Planning a Trip to Italy

Planning a Trip to Italy

So you’re planning a trip to Italy! Congratulazioni! The planning stages are always so exciting, but can also be overwhelming. We created this Italy trip planner to help you get started and stay organized. If it’s your first trip to Italy, this guide will be a huge help to get you started.

We’ve done Italy trip planning for hundreds of clients and for ourselves over the last ten years. In recent years we couldn’t keep up with the demand that clients had, so we created this guide to help those who we couldn’t personally help. This will walk you through planning your own trip to Italy and help you stay on track, making sure you’re not missing anything important.

Enjoy planning a trip to Italy with ease and fun!

Decide When to Visit Italy

The first step is deciding when to visit Italy. This will depend on your own personal schedule and budget, but there are a lot of things to take into consideration.

When is the best time to visit Italy?

Winter – Winter is a very affordable time to take an Italy trip. Flights and accommodations will both cost less. You will also be battling fewer crowds during your time there. If you are interested in winter sports, winter is a great time to consider northern Italy itineraries. If you’re a sun seeker, you’ll want to stick to southern Italy. If you’re planning a trip to Italy in winter, the weather can be unpredictable, so keep that in mind.

Spring – Spring is a great time to plan your trip to Italy. Prices are still cheaper than in the summer and the weather is usually nice, however, can still be unpredictable with the rainy season. Places in southern Italy will be beautiful and have a more moderate climate. There are quite a few holidays in the spring, so just be aware of that while you’re planning.

Summer – Summer is definitely peak season and the most popular month to plan a trip to Italy. You’ll find the warmest weather and the most crowds during this time. It’s also the most expensive time to visit. If you’re looking for a budget trip to Italy, you may want to avoid the summer season. Something to keep in mind is that in August most Italians go on vacation and the cities shut down to some extent. Many businesses close down for the entire month. The beach towns will be very crowded with locals and tourists alike. Learn more about visiting Italy in August.

Italy in August

Fall – Fall is another great time to plan your trip to Italy. Like the spring you’ll see fewer crowds, but also less rain. As many tourists are back at school and work during the beginning of the fall, it’s generally a good weather time to go and avoid crowds.

Use an Italy Travel Planner

If you need a good way to stay organized while planning your trip to Italy, you can download our free Italy Travel Planner.

Think About What Kind of Trip to Italy You Want & Do Some Inspiration Browsing

Before you really start getting into the nitty-gritty of planning a trip to Italy, consider whey kind of trip you really want to take.

Why are you taking this trip? Is it a vacation where you want to prioritize relaxation? Is it a once-in-a-lifetime trip to Italy where you want to prioritize seeing as much as possible, famous attractions and iconic sites? Do you want to stay in the city center and do a day trip in each location? Do you want to focus on a small group tour or private tours? Is it a romantic trip with your significant other? Is it to connect with your Italian heritage?

Really think about these questions and what the answers are. Spend some time browsing Facebook Groups, Pinterest, and Instagram and exploring ideas and places.

Figure Out Your Budget

After you’ve done the fun part of planning your Italian trip, it’s time to get down to brass tacks and really figure out what kind of trip you can afford. So many people ask us how much a trip to Italy will cost.

This is such a subjective question that it is nearly impossible to answer. When you plan a vacation to Italy, determining factors for the cost of your trip are how flexible your schedule is, what kind of accommodations you prefer, how often you like to eat out, where you want to visit, what kind of transportation you prefer, etc. As you can see, it’s a very personal decision.

Check Logistics for Entering Italy

In your next step in planning a trip to Italy, be sure to check that you can legally enter Italy and that there are no extra steps that need to be taken. Most people living in the USA, Canada, the UK, Australia, and of course, the EU won’t need a visa to visit Italy for up to 90 days. Italy is part of the Schengen Zone, so anyone requiring a Schengen Visa to visit Europe will need to acquire one.

Italy has essentially dropped all other requirements regarding the word which shall not be named, so you’re good in that regard.

Decide Where to Go in Italy

What to visit in Italy is tough to figure out. At this point of your trip planning process, it’s time to decide where you want to go in Italy. This can be one of the most difficult decisions to make while you’re planning a trip to Italy.

Italy is not really that big, but it packs in a whole lot into one relatively small country. Where you go will depend on your preference, budget, time of year, and length of your trip. Besides the most popular cities in Italy, consider visiting some lesser-known places as well. You may want to go all over the country or stick to one or two regions.

Ideas of Where to Travel in Italy

Best Places to Visit in Italy

Hidden Gems in Italy

Most Popular Cities in Italy

Off the Beaten Path Places in Italy

Figure out Your Itinerary

Once you’ve figured out where you want to visit in Italy, it’s time to nail down your specific itinerary. Make sure you’re not overscheduling yourself. Leave plenty of time to wander and relax, even if you’re packing in the destinations. If you’re struggling to pick an Italy itinerary, try looking at these five different Italy itinerary options we’ve created.

Five Itineraries for 10 Days in Italy

Book Your Flights

Once you’ve figured out your itinerary and know where you want to begin and end your trip, it’s time to start looking at flights. We recommend setting a travel alert on your favorite flight search engines like Hopper, Google Flights, Kayak, or Skyscanner. Read more of our tips for finding cheap flights.

You’ll most likely want to fly into one of the major airports in Italy. The most affordable International airports to fly into are usually Rome, Milan, and Venice. If you’re flying into Italy from Europe, you may want to check smaller airports, since budget airlines tend to fly into those more often and at a lower price.

Purchase Travel Insurance

In these uncertain times, it’s never been more crucial to have travel insurance. You just never know. We highly recommend getting it as soon as you book your flights.

Book Your Accommodations

Once your flights are booked and your itinerary is pinned down, it’s time to start booking your accommodations for your trip to Italy. We recommend only booking hotels on official booking sites that offer full refunds, which is almost every hotel these days. But always remember to read the fine print.

I find the best way to search for hotels and apartments in Italy is to use Booking.com. It allows you to search not only hotels, but also home rentals, similar to Airbnb, but better because of the great cancellation policies and customer support that booking offers. Other sites we like to use are Expedia and Hotels.com

You can also check out my accommodation guides for these cities:

Where to Stay in Rome

Where to Stay in Venice

Book Tours and Activities

Once your accommodations are booked, you’ll want to start looking at activities, tours, and cooking classes. My absolute favorite guided cultural tours are run by Walks of Italy. They have great small group tours in all major Italian cities.

If you’re looking for great food tours we also like the 10 Tastings Tours from With Locals. With Locals also offers great history tours, family tours, and welcome-to-the-city tours. Booking tours far in advance is a great way to save money.

Best Tours in Rome

Walks of Italy

With Locals

Package Tours in Italy

If you’re feeling overwhelmed by the tours and options in Italy, you can always book package tours in Italy. These can be a great way to explore areas without stress. If you’re organizing a large group or a family reunion in Italy, these can also be great options if you’re not up for planning a trip to Italy all on your own.

These companies take care of most of the logistics. Just be sure to read recent reviews and have all your questions answered before booking. Always check refund or rescheduling policies. We like to use Get Your Guide and Viator for package tours in Italy.

Get Your Guide Package Tours in Italy

Book Your Transportation

Now that your tours, activities, and classes are booked, you can move on to booking your transportation within Italy. Depending on where you’re going, you’ll need to decide whether you’re going to travel by train, rent a car, or hire a driver. If you’re traveling between major cities in Italy, the rail system will be the best choice. If you’re venturing out of the city center and heading to the countryside, smaller towns, or the coast, you may want to consider renting a car. If you decide to rent a car, be sure to get your International Drivers Permit before you leave for Italy. It’s illegal to drive without it and you may be turned away by your rental car company. It’s cheap and easy to get, so just do it!

How to Train Italy with Confidence

Best Train Ticket Deals

Best Car Rental Deals in Italy

How to Get an International Drivers Permit for Italy

Make a Food Bucket List and Make Dinner Reservations Where Necessary

Italian food! There’s nothing like it! Planning a trip to Italy would not be complete without planning some time and money for food. Italy is full of incredible food. Food should definitely be a part and a highlight of your Italy trip. Take as many food tours and cooking classes as you’re able to fit in and afford. It will make your trip to Italy so much more meaningful and fun! There are hundreds of foods in Italy that we recommend you try.

If you’re eating at any restaurants in the popular cities of Italy, we recommend making as many dinner reservations as possible. You don’t want to schedule every night. Allow room for exploration and spontaneity, but it will alleviate some stress if you can book places ahead.

What to Eat in Italy

What to Eat in Rome

What to Eat in Florence

What to Eat in Venice

How to Find the Best Gelato in Italy

Make a Packing List & Shop for Supplies

Once you’re done with the bulk of your Italy trip planning, it’s time to make a packing list and shop for any items you may need before your trip. What you need will depend largely on the tie of year you take your Italy trip and what season you visit. This Italy packing list will help you find all the things you need.

Italy Packing List

Make Last Minute Preparations

Planning a trip to Italy should be done one year to six months in advance, but there are a few things that need to wait until just before you leave.

Internet Access

If you’re planning to use international data during your trip to Italy, you’ll need to contact your cellular phone provider, plan on purchasing an international SIM card on arrival, or use a portable WiFi Device. We use this one.

Portable WiFi Device

Contact Credit Card Companies

Before you visit Italy, be sure to contact your bank and your credit card company to let them know that you’re traveling abroad. If you’re looking for a great international credit card, we love our Amex Platinum card. It offers so many benefits, including airport lounge access, Global Entry, TSA Pre Check, Airline Credit, Clear, rental car insurance, and more!

Apply for Amex Platinum Card

Sign up for STEP

Before your Italy trip, sign up for STEP (Smart Traveler Enrollment Program). This is run by the State Department and is a free service that allows US Citizens and nationals traveling abroad to enroll their trip with the nearest embassy. This is important if there is a national emergency or if something should happen to you during your trip. You can receive alerts from the nearest embassy, input emergency contact information, and be accessible during an emergency. We have many friends who work at embassies and they agree that this is the most important step (see what we did there?) when planning a trip to Italy.

Plan for Spontaneity

Learning how to plan a trip to Italy is great, but be sure to leave room in your Italy itinerary for fun and spontaneity. Leave time to get lost, make new friends, have fun, and explore Italy like a local. Plan on something going wrong at least once during your trip! We always say “it’s either a good time or a good story.” Hopefully, your Italy trip is both! Happy planning!

I hope this Italy travel planner has been a helpful tool to you and that you’re able to stay organized and plan a trip to Italy efficiently.

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