Planning a Trip to Italy: 10 Step Easy To Follow Travel Guide

Plan a trip in Italy

Thinking of planning a trip to Italy but don’t know where to start? You’ve come to the right place! Italy is one of the best travel destinations in the world for its epic history, delicious food, and unique culture. With so much to see, trying to plan a trip to Italy can be challenging… Especially if you only have 1-2 weeks! Here are 10 tips for planning a trip in Italy to make all your Europe travel dreams come true!

Italy Travel Inspiration

10 Tips For Planning a Trip in Italy

1. How Long is Your Trip to Italy?

The first thing you need to figure out when planning a trip in Italy is how many days you have. Is this a one-week vacation or do you have an entire month to explore?

The good news is any amount of time you have will work to plan a trip in Italy! With cheap hopper flights and high-speed trains available between cities, it’s easier than ever to get around the country. 

When considering the number of days you have for your trip it’s also important to factor in your travel days. Once you know the exact days you have try to be flexible until you book a flight. We’ll talk more about this part of planning a trip in Italy soon!

Italy Planning a Trip

2. Where do you Want to go?

Like we already mentioned, Italy is a MASSIVE country with so much to see. Depending on how much time you have you may want to focus on one region of Italy. For example, we had less than 2 weeks for our most recent trip to Italy.

For this reason, we chose to plan a trip in Italy for 10 Days through the North of the country. We traveled exclusively by train and were able to see 5 different and incredible cities! This also allowed us a couple of days in each place to fully embrace the culture.

Now don’t restrict yourself to one section of Italy just because it worked out for us. However, keep it in mind if you’re looking for a more relaxing vacation that isn’t go go go every day!

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Planning a Vacation in Italy

3. Pick a Time of Year

You’ll be happy to know that any time of year is a good one to visit Italy! Even in the Winter, there is plenty of fun to be had with Christmas markets and Italian alps skiing adventures. Still, picking the time of year is important for planning a trip to Italy.

It all really depends on what you want to do! We personally love traveling during the swing seasons of Spring and Fall. Not only is the weather cooler during these months but you avoid the touristy summer crowds and prices. Make sure you take all of this into account when doing your own Italy travel planning. 

Italy Seasons Guide

Spring: March-May
Summer: June to August
Fall: September to November
Winter: December to February 

Trip to Italy Vacation

4. Budgeting For Your Trip to Italy

We just mentioned the hefty summer prices so we might as well get into it. How much does planning a trip in Italy actually cost? Of course it depends on how luxurious you travel and what activities you decide to do. Yet, you should know Italy in general is not cheap!  

Aside from traveling in the off-season, some of Italy’s most famous meals like pizza and pasta can be pretty cheap. Also, in cities like Milan you can enjoy the unique Aperitivo tradition for food and drinks. Even in the notoriously expensive city of Venice you can hop around the Cicchetti pubs for under 3 Euros!

Although there are always deals to be had we would never lie… Italy is an expensive place to travel. Make sure you have a decent budget to work with in this part of Europe.

Italy Vacation

5. Plan a Trip in Italy Routes

So what route should you pick when planning a trip to Italy? With mountain villages, beautiful beach towns, and big cities to see, it’s easy to plan an epic and diverse itinerary. Again, it obviously depends on how much time you have in the country and what your interests are.

Are you thirsty for wine tasting in Tuscany or pizza in Naples? How about the castles of Apulia or art museums in Florence? Have fun when creating your itinerary and cater it to the type of traveler you are.

Italy Sample One Week Routes

  • Milan – Bergamo – Verona – Venice
  • Florence  – Cinque Terre – Genoa 
  • Milan – Lake Como – Bologna – Florence 
  • Naples – One Week Amalfi Coast w/ Trip to Capri 
  • Florence – One Week in Tuscany Loop
  • Sicily – One Week Circling the Island   

Planning a Trip Italy Route

6. Book Your Italy Flight

Now for the most expensive part of planning a trip to Italy! The flight can make or break your experience and booking is the first step where things really become real.

If possible, we recommend using a website like Skyscanner to find the best deal. This allows you to search by the date for the cheapest flight instead of just being locked in for specific days.

You should also do your best to get a direct flight to Italy! It’s always worth it to pay a little more instead of dealing with numerous layovers. No one wants to show up for their trip to Italy tired and worn out. 

Verona Italy

7. How to Get Around Italy

There are plenty of great ways to get around the beautiful country of Italy. It has some of the best transportation in Europe which makes it incredibly easy to get from place to place. Take a look at our breakdowns below for each option to decide what works best for you. 

Public Transport: Buses and taxis are readily available throughout the country. 

Rental Car: A car can be a solid way to zip around certain regions of Italy. Just keep in mind, the roads are tight in the mountains and locals may drive faster than you’re used to. Our friends booked with Discover Cars and paid $15 a day to explore Tuscany!

Flights: Flights can be a great option for getting from city to city and are much cheaper than you think domestically. Always give it a quick check before booking trains and buses to maybe save yourself time.

Train: We LOVE the train system in Italy and prefer taking them over most forms of transportation. They’re fast, efficient, and can be cheap if you plan a trip in Italy in advance. 

Plan a Trip to Italy

8. Lock in your Accommodation

Booking your accommodation is another HUGE step when planning a trip to Italy. Luckily, there is everything from luxury hotels to hostels, and home rentals to enjoy during your stay.

Websites like and Agoda are great tools for finding hotels if you’re hopping between cities. For longer stays be sure to check out Vrbo and of course Airbnb for awesome deals on home or apartment rentals.

On a shorter 1-2 week trip we recommend booking all your accommodations in advance. This will save you time when you get there so you can focus on all the fun activities and amazing food in Italy!

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Planning a Trip to Italy Trip

9. Activities in Italy

Onto the most fun part Italy travel planning! What are you most interested in doing and seeing in this amazing country? Tours of all kinds can be found, particularly in the major cities. Museums, walking tours, wine tastings, and food tours are all popular choices.

This is why most people plan a trip in Italy! Taking in the arts, food, and history is all part of the experience. I mean would you really go to Rome without seeing the Colosseum??

In order to not miss out on the best activities, we recommend booking far in advance. The popular tours can go quickly especially in the summertime.

Not one to spend money on touristy stuff? Don’t worry! Some of the most fun times we’ve had in Italy were just strolling the streets exploring, taking in the architecture, and eating! Below are some of our favorite tour ideas when planning a trip to Italy:

What to Do in Venice Italy

10. Pack Your Bags and Go! 

You made it! You’ve booked flights, accommodations, and even some activities for your trip to Italy. All that’s left to do is pack your bags and take off! 

Be prepared, but remember not to overpack. You’re sure to want some souvenirs, fashionable clothes, and Italian leather along your journey.

Need some inspiration for what to pack? Check out our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials!  

5 Quick Steps Before You Leave

  • Confirm your baggage allowance and buy extra before getting to the airport. 
  • Download your airline’s app and check-in for your flight.
  • Send yourself all your travel documents and confirmations in one email for quick access. 
  • If you don’t have a rental car arrange for an airport transfer or set up a taxi or shuttle.

Planning a trip in Italy

Still have questions about how to plan a trip in Italy? How about sharing some of your own Italy travel planning tips? Let us know in the comments below! 

Safe Travels, 
Brigitte & Jake

Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar!

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Italy Trip

Italy Travel Planning 

 Flights: We always check Skyscanner and Kayak to search for cheap flights. That’s how we got from Rome to Venice for under $30 USD!

 Accommodation: Compare multiple sites to get to the best deal such as and Agoda! Also,  Hostelworld should be your go-to source if you’re traveling on a budget. 

Rental Car: We use Discover Cars to explore when traveling. Consider renting a car in one city and dropping it off in another for an epic Italian road trip! 

 Tours: Check out Get Your Guide for thousands of activities around the world. Book a Florence winery tour, Capri Boat trip or street food tour with a local guide in Rome! 

 Travel Insurance: Never travel abroad without protection! We’ve been using SafetyWing for the last few years on the road and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

Italy Travel

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