Italy by Rail – A Complete 3 Week Itinerary

In Italy it is always so much to see, so little time. With impressive cities, endless history, fantastic cuisine and friendly locals, no time is ever enough in Italy. People always ask me “Where should I go in Italy?” to which I can honestly respond “Everywhere!” Yes, the country really is that spectacular and there is so much to see. So if you’re planning your first trip to Italy and want to hit up all the highlights; here they are…

italy by rail Milan Dom


Start your Italian journey in Milan, the financial centre of Italy and a busting metropolis filled with fashion, arts, and great cuisine (though you’ll find the latter everywhere in Italy!) You only really need one night in Milan to get over the jet lag, as well as seeing the impressive Milan Cathedral (probably the most impressive in all of Europe), Leonardo Da Vinci’s last supper mural and Galleria Vittorio Emanuele II.

Stay: 1 night

Read more: What not to miss in Milan

Torno Italy | Lake Como

Lake Como

On your second day catch the train to Como and begin exploring the Italian lakes district. Lake Como is arguably the most picturesque of all, so pick yourself a town to be based in and prepare for a world of expensive villas, impressive gardens, and casual afternoons on the public ferry service back to your abode.

Stay: 2 nights

Read more: A Quick Guide to Lake Como



Ahhhh Venice, how could you go wrong!? You’ll need precisely two nights to see the highlights of Venice, wander the streets, ride along the canals and make a quick escape to a quieter stop afterwards so as to escape the crowds.

Stay: 2 nights

Read more: A Quick Guide to Venice // Postcards from Venice



Verona is the perfect stop after Venice simply because it is smaller, less busy, and just as magical with the added glorification of a link to Shakespeare. One night will give you just enough time to wander the streets and indulge in some street sweet treats.

Stay: 1 night

Read more: One day in Verona

Bolonga via Expedia

Image via


If the name sounds familiar, you’re probably thinking of bolognese. And yes, Bologna is the birthplace of bolognese. Stop in at Bologna for just a few hours to eat the dish in its hometown and climb the tower for a great view over the city.

Stay: Day Trip

Cinque Terre, Italy

Cinque Terre

Onwards to Cinque Terre, the gorgeous coastal area of cliffside towns, and plenty of them! You will need to transfer to a bus in order to make the full journey, as Cinque Terre itself is not connected to a train line. This region is a great excuse to wander without rhyme or reason, with your hardest choice for the day being which gelato flavour to indulge in!

Stay: 3 nights

Read more: Cinque Terre Guide



And now for my favourite city in Italy; Florence. This would have to be one of my favourite places in the whole world, especially in the summer sunshine. There’s plenty to see and do in the city itself, but you’ll need to reserve one full day for a Tuscany vineyard experience out of town. Ahhh how I miss Firenze!

Stay: 4 nights

Read more: You Can’t go to Florence & Not see these 20 Attractions

Me at seventeen (ha!)

Me at seventeen (ha!)


On one of your afternoons in Florence, catch the train onwards to nearby Pisa to see the sight in which this town is made famous for: the leaning tower of Pisa. The food is much cheaper here than in Florence, so perhaps make it a lunch stopover and you’ve got a win-win!

Stay: Day Trip

Rome if you want to


Rome, the eternal city. There really isn’t a city in the world quite like Rome and no other city has ever had the power to make me feel so young and so small. The city is ancient, overbearing, and at times overhwelming. But you absolutely cannot cut yourself short on time here – there is just so much to see and do!

Stay: 4 nights

Read more: Rome Bucket List

Where to find the Best Pizza in Naples


Onwards to the Amalfi Coast with your first stop being Naples, the birthplace of pizza! Leave your bags at the train station and make a run for the best pizza in town. Trust me when I say this stop is entirely worth it just for the pizza alone!

Stay: Day Trip

Read more: Where to find the Best Pizza in Naples

Pompeii via Business Insider

Image via Business Insider


Another great day trip during your time in the Campania region is to wander through the ruins of Pompeii. This is a magnificent insight into the history of the country and will leave you awestruck long past the day you fly home.

Stay: Day Trip

Le Sirenuse Positano

Amalfi Coast

Last but certainly not least, the stunning Amalfi Coast! This is for sure my favourite area in Italy to stop, unwind, and soak up that Italian sunshine. Be sure to spend a couple of nights in Sorrento, take a day trip to Capri, spend a further two nights in Positano and make a further day trip to both Amalfi & Ravello.

Stay: 4 nights

Read more: A Quick Guide to Positano

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    May 25, 2016 at 8:20 am

    I’m so glad you put the Cinque Terre on this list. I visited just last weekend. But you can’t actually catch a bus between the towns. They are only accessible by ferry when it is good weather, by hiking, or by the most easiest method which is the train that runs between all of them from La Spezia to Levanto. They arrive every half an hour which makes it super easy to visit. In my opinion its more beautiful than the Amalfi- one of my favourite places in Italy. But Florence is also great (I’ve been living here for two months and I’m so sad to say goodbye to it this weekend). There are so many cheap food options; go to the Central Mercado- on the top floor there is a food court with amazing and cheap pizza and pasta. Go to All Antico Vinioa where you’ll find huge and amazing panini for 5 euros, and go to Kitsch Devx for Aperitivo- you pay 10 euros for a cocktail and access to the all you can eat buffet that includes delicious pizza and pasta and other goodies.

    Megan Indoe
    May 17, 2016 at 4:59 pm

    I love the places you chose to visit on your trip! I feel like no matter how long you spend in Italy it just isn’t enough time! I stayed for 4 months and never made it to the south or Pompeii. I am dying to go back! Thanks for sharing!

    May 17, 2016 at 9:06 am

    Brilliant, thank you so much for sharing! I’ve only been to Italy once, two nights in Milan, but I loved it – would love to visit Venice and the Amalfi Coast looks just gorgeous!

    May 17, 2016 at 8:08 am

    I love this and such a good, well-rounded itinerary! You need that amount of time to fully enjoy Italy 🙂 Xo, Chloe

    Ellé Simpson
    May 17, 2016 at 7:21 am

    I love this post! I’m desperate to go to Italy and travel, it looks so beautiful!

    Ellé |

    May 16, 2016 at 6:25 pm

    Oh wow this is my dream trip! And that pizza in Naples looks soo good – it instantly made me hungry 🙂 Looks like you had a fab time. I need to do this soon!!

    Holly at

    Rob Conroy
    May 15, 2016 at 1:53 am

    Great post Brooke! I’ll definitely be taking your recommendations when I next visit Italy!

    May 14, 2016 at 5:49 am

    Your trip in Italy has so many similarities with mine. Then again I wish I had this guide then to give me and my friend some advises for our trip. We too well in love with Florence. And even now, year and half later I still sometimes go back to those times in Tuscany sun and views of the city it self. So for anyone going to Italy; put Florence on your stop-list! I still wish to see Venice and Verona. And I’m sure there is still countless little cities by the sea to see. But you gotta have some dreams left, right? 🙂 Loved your post.

    Tabitha Faith
    May 13, 2016 at 4:22 am

    I am sooo jealous! This is definitely the trip I’m taking next summer, no matter what!

    May 13, 2016 at 1:35 am

    I love Italy!! So beautiful…

    May 12, 2016 at 4:25 pm


    May 12, 2016 at 2:54 pm

    I love traveling via train! I’ll be in Italy for a bit over a week in October! Saving this guide for my trip.


    May 12, 2016 at 9:20 am

    Looks so wonderful! I haven’t been to Italy since 2009!! Always ready to go back☺️

    Amanda @ Positively Amanda
    May 12, 2016 at 5:19 am

    AH! italy looks incredible!

    May 12, 2016 at 2:16 am

    This is wonderful! I’ve also wanted to do a full tour of Italy and this lays it out perfectly. Thank you, thank you!

    May 12, 2016 at 1:22 am

    Hi! Great itinerary! I am visiting italy in a few days and made a really similar itinerary adding some small tuscany towns. Thanks for the information, now i know i am on the right way!

    May 11, 2016 at 9:56 pm

    Hey Brooke,
    Sorry, I must correct you about Cinque Terre. I’m currently travelling through Italy and spent a fair bit of time there. Each coastal town does have a train station, which makes it easy to get to the area – we travelled to Monterosso from Stresa via Milan. It is also is a cheaper way of travelling between the towns if you can’t make the trek or fork out the cash for the ferry.

    harry hepden
    May 11, 2016 at 4:54 pm

    So far I’ve got Florence and pisa (Rome and Naples in the summer) Ticked of my italian bucket list

    Saakshi Kumar
    May 11, 2016 at 1:33 pm

    This is simply a well-potted post about Italy’s itinerary. Thank you so much. 🙂

    the adventurer
    May 11, 2016 at 12:38 pm

    Wow! Great itinerary for Italy! I have traveled to Italy several times but usually one city at a time and have been wanting to take a trip where I travel through the whole country =o)

    May 11, 2016 at 7:30 am

    Ahhh i miss inter railing Italy so much! I wish i’d visited pompeii and naples but theres always time for another trip haha.
    Also Sicily is an amazing place to add on too! So many places to go to there alone!

    May 11, 2016 at 7:26 am

    Dear Brooke, Thank you for this valuable information. I am planning a trip to Italy, and starting north and going south is a good idea. Which rail line do you recommend? Brunie from Oceanside.