Planning Your First Trip to Italy: A Traveler’s Guide

Nothing compares to planning your first trip to Italy.

Just looking at a map, it can be hard to get a good grasp on just how big Italy is, especially if you're from further away, like the States.

Italy is about 600 miles long (1000 km or so) from top to bottom, and each region (and city) has something different to offer.

So many factors go into planning your first trip to Italy, like:

• How much time you have.
• The time of year.
• What's important to you.
• Your budget.
• Your future travel plans.

Somewhere within the mix of all of those lies the perfect blend for your journey abroad.

In this guide, we're going to take a look at all of these and how they play a part in planning a perfect trip to Italy!

Questions you need to ask yourself

Planning a trip to Italy is much like planning a trip anywhere else. There are tickets to think about, where to go, hotels, and what to do... There's definitely prep work involved.

For your first time in Italy, answering the following questions in the following order will help you narrow down your options to start really getting into the weeds of planning.

1. How much time do you have?

Is it a long weekend? A week? More? The amount of time you're able to allocate to your trip will make a huge difference in how you go about planning.

This will affect how many cities you can see, hotel options, sightseeing, etc.

If you nail down how long you have first, the rest will begin to fall into place.

2. Is your heart set on anything?

Is there anything you 100% want to see or do without a doubt? Is a canal ride in Venice at the top of your Bucket list? Or maybe you've always wanted to see Da Vinci's Last Supper in Milan. If there's something your heart is set on seeing or experiencing, make a note of it.

In the same vein, maybe you're not set on seeing a specific monument, city, or work of art. Perhaps, instead, you're interested in a specific vibe, such as museums and cobblestone streets or sandy beaches and aperol spritzes. If you like to travel a specific way or want a certain feeling from your vacation, this is something to consider.

3. What time of year will you be traveling?

If you already know what time of year you can travel (because you have days off of work, for example), make a note of it. Traveling in winter, for example, might present different opportunities than traveling in summer.

Your schedule may allow you to plan a trip at any time of the year. This will give you more flexibility (and control) over the experience you want to have - whether that's a snowy one or a sunny one!

4. What's your budget?

It's not everyone's favorite topic when planning a trip, but it is one of the most important ones.

Are you strictly tied to a budget? Are you looking for the cheapest options, or do you have more wiggle room?

Budget is a huge part of planning your first trip to Italy as it's going to dictate (more or less) what you're able to see and do. Are private tours on the table? What about remote destinations with high costs?

If you haven't mapped out a specific budget, at the very least, you should know whether you are working with a very limited budget, a high one, or somewhere in between.

5. How do you like to travel?

Do you like a tightly defined schedule? Or do you prefer to open your window and see where the day takes you?

Whether or not you want to have a daily agenda, a vague idea of the day, or just to fly by the seat of your pants, your travel style will affect your planning.

If you're a self-proclaimed Type-A traveler, you've got some notebooks and multi-colored pens to buy. If you're the latter? Some casual reading about local landmarks and sights may be enough for you.

If it's your first big trip in general, you might not be sure which appeals to you. In that case, a happy medium is probably your best bet.

6. What does the future of travel look like for you?

This is one of the most forgotten questions that travelers need to ask themselves when planning a trip.

Are you ever planning to visit Italy again? Or is this a once-in-a-lifetime trip for you? Knowing whether or not you plan to visit again will help you prioritize the things you want to do and see.

Who knows where it all will take you? After all, life works in mysterious ways. Still, this is an important thing to consider for your very first trip.

How to plan your first trip to Italy

Once you've answered all of those questions and have a good grasp of how much time you have, how flexible your cash flow is, etc., you can start to put the pieces together.

First and foremost, if your heart is set on a city, landmark, or monument, that is an excellent starting point.

Let's take the example above, with an imagined set of answers to the questions:

• You're a traveler whose heart is set on a Venice canal ride.
• You have a total of 10 days, but that includes travel days (flights).
• You have some flexibility with your schedule, but the end June is really the best time for you.
• You want to be as frugal as possible, but you also don't want to skimp on experiences.
• Because... This may be the only time you visit Italy! You want to see as many places in the world as possible, so you're not sure you will have the opportunity to come back.
• You want some general plans but don't want to be tied to a formal schedule because you do enjoy some spontaneity.

With this example, you can see how much easier it makes it to plan a trip! With just this information, this traveler can start to look at Venice as a hub.

• What's the best way to get to Venice from where you live?
• What are some good day trips out of Venice, or even a multi-day trip?
• With flexibility in your schedule and wanting to stay frugal, are tickets cheaper at another time of the year?
• Because this may be your only time in Italy, and your heart is set on a Venice canal cruise, make sure you book tickets for this in advance (if possible).

Expert tips for planning your first trip to Italy

• Have flexibility. Try to prioritize a few things at most, then be flexible about the rest of your trip and what experiences you can have.
• Don't pack too many activities into your trip. A common mistake for travelers is to pack back-to-back tours, excursions, museum trips, etc. Usually it's because travelers want to make the most of the time spent abroad. Who doesn't? But this sort of planning usually backfires.
  Try not to pack too many things into each day. Slow down. Enjoy the atmosphere. You're going to likely be jetlagged, walking a lot, and in an entirely new atmosphere. Give yourself a little time and don't "see everything" just for the sake of "seeing everything".
• Make sure you understand the entry requirements. Some travelers need a visa to visit Italy. Others need ETIAS (once it has been launched at the end of 2026). If you're getting a Schengen visa for your trip, remember that visa travel insurance is mandatory.
• The summer months are the peak of tourist season for all parts of Italy. Keep in mind that prices can be higher, tours and museum tickets can sell out, and there are more crowds.
• Buy tickets/make reservations in advance. If you want to go to a specific museum or eat at a certain restaurant, book your tickets or make reservations in advance - especially during peak tourist season.