The Ultimate 2 Week Italy Itinerary: Exploring The Entire Country

Italy is a country that never disappoints and always leaves you wanting more. From Rome to the beautiful city of Venice, here is the ultimate two week Italy Itinerary you need.
Italy Itinerary. Photo: Rebe Adelaida | Unsplash

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Italy is one of those countries that you can visit again and again. No matter if you’ve been ten times, there is always something new to discover. 

The European country has something for everyone, diverse landscapes, breathtaking beaches, ancient history and amazing food. The list goes on! 

So, if you’re planning a trip to Italy, why not spend a few weeks exploring some of the most beautiful places it has to offer? 

If it’s your first time visiting the country, this two-week Italy itinerary exploring the northern regions is exactly what you need. 

The Best Time to Visit Italy 

Italy. Photo: Kristine Tanne | Unsplash

When it comes to planning a two-week trip to Italy, you want to go during a time that’ll suit you, your budget and your preferences. However, some seasons are definitely more convenient than others. 


Like most places, summer is the most popular season in Italy and brings warm weather, sunshine and lots of tourists. 

During the summer, the prices are at their highest, but the beaches are at their best. If you’re hoping to swim and enjoy the sunshine, summer is the best time to visit. 


Winter is the off-season in Italy and brings cold temperatures, rain and grey skies. Due to this, prices are at their lowest, and crowds are as small as they’ll ever get.

Christmas time can bring increased crowds but at the benefit of experiencing Christmas decorations and markets. Rome is the busiest city around Christmas because it is a religious holiday. 

Spring and Autumn

Spring is a great time to visit Italy because the flowers are in bloom and the summer crowds start to disappear. Autumn is the time of year of the olive harvest, where you can taste fresh olive oil. 

The weather during spring and autumn can be unpredictable, with a rainy day here and there. However, the benefit of travelling during these seasons is that the temperature isn’t too hot, the crowds aren’t as bad, and prices are lower.

Days 1, 2 & 3: Rome 

Colosseum, Rome. Photo: David Köhler | Unsplash

The best place to start your holiday in Italy, the beautiful capital of Rome!

Three days in the capital will give you plenty of time to see all the fantastic sights and is a great place to start your two weeks in Italy as the itinerary takes you north. 

Rome is a unique city in itself. Not only is it home to historical landmarks but also an entire country (Vatican City), so you can guarantee there are lots of things to do!

Visiting Rome? The Best Time To Visit Rome To Avoid Crowds

Best things to see and do in Rome 

  1. Tour the Colosseum and Palatine Hill 

If it’s your first trip to the city, strolling through the centre of Ancient Rome will blow your mind. 

A must-do while in Rome is to tour the Colosseum and Palatine Hill, where you can step back in time and learn about the history behind these landmarks. 

  1. Visit Vatican City 

The home of the Catholic Pope, visiting Vatican City is a must while in Rome. 

A country in itself, Vatican City is home to the magnificent Sistine Chapel, St. Peter’s Basilica and St. Peter’s Square. 

  1. Stroll through Centro Storico 

Some of the most iconic landmarks in Rome can be found in Centro Storico. 

Make your way through and make a wish at the famous Trevi Fountain, marvel at the Pantheon and sit on the Spanish Steps. 

After a day of exploring, be sure to indulge in traditional Italian cuisine. Some of the best restaurants in Rome include

  • Felice e Testaccio
  • Trattoria Monti
  • Seu Pizza Illuminati 
  • Pianostrada
  • Roscioli 

Want something different? 14 Unusual Things To Do In Rome

Things to consider in Rome

Like every capital city, Rome does have its downfalls when traveling as a tourist: crowds and heat. 

Being the capital of Italy and one of the most historical in Europe, it’s not hard to believe that millions of people visit Rome every year. 

However, you can beat the crowds and the heat by visiting Rome in the shoulder season (either before or after summer). If you have booked your trip in the middle of summer, there are other ways to combat the crowds. Instead of visiting the famous sights, head off the beaten path, and you’ll be surprised at what you find. 

Days 4, 5 & 6: Florence/Tuscany

Florence. Photo: Ahmed Mansour | Unsplash

The best way to get to Florence from Rome is by catching the 90-minute train. 

Spending three days in Florence and Tuscany is not nearly enough, but it will give you a taste and make you want to go back for more! 

The best way to spend your time in Tuscany is to spend 1.5-2 days in Florence and another visiting a different Tuscan city, either Pisa or Siena. However, if you aren’t too fussed about seeing the Leaning Tower, Siena is a great choice.

Best things to see and do in Florence

  1. Marvel at Renaissance art 

If you’re a fan of art, you must visit the Uffizi Gallery (home to the Birth of Venus) and the Galleria dell’Accademia (home to Michelangelo’s David). 

If you visit during summer, the best thing to do is book skip-the-line tickets to avoid waiting in lines. 

  1. Visit the Duomo di Firenze 

One of the most celebrated cathedrals in the world, you can’t visit Florence without seeing the famous Duomo. 

Located in the centre of the old city, the Duomo stands out, and it’s even more breathtaking up close. While the interior of the cathedral is quite bare in contrast to the exterior, it’s still just as grand and houses magnificent pieces.

  1. Find the best views of the city 

Florence is just as beautiful from a distance as it is up close. Therefore, you can guarantee there are plenty of stunning viewpoints of the city. 

Piazzale Michelangelo and the dome of the Duomo are two of the most popular viewpoints. However, if you want to avoid the crowds, head to the Rose Garden and Palazzo Vecchio. 

If you are planning on taking a day trip to either Pisa or Siena, here are some things to do:

  • See the Leaning Tower of Pisa (Pisa) 
  • Admire the intricate details of the Santa Maria della Spina (Pisa)
  • Check out the Duomo di Siena (Siena)
  • Wander through the Piazza del Campo (Siena)

Tuscany is known for its delectable food, so some of the restaurants you have to dine at in Florence include:

  • La Giostra 
  • Trattoria Marione 
  • Perseus
  • Trattoria Mario 
  • Il Giova 

Things to consider in Tuscany

While three days in Tuscany gives you plenty of choices when it comes to accommodation, the best thing to do is stay in one place. 

Although you may take a day trip to Pisa or Siena, Florence is the best place to base yourself for the three days. 

Days 7, 8 & 9: Cinque Terre

Cinque Terre. Photo: Mike L | Unsplash

No trip (or first trip) to Italy would be complete without visiting Cinque Terre (pronounced cheen-kweh teh-rreh). 

After two days in Rome, depending on your mode of transport, drive or catch the train north to this stunning stretch of coastline. 

Cinque Terre is one of the most unique places in the country, home to jaw-dropping coastal views, beautiful hikes, pretty fishing villages, and delicious food.

Cinque Terre is made up of five towns, all of which are easily connected by train (or ferry during the summer), so no matter which town you stay in, it’s easy to get around.

Best things to see and do in Cinque Terre

  1. Hike between the towns

All five of the towns are connected by hiking trails and offer spectacular views of the coastline. 

Two of the best hikes include the magnificent Blue Path trail between Monterosso al Mare and Vernazza and the trail between Vernazza and Corniglia. 

  1. Watch the sunset in Manarola

Situated in the southern area of Cinque Terre, Manarola is one of the most famous villages in the region due to its picture-perfect view. 

Because of this, Manarola is the best place to watch the sun go down on the horizon. If you can book a restaurant with ocean views, you can watch the sunset with a glass of wine in hand!

  1. Indulge in pesto and seafood 

Pesto is local to the Ligurian coast, meaning it’s a must to indulge in Cinque Terre. 

Also, if you’re a fan of seafood, you’re in luck. The villages of Cinque Terre are all fishing villages and provide fresh seafood to all of the restaurants.

  1. Explore Cinque Terre by boat 

If you want to see Cinque Terre in all its glory, one of the best things to do (especially in summer) is to explore the region by boat. 

Many tour companies take you along the coastline of Cinque Terre to see the breathtaking villages from a different angle. 

If you’re really up for it and have the budget, watching the sunset on a boat is an experience you’ll never forget. 

After a long day of exploring, sit back, relax and try the fresh seafood Cinque Terre has to offer. These are some restaurants you have to try during your stay

  • Fuori Rotta, Riomaggiore
  • Cecio, Corniglia
  • Nessun Dorma, Manarola
  • Gianni Franzi, Vernazza
  • Ciak, Monterosso

Things to consider in Cinque Terre

While bringing a car to Cinque Terre may seem easier to get around, that’s not the case. 

The narrow roads and lack of parking make Cinque Terre a challenge to have a car. Therefore, the best way to travel between towns is by train or hiking. 

However, keep an eye on train and trail closures during your visit. Strikes can happen that shut down the train, and the trails can also be washed out and closed. 

Also, if you’re traveling during the offseason, don’t count on hiking between towns, as the trails are usually closed. 

Days 10 & 11: Milan 

Milan. Photo: Daryan Shamkhali | Unsplash

After spending a few days on the seaside, it’s time to catch the train from Cinque Terre inland to the beautiful Milan. 

The train journey takes three hours, so if you leave early in the morning, you’ll have around 1.5 days in Milan. However, if you really want to visit Lake Como, spend half a day in Milan and a full day in Lake Como. 

As the world’s fashion capital, you can expect the shopping in Milan to be excellent. However, the city’s main attractions are the beautiful buildings and hotels. 

Best things to see and do in Milan 

  1. See the Duomo 

It may seem like every place on this itinerary has a Duomo to visit, but the Milan Duomo is not just another church. It’s the city’s most important landmark that took over 600 years to build. While there is a lot to see inside the cathedral, visiting the top is a must to soak in Milan’s skyline. 

  1. Wander through the Navigli District 

Milan is also known for its great nightlife, and many bars and restaurants can be found in the Navigli District. 

Constructed over hundreds of years with input from da Vinci, Milan’s system of canals gave the city more access to the outside world. 

The Naviglio Grande and Naviglio Pavese are some of the only canals still visible, and around them, bars, restaurants and cafes have popped up. 

  1. Marvel at The Last Supper 

Visiting Milan wouldn’t be complete without seeing The Last Supper painting. 

You would’ve seen magnets, bags and even t-shirts with The Last Supper printed on them, but nothing compares to seeing it up close in the Santa Maria delle Grazie.

  1. Window shop in the Grand Galleria Vittorio Emanuele II 

If you’ve seen any photos of Milan, you would’ve come across one of the Grand Gallery. 

Although it may look like a palace or opera house, it’s actually one of the oldest shopping malls in the world.  

Filled with designer shops such as Prada, Versace and Luis Vuitton, it’s definitely a place to window shop. 

  1. Day trip to Lake Como 

A bucket list destination for many, if you’re staying in Milan, you must take a day trip to Lake Como. 

Less than an hour away by train, the beautiful towns of Bellagio, Varenna and Menaggio are worth spending your time in. 

The best way to get around Lake Como, especially the towns above, is by ferries, which are frequent, allowing you to maximise your time spent in this beautiful part of Italy. 

Much like the shops, there are plenty of restaurants to dine at in Milan, some of the best include 

  • Dongiò
  • 28 Posti 
  • Ristorante Giacomo 
  • Piz 
  • Trattoria Madonnina 

Things to consider in Milan

While Milan is a fabulous city to visit any time of year, if you want to avoid the crowds and sweltering heat, the best time to visit is in autumn or spring. 

As one of the world’s most famous and expensive cities, your trip to Milan won’t be cheap. However, accommodation prices will be more affordable if you visit during the off-season. 

Days 12, 13 & 14: Venice

Venice. Photo: Daniel Corneschi | Unsplash

Finally, your last three days of this two-week trip through Italy will end in Venice. 

With canals, colorful buildings, and gondola rides, there is so much to love about this city in Italy’s north. 

While there is plenty to see and do in Venice if you have good weather while there, a day trip to Murano or Burano is a must!

Best things to see and do in Venice 

  1. Wander through Venice’s Sestieri 

Venice is divided into six districts or Sestieri. And each Sestiere has its own distinct feel. 

San Marco and San Polo are the most popular (and crowded). However, there are plenty of others that are worth seeing. 

Some other Sestieri we recommend worth visiting include Castello, Cannaregio, Dorsoduro and San Croce, where you can get lost in their beautiful, quiet streets. 

  1. Explore the city via the canals 

If there’s one thing you must do while in Venice, it’s to go on a gondola ride through the canals. 

There are plenty of different ways to experience Venice’s canals, depending on your budget. You can go all out and book a private gondola ride, opt for the mid-range shared gondola option or choose the most affordable option and tour the Grand Canal via Vaporetto. 

No matter how you choose to explore the canals, you will be blown away by the views of Venice as you get taken throughout the city. 

  1. Take a day trip to Murano or Burano 

One of the best ways to spend a day in Venice is to venture out and visit one of the nearby islands, Murano or Burano. 

Burano is the most famous of the two and is one of the most colourful islands in the world. Burano is also renowned for its lace, while Murano is known for its glass making.

The only Vaporetto that goes to Burano and Murano is route 12, which departs from Fondamente Nove in northern Venice. 

The best things to do on both islands are to wander through the beautiful streets, indulge in delicious gelato and take in your surroundings. 

Some of the best restaurants to dine at in Venice include:

  • La Zucca
  • Terrazza Danieli 
  • Enoteca Al Volto 
  • Trattoria al Gatto Nero 
  • Al Covo 

Things to consider in Venice 

Venice is one of the most famous cities in the world, attracting 20 million tourists every year. So, if you want to beat the crowds and the heat, avoid going in the summer. However, if you do visit in the summer, be sure to get up early to make the most out of your time there.

The best time of year to visit Venice to avoid crowds, the heat and soaring accommodation prices is spring and autumn. 

How to Get Around Italy 

Transport in Italy. Photo: Josh Hild | Unsplash

Within each destination outlined in this two-week Italy itinerary, the best way to get around is by walking. Walking allows you to go at your own pace and wander streets you wouldn’t if you were to drive or catch public transport. 

However, getting between the destinations on this itinerary requires different modes of transport. 


Catching the train is one of the most popular and efficient ways to get around Italy. However, remember that strikes can sometimes happen and interfere with your plans. 

Booking your train tickets in advance is advised, especially if you’re travelling on high-speed trains, as the prices get higher the closer you get to the date. However, if you’re travelling on regional trains, the prices are fixed so you don’t have to book ahead. 


Renting a car to drive through Italy is popular, but there are a few things to consider. 

Cars are restricted from driving into the historical centres of most cities, including Venice and Florence. There are also towns where there is limited/no parking, making it hard to take a car there. 

With the destinations on this itinerary, the best way to get around is by train. 


Flying in Italy is only beneficial if you travel long distances, such as from Rome to Venice. 

However, with the destinations on this list and the beautiful scenery along the way, the best way to get between destinations is by train. 

The Ultimate 2 Week Italy Itinerary 

Italy Itinerary. Photo: La So | Unsplash

So there you have it, the ultimate two-week Italy itinerary, taking you from Rome north to the beautiful city of Venice. 

If it’s your first time visiting Italy and you want to tick off the most popular places in the country, this itinerary will help you do just that.

As you travel through the northern regions of Italy, you will be blown away by the everchanging landscapes and jaw-dropping sights you’ll see along the way.

From wandering around Vatican City to watching the sunsets in Cinque Terre to gliding along the canals in Venice, there are so many incredible things to see and do on this itinerary. 

Whether you take this trip in spring, summer or autumn, it will definitely be one to remember.


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