However, keep your distance, and don’t open your wallet to the Roma. The women and children do not get to keep this money to benefit their families. Instead they fork the cash over to the men in charge. And the cycle continues. 

Let me repeat that. By giving money, you’re contributing to a system that encourages exploitation. Don’t do it. 

6. Avoid Renting a Car – Use Public Transit Instead

Driving in Italy terrifies me. And I don’t consider myself a bad driver either. I live in one of the most densely populated areas of the United States. 

And I still wouldn’t drive in Italy. You couldn’t pay me enough to attempt it. 

Ditch the car. Instead use Italy’s extensive trains and buses to get around the country. I thought that Italy’s trains were clean and comfortable, and honestly, ticket prices are reasonable compared to other European countries. 

Reserve tickets ahead of time on the “fast” trains. You are given a designated seat. For local trains, either buy tickets ahead of time or purchase them right at the train station. 

I hope you found my guide on visiting Italy for the first time helpful. What suggestions would you give to a traveler taking his or her first trip to Italy?