The Ultimate Guide: 2 Weeks in Italy Itinerary

The Ultimate Guide: 2 Weeks in Italy Itinerary

The Ultimate Guide: 2 Weeks in Italy Itinerary

Are you looking for the best Italy itinerary for 14 days? We’ve put together the perfect 2-week itinerary for Italy, covering all of Italy’s main attractions and some hidden gems. This Italy travel guide will help you plan what to see and do and how to get there.

Two weeks in Italy is not enough to discover the whole country. But you can see the most visited places and at least you’ll have a reason to return to this magical country.

Use our complete Italy itinerary and make the most of your trip.


Italy Itinerary: How to Spend 14 Epic Days in Italy

First, choose where you want to start and end your visit to Italy.

Most people start their Italy itinerary in Rome or Milan. Both cities have international airports, and you can get flights from anywhere in the world to Milan or Rome.

As we traveled to Italy by Flixbus, we started our trip in Milan.

But if you’re arriving by plane, we recommend starting your trip in Rome, as flight tickets to Rome are the cheapest.

Recommended post → Things to Do in Rome

Palatine hill tickets, Rome

Secondly, decide which Italian cities and popular places you want to visit.

This Italy itinerary starts in Milan and ends in Venice, including famous places like Rome, Cinque Terre, Florence, Tuscany, the Amalfi Coast, and some hidden gems.

You can easily follow our itinerary, add more days or reduce the time you spend in Italy.

See also → How to Spend 5 Days in Tuscany

Terme di Saturnia, Tuscany

Some essential Tips for your Italy Itinerary

Buy tickets for tourist attractions and book your accommodation and tours in advance. It is highly recommended in the high season when prices are higher, and tickets sell out quickly.

Remember, if you buy a train ticket from a ticket machine, always validate it before boarding the train!

For this Italy itinerary, travel by car is not recommended. But you should rent a car in Tuscany and a scooter on the Amalfi Coast.

Most cities are walkable and easily accessible by Italian trains.

More about Italy → The Dolomites Road Trip

Florence Cathedral, Italy

How to get Around Italy

There are several ways to get to Italy, such as by plane, car, FlixBus or train.

The major cities have well-connected metro networks, and most cities are walkable.
But you can rent a bike or scooter if you don’t want to walk.

Italy Itinerary by train

The best way to explore Italy is by train. The high-speed Italian trains are fast, comfortable, and cheap.

You can buy tickets at any train station or online. During our time in Italy, we always used the Omio website to check the train schedule and buy tickets.

Read more → Top Things to Do in Venice

Best Gelato in Italy

Italy Itinerary by car

You can also discover Italy by car. But limited and expensive parking spaces, narrow streets, and some parts of the cities not available by car make it difficult to get around Italy.

Italy has many restricted traffic zones (ZTL), and if you drive into them, you have to pay a high fine!

Car rental is essential for exploring the Italian Dolomites and the Tuscan countryside.

You can easily rent a car in major cities or on arrival at the airports. Don’t forget to get travel and car insurance.

Recommended Post → Best Things to Do in Italy

Getting around Italy

Best time to visit Italy

Italy is one of the most visited countries in the world, so try to avoid the peak season, which runs from July to August. During these months, Italy is extremely crowded, tickets sell out quickly, and hotel prices are very high.

The best time to visit Italy is in the spring (March to June) or autumn (September to October), when prices are lower, there are fewer tourists, and the temperatures are pleasant. We did this Italy itinerary in early September.

See also → How to Spend One Day in Capri

One Day in Capri

The Ultimate Italy Itinerary for 2 Weeks

Day 1: Milan

Welcome to Italy! Ciao! We hope you had a great flight and are ready to explore this magical country!

Milan, Italy’s second-largest city, is the perfect place to start your Italy itinerary.

Milan is one of the most underrated places in Italy, and many people skip it from the 14-day Italy itinerary. However, it is one of the places you can’t miss when visiting Italy and is definitely worth a short trip.

Milan is the fashion capital of Italy, a fantastic place with its famous boutiques and beautiful sights.

Recommended Post → Milan Instagram Spots

Duomo di Milano ticket

Milan is located in the Lombardy region of northern Italy. Therefore easily combined with famous cities such as Verona, Lugano, Venice, and the Five towns of the Cinque Terre.

Did you know that one of the most famous works of art in the world, the painting “The Last Supper” by Leonardo da Vinci, is in Milan?

Italy Itinerary in Milan

Find out the best things to do in Milan, how to get around and where to stay.

Read the full post The Perfect Milan Itinerary for 1 Day

Finish your perfect day in Milan with a beautiful sunset and an authentic Italian dinner in the Navigli district.

If you have more time, add an extra day to your Italy itinerary and take a day trip from Milan to Lake Como.

Where to eat in Italy

Day 2-3: Cinque Terre

After one night in Milan, continue your Italy itinerary to Cinque Terre.

La Spezia: Hidden gem on your Italy Itinerary

La Spezia is where most visitors to the Cinque Terre stop as it is only a few minutes train ride from the five villages.

The journey takes around 3-4 hours from Milan to La Spezia, with train tickets starting from 21 EUR.

Discover La Spezia and visit the charming Porto Venere.

Read the full postHow to See Cinque Terre

Castello Doria, Porto Venere

From La Spezia you can quickly reach Porto Venere by bus, the journey takes about 30 minutes.
You can buy tickets at the Tabacchi shops, and a one-way bus ticket costs 3 EUR.

Staying outside Cinque Terre is a budget option, but you can also book accommodation in one of the 5-villages.

We stayed in La Spezia, bought our Cinque Terre Cards that day, and started exploring the villages as early as possible the next morning.

Recommended Post → Cinque Terre: Everything you Need to Know

Italy Road Trip

Five towns

A visit to Cinque Terre, along the Italian Riviera, is a refreshing experience in an Italy itinerary.

There are 5 villages in the Cinque Terre: Monterosso al Mare, Vernazza, Corniglia, Manarola and Riomaggiore.

Its colorful villages, panoramic hiking trails, magnificent sunsets, and fascinating atmosphere attract visitors.

As you can visit the villages in 1 day, Cinque Terre is a popular day trip from Florence, Pisa, or Milan.

Use our Cinque Terre travel guide to make the most of your trip.

Eating pizza in Italy

Day 4-5: Florence

We hope you enjoyed your visit to Cinque Terre. The next stop on our Italy itinerary is the beautiful Florence, the capital of Tuscany.

But before you get to Florence, take a short visit to the Leaning Tower of Pisa.


The train journey from La Spezia to Pisa takes about 1 hour and costs 9 EUR.

The iconic Leaning Tower of Pisa is one of Italy’s most beautiful attractions and should be on every Tuscany itinerary.

Best Day Trip in Italy

The Leaning Tower is located 20-30 minutes from Pisa Central Station. You can spend a few hours or even a whole day in Pisa.

From the top of the Leaning Tower of Pisa, you can see a beautiful view of the city for 18 EUR.

More about Italy → Tuscany Guide

From Florence to Pisa

Depending on when you leave Pisa, you will have plenty of time to visit some of the highlights of Florence. So don’t rush, because the next day you can spend 24 hours exploring Florence.

The journey from Pisa to Florence takes 1-1.5 hours, and the train ticket costs 9 EUR.

More about Italy 2 Days in Florence Itinerary

Piazza della Repubblica, Florence

Capital of Tuscany

If you stay two weeks in Italy, you can’t miss a visit to Florence. Florence is the birthplace of the Renaissance, famous for its architecture and art.

Florence is a perfect base for exploring the Tuscany region and visiting nearby cities.

Statue of David, Florence

It is easy to walk around as most tourist attractions are close to each other.

Stroll through the charming streets of Florence. Visit the Uffizi Gallery, see Michelangelo’s David sculpture, climb to the top of the Duomo and enjoy the sunset at Piazzale Michelangelo.

Recommended Post → Things to Do in Florence

Piazzale Michelangelo sunset, Italy

Day 6-8: Tuscany – Featured destination in the Italy Itinerary

The best part of your Italy itinerary is exploring the Tuscany region.
Start your morning like the Italians, have a coffee with a croissant, then rent a car in Florence.


Take a short trip to Siena, which is 1 hour by car or 1.5 hours by train.

Trains from Florence to Siena run regularly from Santa Maria Novella train station and cost 10 EUR.

Recommended post → 5 Days in Tuscany

Old town of Siena

The historic center of Siena is a UNESCO World Heritage Site and one of the most visited places in Tuscany.

Explore the charming streets of Siena, have lunch in Piazza del Campo and then visit the Fortezza Medicea for a fantastic view of the town.

Good to know that you cannot drive into the center of Siena. You can leave your car in one of the car parks, where you can park for 2 EUR/hour.

See also → Best Places to Visit in Italy

Piazza del Campo, Sienna


After Siena, visit Montepulciano, a 1-hour drive away.
Montepulciano is a charming little town in Val d’Orcia, which was our base in Tuscany.

One of the best things to do in Italy is wine tours, and a trip to Tuscany is not complete without tasting some of the famous wines.

The best cellar in Montepulciano at Cantina Ercolani is well worth a wine tour. Here you can visit the underground wine cellars and taste the famous Tuscan wines.

Discover the Montepulciano and stroll around its narrow streets.

Italy food tour itinerary

Tuscan countryside

Tuscany offers a unique experience and a scenic road trip. A place where tourists come from all over the world to discover the famous Tuscany countryside.

The best way to explore Tuscany is by car.

Enjoy panoramic views of cypress-lined hills, taste the best wines, visit Renaissance towns and watch the most beautiful sunrise at the Terme di Saturnia.

Agriturismo Baccoleno

We spent 5-days in Tuscany, which was enough time for our first visit. However, if you have more time, add an extra day to your itinerary in Italy and visit San Gimignano and Greve in Chianti.

Keep reading → Places to Visit in the Dolomites

Wine tasting in Tuscany

It’s time to say goodbye to beautiful Tuscany and continue your Italy itinerary to Rome or the Amalfi Coast.
We drove back to Florence to return the rental car and buy some more souvenirs.

We traveled from Florence to Rome, which was about 3.5 hours by train and tickets start at 22 EUR. The faster trains are more expensive but if you have limited time it is worth paying more.

Best Places in Tuscany

Day 9-10: Rome

The capital of Italy, also known as the Eternal City, is the highlight of every Italy itinerary.

Did you know that one of the seven wonders of the modern world is the Colosseum, located in Rome?

The best part of the Italy itinerary is trying the heavenly Italian food. Go to the Trastevere district where you’ll find the best restaurant in Rome, Carlo Menta. Be sure to try the pizzas, pasta, tiramisu, and gelato.

Explore the historic city of Rome, visit the famous Colosseum, make a wish at the Trevi Fountain and take a day trip to the Vatican City.

Colosseum Rome, Italy

Vatican City

In the heart of Rome is Vatican City, the smallest country in the world. You can travel by metro to Ottaviano station and then walk a few minutes to reach Vatican City.

Tickets cost just 1.50 EUR for one-way and travel time is around 20-30 minutes.

You can visit St. Peter’s Basilica and Square, the Vatican Museums, and the Sistine Chapel.

Read the full post → Rome Guide

How to visit Vatican

Day 11-13: Amalfi Coast

The Amalfi Coast is one of the most beautiful coastal regions in the world. From Rome, Milan, or Florence to Naples, you will arrive at Napoli Centrale by fast train and have several options to get to Sorrento.

The easiest and cheapest way to get from Naples to Sorrento is to take the Circumvesuviana train, which takes around 1.5 hours, and the ticket price is 4 EUR.

Once you arrive, take a stroll around the charming town of Sorrento, try the famous limoncello, have dinner and then watch the beautiful sunset.

Amalfi Coast towns


Sorrento is not part of the Amalfi Coast. However, many people stay in Sorrento and then take a day trip from here to Capri.

From the port of Sorrento, you can easily take the public ferry, which costs 19.50 EUR for one-way and takes about 30 minutes. One day in Capri is perfect for exploring the main attractions and a boat trip around the island of Capri.

Read the full post → One Day in Capri

Capri boat tour


Good morning! After breakfast, it’s time to set off on one of your best discovery trips. 
Start the morning with a Vespa adventure and visit Positano, the most picturesque town on the Amalfi Coast.

The journey time by scooter between Sorrento and Positano is 30 minutes.

In Positano, you can’t miss the Spiaggia Grande beach, as it is the most photographed spot on the Amalfi Coast. 

After Positano it is worth visiting the other Amalfi Coast towns such as Furore, Ravello, Atrani and Amalfi.

See also → Positano

Amalfi Coast, Italy

Day 14: Venice

Venice is one of Italy’s most romantic cities and a must-see when visiting Italy. It is easy to get around Venice, and there is so much to see in one day.

Venice is a unique destination and the perfect place to end a trip to Italy. Spend your day walking along the canals or crossing the bridges and enjoy the beautiful sunset.

Venice has good public transport connections to the nearby countries and has an international airport.

The next day, say goodbye to Italy and fly home or visit the Dolomites.

Read more → Things to Do in Venice

How to visit Venice, Italy


If you have more time, the Dolomites are well worth a visit on your Italy itinerary. You can easily rent a car in Venice and spend a few magical days exploring the Dolomites.

Good to know
You can easily modify our Italy Itinerary to extend or reduce the days. Most people take a 7 or 14 days Italy Itinerary on their first visit.

Recommended Post → Dolomites Road Trip

Lago di Braies, Dolomites

The Italian Dolomites are one of the most beautiful places in Italy and the most stunning mountain destination in the world.

In the Dolomites, you can visit some fantastic places like the Tre Cime di Lavaredo, Seceda, Lago di Braies, and Alpe di Siusi.

See also → Best Day Hikes in the Dolomites

Tre Cime di Lavaredo

We hope our Italy itinerary will help you plan your next trip, and for more tips, check out all of our Italy travel blogs.


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