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How to Plan a Trip to Italy: Step-by-Step Guide

How to Plan a Trip to Italy: Step-by-Step Guide

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Dreaming of your first trip to Italy? Let me show you exactly how to plan a trip to Italy like a pro!
This post about how to plan a trip to Italy for the first time was written by family travel expert Marcie Cheung and contains affiliate links which means if you purchase something from one of my affiliate links, I may earn a small commission that goes back into maintaining this blog.

Are you itching to visit the land of La Dolce Vita and want to know how to plan a trip to Italy?

You’re in for a great trip! Italy has tons of iconic cities, charming coastal resort towns, alpine mountains, utterly delicious cuisine, and plenty of world-class attractions.

But navigating first-time travel to Italy can be overwhelming. There are just so many destinations and things to do, how do you know which are the best places to visit in Italy for first-timers?

And what about the best time to travel? Or how to get around? Or the little details that travelers embarking on their first time to Italy will inevitably miss?!

This simple ‘Italy for Beginners’ guide will take you through everything you need to know about how to plan an Italian vacation, step by step.

15-Step Guide on How To Plan a Trip to Italy

Step 1: Check Your Passport and Visa Requirements for Italy

If you are from the US, you can most likely apply for an ETIAS visa waiver for the 27 EU countries in the Schengen area. 

Italy is one of these countries. It’s a simple online form that will allow you to spend up to 90 days at a time in a Schengen-area country.

How to Apply for a US Passport for a Baby or Child, tips featured by top US travel blogger, Marcie in Mommyland: Learn how to get a passport for a child (or baby) with these 8 easy steps. You’ll even find some secret, expert tips to help expedite the application process
Make sure your passport has at least 6 months left on it before it expires.

You may not be able to apply for a visa waiver until you’ve booked accommodations as you’ll need to input the address. Just remember to apply once you have that information!

Another of the most important things to know when traveling to Italy is that you need six months of validity on your passport. Now is the time to get your passport renewed if it’s about to expire.

Speaking of passports, you’ll need to carry your passport in Italy at all times.

Step 2: Figure out the Length of Your Trip to Italy

Due to limited vacation time, school breaks, and everyday adult responsibilities, you probably already have a rough idea of how long you have to spend in Italy.

If you’re flying long haul, your trip should be at least five days but the longer, the better. 

When visiting Italy for the first time, you’ll want to spend as much time there as possible!

Step 3: Research the Best Time to Travel to Italy

Researching the best time to travel to different regions in Italy will also help when figuring out how to decide where to go in Italy. 

Annual events, average climates for different seasons, and popular travel seasons are all factors to consider.

For example, you absolutely do not want to visit southern regions like Sicily or Calabria in summer. Temperatures often climb above 104°F/40°C!

Southern Italy and the Italian Alps are perfect fall/winter destinations.

My youngest LOVED riding a gondola in Venice! Photo credit: Marcie Cheung

Easter and Carnival are great times to visit cities like Florence and Venice for unique religious celebrations. However, some of the top attractions might close for the holidays. 

Parents with school-age kids might only have the summer months to travel. Stick to northern, coastal regions like the Italian Riviera or the Lakes like Como and Garda to avoid the worst of the heat.

Keep in mind that everywhere in Italy is more expensive in summer. The shoulder seasons of April – June and September – October offer fewer crowds and cheaper accommodations.

Step 4: Choose Your Italy Destinations

Time for the fun part: choosing destinations for your dream Italian vacation!

Some of the best cities to visit in Italy for the first time include Rome, Venice, and Florence. They have the best international airports and the best infrastructure and attractions for tourists, with many day trip options.

Image of a family selfie at the Leaning Tower of Pisa in Italy
Quick family selfie at the Leaning Tower of Pisa! Photo credit: Marcie Cheung

You can easily visit Naples on a day trip from Rome. Pisa is less than an hour from Florence, and Verona is close to Venice.

If you have 10 days, two weeks, or more to play with, visit a whole region! Take a road trip through Sicily or tour around the lakes and coastal towns like Cinque Terre in Northern Italy.

Step 5: Create a Budget for Your Italian Vacation

Your budget will depend on the size of your family, your travel style, the time of year you are traveling, and what you can afford. Most guides will agree that a ballpark figure for a family of four is around $1,000+ for a trip that is at least one week. 

You may have the budget to take some day tours or join a small-group tour. This will make it much easier for you to plan your Italy itinerary.

Want to know how to plan a trip to Italy on a budget? Book airfare months in advance and stay in cheaper short-term rental apartments outside of the historic center.

Italy has phenomenal delis and bakeries. Make picnics for lunch or cook dinner so you don’t eat out at restaurants as much.

Step 6: Book Your Flights to Italy

If you’re traveling to Italy for the first time, there are some airports in the US that fly directly to Italy. Naturally, most of these are on the East Coast!

Traveling on a Budget: 25 Cheap Travel Tips Every Family Should Know About featured by top US family travel blogger, Marcie in Mommyland
Check around for the best flight routes and prices.

New York, Chicago, Washington, Atlanta, and Philadelphia fly directly to Rome, Milan, and/or Venice via ITA Airways, Delta, KLM, or Air France. 

Since Italy is such a popular destination, it’s usually easy to find connecting flights either in the US or another travel hub in Europe.

Return economy flights to Italy from the US can cost anywhere from $600 to $1,500.

Step 7: Plan Your Italian Vacation Itinerary

How to plan an itinerary for your trip to Italy really depends on where you are going. Here are some tips for popular Italian destinations:

  • How to plan a trip to Rome – Book the top attractions first (Colosseum, Vatican Museums, etc.). Plan the most popular free activities, like visiting the Trevi Fountain, early in the morning to avoid crowds.
  • How to plan a trip to the Amalfi Coast – Hop around and visit a few different towns like Sorrento, Positano, and the Isle of Capri. Spend as much time swimming in the sea or sailing as possible and book a room with a view of the hillside houses.
  • How to plan a trip to Venice Italy – Avoid cruise ship crowds by exploring the city early in the morning or late at night. Take a gondola ride when you first arrive to see the highlights.
  • How to plan a trip to Cinque Terre – Stay in one of the five towns and buy a rail pass to travel between all the villages.

It’s great to have a rough idea of the top things to do in a place, but don’t overplan your days hour-by-hour. You’re on vacation, not in school! 

Leave some time for relaxing and sipping cappuccinos while people-watching in piazzas.

Step 8: Book Accommodation in Italy

The next step when you plan a trip to Italy is to book your accommodation.

You’ll find a range of chain hotels, guesthouses, and short-term rentals all over Italy. For a unique cultural experience, consider staying in an agriturismo. These are bed and breakfasts that also grow produce like lemons, olives, or tomatoes.

Image of a boy with suitcases in front of the Hotel Bisanzio in Venice Italy
We loved staying at the Hotel Bisanzio in Venice! Photo credit: Marcie Cheung

If you’re traveling to Italy for the first time, note that all accommodations charge a daily tax. It’s between €0.50 to €3 per person with a cap of €15 depending on where you stay.

Here are our favorite kid-friendly hotels in Rome, Florence, and Venice.

Step 9: Book Transport or Rent a Car

Traveling around lots of destinations and want to know how to plan a multi-city trip to Italy? 

Two of the best ways to see Italy are trains or rental cars!

Italy’s Trenitalia rail network is affordable and easy to use and services between major cities are comfortable and fast. If you are planning a city-hopping trip to Italy, trains are a great choice.

Image of a boy looking out the window on a train from Venice to Florence
This was our train from Venice to Florence. Photo credit: Marcie Cheung

Here are our favorite day trips by train from Rome and Florence.

Rental cars are the best option when traveling through more rural areas like the Tuscan countryside, the lakes, or Sicily. 

Book early to secure one with an automatic transmission if you’re traveling from the US! Most Italian drivers use manual so they are in short supply.

Step 10: Purchase Attraction Tickets and Plan Activities

You’ve created your itinerary, now it’s time to make sure it becomes a reality!

Many of Italy’s top attractions attract thousands of people every day. Wait times for the Colosseum in Rome and the Statue of David in Florence often exceed 90 minutes and some attractions, like The Last Supper in Milan, sell out weeks in advance.

Image of a boy at the Colosseum in Rome Italy
I’m SO glad we had skip-the-line tickets for the Colosseum! Photo credit: Marcie Cheung

Save yourself the headache and book tickets to the most popular attractions Sometimes, it’s worth booking guided tours for free attractions just to avoid the lines.

Step 11: Organize Travel Insurance for Your Trip to Italy

Ideally, getting travel insurance should be an early step in this guide on how to plan an Italy trip. 

If you buy it just after you book flights, you could claim on your insurance if you have to change or cancel your trip at any point.

But the main reason why you should get travel insurance is to cover any medical expenses in case of an emergency while in Italy. So, as long as you get it before you fly, your health will be protected.

Step 12: Figure out Phone, Credit Card, and Currency

Money and internet connection are two important considerations when planning an Italy trip. Exchange some cash for Euros as it’s always a good idea to carry some, but you can use a card for most purchases.

Euro money: closeup of banknotes and coins
It’s always helpful to get some Euros in cash.

Whilst Visa and Mastercard are widely accepted in Italy, American Express isn’t. Take an alternative just in case.

Consider getting an eSIM so you will have data on your phone when you’re out and about. Some Italian cafes and public spaces have WiFi, but not all.

Step 13: Research the Best Italian Food and Restaurants

You don’t want to waste any stomach real estate eating average food when it’s your first time in Italy!

Each of Italy’s 20 regions has its own unique cuisine. Eat at restaurants pizza in Naples, pesto on the Italian Riviera, and carbonara in Rome. Book a cooking class to learn how to make these delicious dishes at home.

Image of a boy holding gelato in front of an oversized ice cream cone in Rome
Gelato is ALWAYS a good idea! Photo credit: Marcie Cheung

Let’s face it, the best place to visit in Italy for first-timers is any gelateria that serves delicious homemade gelato. 

Top tip: Even the smallest size of gelato usually means you can get two flavors!

Step 14: Watch Movies and Read Books Set in Italy

After you’ve finished your Italy travel plan, spend the rest of your time reading books and watching movies set in Italy. It will make you even more excited for your trip!

Some recommendations are Eat Pray Love by Elizabeth Gilbert, Under the Tuscan Sun by Frances Mayes, and A Room With a View by E. M. Forster. Or you can watch the movie versions if you’re short on time.

Step 15: Go To Italy!

Once you’ve finished planning your trip to Italy, all that’s left to do is enjoy your vacation. 

Try not to stress too much if things don’t go to plan. Treat yourself to a gelato cone and your outlook will soon get brighter.

Planning a Trip to Italy FAQs

Why Travel to Italy?

There are so many reasons why you should travel to Italy because it offers something for everyone!

Italy boasts several wine regions, unique cultural festivals, and an abundance of world-class art and museums. You’re never far away from the coast and Italy has plenty of seaside resort towns, lakes, winter sports regions, and hiking trails.

The cities in Italy have beautiful architecture and the country is famous for its crowd-pleasing cuisine with staples like pasta, pizza, and gelato. 

Rome, Venice, and Florence are, in particular, some of the best places to visit in Italy for the first time.

How much does a trip to Italy cost?

It’s incredibly difficult to give a definite answer on how much a trip to Italy costs as it depends on your travel style and the time of year you are traveling.

On average, economy airfare to Italy from North America can cost around $600 – $1,500 per person. Daily expenses in Italy could cost between $75 – $300. 

Families of four might expect to spend the equivalent of $1,275 per day on a vacation in Italy.

How far in advance should I start planning a trip to Italy?

When researching your first trip to Italy itinerary, you can start planning as early as you like! 

Book your flights at least eight months in advance to get the very best price and your pick of accommodations. You’re more likely to snag tourist attraction tickets that sell out, like The Last Supper by Leonardo da Vinci in Milan, if you’re organized.

If you’re less organized, you can still easily plan a trip to Italy with two to three months’ notice.

How To Plan a Trip to Italy Wrap-Up

Figuring out how to plan a trip to Italy is really straightforward once you know the steps.

You won’t fall into the common mistakes many travelers make, like visiting Sicily in summer or avoiding Italy’s surprisingly great rail network.

All you need to worry about is packing your sunglasses and enjoying your incredible trip!

Looking for more Italy travel resources? Check out my 10-day Italy itinerary for families, 8 Incredible Amalfi Coast Bucket List Experiences, Rome travel tips, Florence travel tips, Venice travel tips, 3 days in Rome with kids, day trips from Rome, 2 days in Florence with kids, kid-friendly Rome tours, day trips from Florence, day trip to Cinque Terre, Europe travel tips, and 1 day in Venice with kids!

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