The Best Way to Plan Your First Trip to Italy

Where to visit, where to go, and where to stay in Italy for the first time

You, finally on that trip to Italy.

I'm going to go ahead and be honest, there's no one-size-fits-all itinerary or plan for Italy. Personally, I think this is a good thing, it allows you to have the perfectly-tailored trip for you.

However, I'm not the one taking the trip, so it's really up to you. And if you're only going to Italy to "cross it off the list", or because your friend group recently went on a trip without you and now they won't stop talking about it, and you're starting to feel left out, that makes perfect sense. Seriously. And they suck for not inviting you.

Regardless of why you're going to Italy, the fact remains, once you've decided to go, it's still a major question of, "Now what?".

This is where we come it!

How to plan your first trip to Italy

There are many ways, and instead of telling you where to go (though, we might make some example itineraries later), it's better to teach you why.

For ease, let's start by assuming you don't have any firm goals or aims in mind. You're not sure what there even is in Italy, so you're not sure what you should plan on seeing. Before I first came to Italy, that was me. I knew that Rome had a Colosseum, and Venice had canals, and that was about it. I didn't really know much about Florence, didn't realize the Amalfi Coast or Cinque Terre were actual places, and my mental image of Italy was pretty much the set pieces from Under the Tuscan Sun.

So, that brings us to the first step of planning your first trip to Italy. So many firsts!

Step 1: Figure out what you like

This is a great time to say: Unless you have more than a month, or you don't sleep, you probably can't see everything on your first trip to Italy. Italy is larger than you think it is, and transportation—while incredible—can't connect you from the south to the north in an afternoon.

This is where I like to start with some general questions.

But first...

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Should I go to either Sicily or Sardinia on my first trip to Italy?

It makes sense to want to move off of mainland Italy onto one of Italy's major islands. However, if this is your first time to Italy, I'd highly suggest you stick to mainland Italy. Sicily and Sardinia can only be reached by plane or ferry, and unless that's part of the enjoyment for you (a ferry trip can be quite the experience!), it can add a lot of unnecessary travel time that could be better spent doing something lese.

That said, if you can, you should absolutely consider traveling to both of these islands, and potentially centering the trip on them, rather than "Italy" in general.

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Now that we've covered that, let's jump into it!

Modernity vs. History in Italy

This is how I like to consider the question of "Rome vs. Milan". Milan is a city, and a fairly new one. It has a beautiful church and some interesting things to do, but it lacks the soul of Rome and Naples, and it's "old town" isn't as impressive as you might find elsewhere. However, there's tons of shopping, plays, shows, musicals, and everything else you might want from a metropolitan city, including top-tier cuisine. Likewise, it's close to the rest of Europe, so if your trip is also taking you into France, Germany, or Austria, then Milan makes sense as a base.

However, if you want to see one of the two beating hearts of Italy, then Rome is your best bet as a home base. It has tons of history, little streets filled with shops (and main streets filled with larger, more recognizable brands like Prada and H&M), and fantastic food. Rome is, for most people, the obvious starting place. It has a little bit of everything, and if you've been to Rome, then you've been to Italy.

Whichever city you choose acts as the "home base". This doesn't mean you spend all of your time there (though, let's be honest, a week in Rome isn't nearly enough time), it only means it's your starting place or your ending place, and the place you'll spend the most days in a single stretch (or, two stretches, if you prefer the loop method to the line method, more on that later).

Beach vs. Mountains in Italy

Of course, you'll need to do more than just see one city, so this is where you can choose between the beaches or the mountains.

Italy is obviously well-known for it's beaches, seeing as it's practically made up of only coastline. However, what you might not know is that the interior of Italy is pretty much only mountains. In the north there are the Dolomites and from there, running all the way south, there are there Apennines. While there are some flat areas in Tuscany and Puglia, it's all mountains everywhere else.

So, do you prefer swimming, snorkeling, sunbathing, and sailing? Or hiking, spelunking, camping, and forest-bathing?

Whichever category you fall into, there are plenty of options on the table. From the Amalfi Coast or Cilento Coast for swimming, to the Aosta Valley or Piedmont region for a hike.

Winter in Italy

If you're planning on coming in the winter, then this whole "beach or mountain" thing isn't really much of a question. While Italy has this reputation of being sun-filled year round, it's not true. And it does get cold. And the beach towns turn into these miserable, little towns filled with winter storms where nothing is open (speaking from experience here). While you might be able to get an amazing rate on a winter hotel in southern Italy or Sicily on the coast, it's not going to be a very fun time.

Instead, take to the mountains! Explore skiing in the Dolomites, or Krampus-filled festivals and Christmas markets, or the ever-popular Venice Carnevale (the one exception to seaside town).

Walking vs. not walking in Italy

If you're able to walk and you enjoy it, Italy is the perfect country for you. Everything, and every city, is a series of hills, slopes, and places impassable by car. From Positano to Venice, your feet will be your best friend. When I say walking, I really do mean walking. Uphill, mostly, somehow. And constantly. It's usually going to be far easier to walk somewhere than take public transportation.

I really want to make this clear because I've often found that the number 1 surprising thing for people who haven't visited Italy is the amount of walking involved. I can't tell you the number of times people said something like "Even though we ate so much every day, I still lost weight because we walked so much". And this will probably happen to you, especially if you're picking walking-heavy cities.

Of course, if you're not a huge fan of walking, or if you're unable to (or unable to easily), then you will find that Italy is sadly not that accessible. That said, there are pushes and initiatives to makes things more accessible, so in cities like Florence, Rome, Milan, and to a certain extent, Siena, there are plenty of flat areas that can be more easily managed, or even explored through a rented golf cart. However, sidewalks still don't have a little slope/ramp so even if the sidewalk is flat, you can't easily cross the road to get onto the next sidewalk.

Northern Italy vs. Southern Italy on your first trip to Italy

This is a completely valid way to see Italy, breaking up the country into North and South, with Rome as the dividing line.

However, this does require a bit of geographic knowledge of Italy, first and foremost, since if you don't know where anything else, it's almost impossible to know what's north and what's south.

This said, and I want to be super honest, a trip to Northern Italy will have tons to see. A trip to Southern Italy will have far less to see. Not because there's less in Southern Italy (though, arguably, there is), but because it's not as "tourist-ready". For those who are interested, I'm working on a "North vs. South" article, and when it's ready, I'll link it here!

Now, let's get a little bit more specific.

Step 2: What are some extras you would like to do?

Should you see art in Italy?

This seems like a pretty simply question, but if you're into art, then you're coming to the right country! Seat of the Florentine Renaissance, and all. Plus, there are some pretty cool Greco-Roman sculptures kicking around (the Farnese Collection). So, you have to check them out, right?

Absolutely! But only if you're into art. If you're the type of person who says, "Yeah, it's nice to see a painting occasionally." then I wouldn't suggest making plans to see the Uffizi or Academia. The tickets are expensive, the lines are long, and (like all museums) they're designed to keep you inside. Or is that casinos? Either way, unless you're into seeing some art, or you love museums, I wouldn't necessarily recommend hitting up any art museums "just because".

That said, if you are into art, then it's clear you should be spending some time in Florence at an absolute minimum. Potentially even Siena. Rome has a some great art museums, as does Naples. And the "Last Supper" is in Milan, if that strikes your fancy. As I said, there's a lot of art in Italy. But to make it simple, if you're into art, go to Florence.

Should you see a soccer game in Italy?

This is in the same category as art and museums—it kinda depends. Some soccer teams will only sell tickets to non-association members a day or two before the game, so it's not something to plan on (this is more common with club games).

You should probably also consider seeing a soccer game as a half-day experience at minimum. Between transportation, getting your ticket checked, finding the seats, enjoying the game, fighting to get out, fighting for the bus/taxi/Metro, and leaving, it's an involved process.

So, again, I'd only recommend this if you've been following Napoli for a while and are huge fans, or you love McTominay and would love to see him score against AC Milan. As a simple "on a whim" type thing, it can be a lot to arrange, so it might be best to leave it to the second trip.

This all said, if you want to see a game, consider Milan, Rome, or Naples for some of the larger teams with larger fandoms, which make seeing a match more of a religious experience.

Do you want to get off the beaten path in Italy?

This is going to sound a bit controversial, but you really don't want to get off the beaten path if this is your first trip to Italy.

Step 3: The Plan

Now that you have an idea of what you might want to see, let's talk about the two easiest methods of geographically planning your trip.

The Line Method of Planning Your First Trip to Italy

This is exactly what it sounds like, and it's making a Point A to Point B line from where you want to start to where you want to end up. Typically this means going north or south since there isn't a whole lot of "east and west" in Italy.

This methods makes use of the "multi-city" type of ticket, instead of the roundtrip. For those of you who aren't sure what that is, a multi-city ticket is a bit like Point A to Point B, and Point C to Point A, where Point A is your hometown airport. For some, you can make it even more "multi" than that, leaving from one airport and coming home to another.

So, to use real city examples, let's say you live in New York City. A "line method" plan would look like this:

Fly from NYC to Rome.

Travel through Italy.

Fly out of Venice or Milan back to NYC.

Benefits of the Line Method:

No backtracking: This is the biggest benefit to using the line method. You won't be going back over the same territory, or wasting a day on the train going from Venice all the way back to Rome.

Could be cheaper: Using the line method, you won't have to spend that extra money on a train back to where you started. Likewise, you might find flights are cheaper into one airport but out of another which is why it's always important to look.

The Loop Method of Planning Your First Trip to Italy

The other method of planning a trip is the loop method, which means you would start and end in the same city.

This method uses the roundtrip ticket, and relies more on you not going too far away from your base city.

Benefits of the Loop Method

Could be cheaper: Again, it's important to look, but sometimes a roundtrip ticket is cheaper than a multi-city.

Crowd favorites: If you had a restaurant, café, shop, or city you really enjoyed, this is a way to enjoy that place one last time before you leave. This could be especially important for those of you who like to see a few cities and then buy gifts at the very end of the trip, or for those of you who only want to see a few places but really get a sense of the lifestyle there.

Last Thoughts on Planning Your First Trip to Italy

Sometimes, the easiest way to plan the trip is to build it around a single thing. A pastry, a dish, a painting, an activity, whatever it is, and then build up the rest of the trip around it, especially if the idea of going to Ital is overwhelming.

Just know that just like there is no right way to plan a trip to Italy, there's no wrong way either. If you're coming just to try the pizza in the birthplace of pizza, or to finally see Michelangelo's David, then it's going to be the perfect trip!

Now that you have an idea of how to get started, everything else will come easier!