One of the most exciting bits of planning  your Italy vacation itinerary is also one of the most important aspects of your trip. The options are, of course, dazzling. Should you go to Venice or Milan? Which cities in Italy are the most important? Which Italian city has the best food? Naturally, we want to see everything that Italy has to offer. However, Italy is more complex than a Renaissance painter’s greatest masterpiece; it reveals more and more of its self with every visit. You simply must return again and again.

This article, written for first-time travelers to Italy, is intended to assist in itinerary planning  for those who want to start in Rome while also wanting to see it all. It is the first in a series of articles which will address a variety of routes throughout Italy and, we hope, prove valuable to travelers with all degrees of familiarity with Italy.

Beginning in Rome is a natural decision. Flights to Rome are usually cheaper than those to other cities in Italy, and Rome is very welcoming to travelers. Signs are often in English and most locals speak English. Rome has more ancient sites than any other city in Italy, and perhaps more than any other city in the world. The Roman Forum, the Coliseum, the Pantheon, and the Circus Maximus are all within walking distance of one another. Because of this, Rome is a good place to become oriented to the culture, language and food. And jet lag, for example, is just plain easier to beat when wandering through the Coliseum.

Rome is a little south of the middle of Italy, so travelers are faced with a decision: travel north or travel south when leaving Rome. The north of Italy has more pizazz: larger and wealthier cities, better-restored ruins, and more organized tourist resources. The south is more rural and quiet. It retains the authentic “old Italy” better than the north, and its natural beauty is sublime. But because there are more important sites to the north, I recommend traveling to Perugia or Florence from Rome.

The most important cities between Rome and Venice are Perugia, Siena, Florence, Bologna, and Verona. The “must-see” cities are Florence and Verona. Travelers with a shorter vacation who also want to fully indulge in each city visited, should focus on (in this order) Rome, Florence, Verona, and Venice. This route is ideal because the travel times between cities are so short that a half a day remains for exploration upon arrival in each of these cities. For example, taking a train from Rome to Florence takes between one-and-a-half and three hours; taking a train from Florence to Verona takes two-and-a-half hours; taking a train from Verona to Venice takes between one-and-a-quarter and two-and-a-quarter hours.

If you have a little more time, simply add another city to your itinerary. Perugia offers a university feel, stunning views, and world-renowned chocolate; Siena’s Piazza del Campo is one of the most beautiful piazzas in Italy; and Bologna’s cuisine is some of the best in Italy.

You might be wondering why I didn’t include Milan on this itinerary. Milan is a modern city and its duomo (a centrally located cathedral) is perhaps the most stunning in all of Italy, but Venice is, well… Venice. Nowhere else on earth will you find townhouses built on top of the sea with gondolas gliding between them. I do not recommend visiting both Milan and Venice unless you have a lot of time. The reason is this: the distance between them is significant enough that it requires a full day of travel. Travelers with a lot of time will find this possible, but those traveling for just ten or so days can better spend their precious vacation hours.

Write in with any questions or comments. I’ll make sure to answer them. Enjoy your planning!

Mattie recently returned to the US after living in Italy for over a year. Read more of Mattie’s posts