The Perfect Italy Itinerary

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Italy charms and delights its visitors. Each region has its own character and cuisine making deciding where to go on a visit very difficult. From the canals of Venice to the bustling streets of historical Rome, choosing an itinerary for Italy is very challenging.


Luckily, Italy has a great network of trains that help you get from one city center to the next in only a few hours. The trains are cost effective and comfortable and make exploring many regions in Italy in a limited time very easy to do.

Choosing where to go and how long to stay in each place for is difficult for the first time visitor. Use this itinerary for your first visit to Italy to get the most out of your time.

Fly into Rome.

With the largest airport in Italy, Rome is typically the cheapest place to fly into from countries in Europe and around the world. If flights are expensive, try flying into a neighboring European country and booking a cheap budget flight to get you to Italy.

You can easily spend a few days exploring the historical capital of Italy. Wander around the bustling city streets and explore sights like the Colosseum, the Roman Forum, the Pantheon, and the Spanish Steps. Don’t forget to toss a coin and make a wish to channel Lizzie McGuire at the Trevi fountain.

While in Rome, spend a day exploring Vatican City, the world’s smallest country. Within the city you can take tours of the Vatican museum and St Peter’s Basilica which will save you hours in line. Explore the city’s intricate architecture and infamous art including Michelangelo’s famous, Sistine Chapel.


Between Rome and Florence lies Assisi. This UNESCO world heritage city is known for its medieval architecture and for being the birthplace of Saint Francis. Spend a day exploring the sights and wandering the streets.


Approximately 2.5 hours from Assisi, Florence is a great place to stop for a few days. This Renaissance city is located in the heart of Tuscany, one of the most beautiful regions in the world. Spend your days exploring the Duomo, Cathedral of Santa Maria del Fiore, and vast art museums.

This is well known for its traffic so make sure to pencil in extra time to get anywhere. Don’t miss a day trip or two or three to the Tuscany wine region while you’re in Florence.

Cinque Terre

La Spezia is the perfect town to explore Cinque Terre by foot from. It also happens to be a quick 2.5 hour train ride from Florence, so get an early start and you can be exploring Cinque Terre by the afternoon. Cinque Terre or the Five Lands is comprised of the five villages of Riomaggiore, Manarola, Corniglia, Vernazza and Monterosso.

You can tackle the five coastal villages by train or by one of four walking paths. A train pass costs 12 euros and is the time friendly option. You can also do a combo of both if you’re up to exploring by foot for some of it but not all.

On to Milan

A slightly longer train ride pushing 4 hours, the trip to Milan is scenic. Milan is often skipped over for the more historic cities in Italy, but I urge you not to skip it. The Renaissance architecture and unique culture are worth a stop. The fashion capital of the world is home to cathedrals, art museums and plenty of surrounding places for day trips. Head out to visit the Italian Lakes or the Southern Alps after exploring Milan for an afternoon.


Another quick 2-2.5 hour train ride will take you to Venice. The sinking city is what you imagine when you think of Italy. The maze of buildings and canals make walking around the city enchanting. Spend your days exploring the museums, fresh markets and city piazzas. Break for aperol spritz’ and the freshest Adriatic seafood.

Don’t miss a day trip to Murano and Burano island infamously known for their beautifully colored buildings. Both are easily accessible from Venice’s boat taxi network.