Planning a Trip to Italy: Your Easy 11-Step Checklist

Once you’ve decided to visit Italy, especially for the first time, it’s easy to catch yourself daydreaming daily about sparking blue seas, delicious wine, rolling hills, and ancient cities (and I definitely still do this on a near-constant basis), but successfully planning a trip to Italy requires some not-so-daydream-like steps as well!

From booking transportation to deciding exactly where to go, we’ve outlined all the important steps for planning your Italy trip here.

Use this checklist to ensure that you jet off on your Italian vacation without a single worry!

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Step 1: Check visa requirements.

Based on the geographic readership of this blog, odds are that the vast majority of you will not need a visa to visit Italy for up to 90 days for tourism purposes.

This includes citizens of the USA, Canada, the UK, Australia, and of course, anyone from an EU member state.

Italy is part of the Schengen Zone, and therefore, anyone who needs a Schengen Visa to visit the area will need one for Italy.

Of course, while I strongly doubt that this policy will change in the near future, you should always confirm visa requirements through official sources before traveling!

Update: Can we all take a moment to collectively laugh at that last sentence?

Now more than ever, be sure to regularly check official regulations and track the details of entry requirements!

As of this summer, things in Italy are virtually back to “normal”–but be sure to double-check when booking your trip!

Step 2: Book your trip to Italy!

At this point when planning a trip to Italy, it’s time to make it official and book your tickets to the country!

If you’re flying a long distance or are planning to visit multiple regions in Italy, we recommend being pretty flexible with what airport you fly into in order to get the best flight prices.

Go ahead and check the prices to fly to Rome, Florence, Milan, Venice, and Naples for intercontinental flights.

For shorter flights within Europe, those flying on budget airlines should also check Bologna and Pisa, as well as Bari, Palermo, and Catania if you’re headed south.

Also, be open to the idea of flying into one city and out of another!

While this can sometimes be much pricier, other times it’s surprisingly affordable and allows you to spend less of your trip to Italy doubling back to a city you’ve already visited.

We recommend running the numbers both ways.

Step 3: Choose your Italy itinerary.

This might be both the most fun and most stressful part of planning a trip to Italy: finalizing where exactly you’re going to go!

We have a recommended 2 week Italy itinerary that we suggest for first-timers to the country, as well as our best suggestions for spending a week in Italy, but ultimately, the sky’s the limit!

If you’re looking for the classic Italy experience, a combination of Rome, Florence, Venice, and Cinque Terre makes an amazing first trip.

If you’re more interested in mountain lakes than idyllic coast line, you could swap Cinque Terre for Lake Como.

If you hope to head south from Rome, Naples, the Amalfi Coast, Pompeii, and Capri are all within close distance of each other and make a great addition to a trip or even a standalone vacation.

If you’re hoping for mountains, look at Trentino-Alto Adige–Bolzano and Cortina d’Ampezzo are often the launching pads for exploring the Dolomites.

Beach lovers, consider heading to Sicily, Sardinia, or Puglia.

And, of course, foodies can’t go wrong anywhere in Italy–but the regions of Tuscany and Emilia-Romagna in central Italy are sure to captivate your tastebuds.

Interested in roadtripping? Italy is home to some fantastic road trips, though not every area is suited for it.

Here is our guide to the best road trips in Italy, and our suggested Tuscany road trip itinerary!

Step 4: Finalize your Italy travel budget.

Now that you know exactly when your trip to Italy is happening and where you are going, it’s time to finalize your Italy travel budget!

We recommend taking the total amount you hope to spend in Italy, subtracting any splurges or major expenses you know are coming (a pricey tour, some clothes shopping, etc), and then dividing the remaining amount by the number of days you’ll be traveling in Italy (we detail this strategy more thoroughly in our travel budgeting guide).

Presto–you have your daily Italy budget, aka the number you should try to stay under each day when you add up the amount you spend on food, activities, and intra-city transportation.

Step 5: Book some activities in advance.

Here’s the fun part of planning a trip to Italy: booking those iconic experiences you’ve always dreamed of!

While there are plenty of magnificent things to do in Italy that require little to no advance planning, many of Italy’s most iconic attractions are definitely better experienced by planning ahead to take a tour and/or buy a skip-the-line ticket.

We go into far more detail about this on our guides and itineraries for each specific location, but here’s a quick rundown of some of the major sights you’ll want to book ahead of time.

Rome

The Colosseum

The Vatican Museums

Florence + Tuscany

Uffizi Gallery

Galleria dell’Accademia

Duomo Climb

Venice

Doge’s Palace + Basilica

Shared Gondola Ride

Pompeii

Pompeii Guided Tour

Step 6: Book accommodation.

Next step in planning a trip to Italy: deciding where to sleep!

We offer specific hotel suggestions in our itineraries for each location that we have written about, but here’s the bottom line: in Italy’s major cities like Rome and Venice, it’s fairly easy to find somewhere to stay, so don’t stress about booking months ahead of time unless you have a particular property in mind.

In smaller towns, though–think those along the Amalfi Coast or in Cinque Terre, for example–properties tend to book up a lot faster, and you’ll want to book as far in advance as possible.

We use Booking.com to book hotels and sometimes apartment stays in Italy, and if that doesn’t work out, check out Airbnb for longer apartment stays.

Step 7: Figure out your inter-city transportation.

Now that you know exactly where you want to go, figuring out how to get from destination to destination in Italy–and most importantly, how long it will take and how much it will cost–is the next step in planning an Italy trip.

Note that if you hope to rent a car in the country, you’ll need to obtain an international driving permit before arriving (and double-check that your insurance covers driving in Italy, or purchase a policy that does!).

If you’re planning to take any high-speed trains in Italy, keep in mind that the prices increase as your dates get closer, so book ahead as soon as you’re ready to commit! We use the Trenitalia app to book almost all of our train tickets in Italy.

For regional (aka slow) trains, prices are set and you can just purchase them on the day of travel.

For more on getting around Italy, check out the transportation section of our suggested Italy itinerary.

Step 8: Learn a little Italian.

If you’re staying firmly on the tourist trail on your trip to Italy, you won’t necessarily need to speak any Italian to travel there.

… But you will almost certainly encounter some monolingual Italians, and either way, it will definitely enhance your experience in the country to know a tiny bit of Italian.

We personally don’t choose to carry phrase books with us while traveling, but if you like to, Rick Steves’ Italian Phrase Book gets wonderful reviews.

Here are a few phrases to add to your vocabulary when planning a trip to Italy:

Basic Italian Phrases to Learn When Planning a Trip to Italy

Buongiorno. — Good morning.

Buona sera. — Good evening.

Ciao. — Hello/goodbye. (More casual than above.)

Per favore. — Please. (When requesting or accepting something.)

Grazie. — Thank you.

Prego. — You’re welcome, or please. (When offering something–as in, “Please, have a seat.”)

Non capisco. — I don’t understand.

Parla inglese? — Do you speak English?

Il conto. — The check. (In a restaurant.)

Step 9: Make a packing list (and shop!).

Packing can often be one of the most unexpectedly stressful parts of getting ready for a trip abroad, and Italy is no exception!

You can check out our full suggested Italy packing list here, and our detailed suggestions on what to wear in Rome here (which work for quite a bit of Italy!).

Be sure not to stress too much about packing for Italy, though–just about anything you could possibly forget will be available there too!

Here are a few essentials to be sure to add to your Italy packing list:

Travel Adaptors for Italy — If you’re coming from outside of Europe, you’ll definitely need adaptors for your electronics–don’t forget to add buying these to your to-do list for planning your trip to Italy!

Pacsafe — We can’t recommend our Pacsafe enough: this travel safe is affordable, sturdy, easy to pack, and will help keep your valuables safe in your hotel room (not that you should need to worry much about theft in Italy, but it’s better to be safe than sorry!).

Comfortable Day Bag — We currently use Pacsafe’s sleek anti-theft backpack and love it, but if you don’t want to shell out the cash for this trip, that’s totally understandable.

Just aim for something comfortable to wear, not flashy, and medium-sized–we used a Northface Jester backpack for years and loved it as well.

Umbrella — Option A: Plan on buying an umbrella when it starts pouring down rain. Option B: Plan ahead and buy a (probably much sturdier) umbrella before leaving. Option C: Hope you get lucky with the weather (but fair warning, we’ve never been to Italy and avoided rain entirely!).

Reusable Water Bottle — You’re definitely going to want to carry water with you as you explore Italy (especially during the hot summer). Cut down on plastic waste and bring a reusable water bottle instead!

Purell Hand Sanitizer — We’ve never been sorry to have this floating around in our day bag.

Money Belt — This is up to you: we no longer use one, but if you’re more comfortable having your passports on your person in Italy, you can consider bringing one.

We used to use this one and had no complaints. These days, we prefer just to leave valuables in our Pacsafe during the day.

Step 10: Purchase travel insurance.

Don’t forget to purchase travel insurance before jetting off to Italy!

While Italy is a perfectly safe country to travel in, traveling in general opens you up to vulnerabilities that you simply don’t have at home: if you miss a plane or train, have your luggage get lost, get pickpocketed, or worse, get injured, you’ll be glad that you have insurance.

Given how inexpensive travel insurance is when purchased in advance (especially as compared to the price of plane tickets to Italy!), it’s well worth the investment.

Check travel insurance policy inclusions and prices for your trip here.

Step 11: Make your arrival plan.

The final step of planning a trip to Italy is as simple as it is important: make an arrival plan.

When you arrive in Italy, you’re undoubtedly going to be exhausted, overwhelmed, and probably a bit jetlagged, too!

No matter how many times we arrive in a new country, it never stops being a tiny bit stressful, simply because there are a lot of variables at play in the first few hours of arriving somewhere new.

Make life easier on yourself by thinking ahead: when working on your trip to Italy plan, figure out your exact steps of what will happen after the plane lands.

That means exactly how far away your hotel is, how you’ll get there from the airport (train, bus, rental car, taxi?), and if you’ll be traveling by taxi, what a reasonable price is and/or if there’s a set fare from the airport to the city center (in Italy, there often is).

Though it’s not strictly necessary, if you’d like to make arriving in Italy extra-easy for yourself, consider treating yourself to an airport transfer when you arrive!

Rome

Shuttle Bus from Fiumicino Airport to Roma Termini

(Bear in mind that while this is actually cheaper than taking the Leonardo Express train independently, it does also take longer to get to Rome!)

Private Transfer from Fiumicino Airport to Rome

Florence

Private Transfer from Florence Airport to Florence

Venice

Shuttle Bus from Marco Polo Airport to Venice

Shared Water Taxi from Marco Polo Airport to Venice