What is the Biggest Mistake When Traveling to Italy? (And How to Avoid It)

It’s impossible to see everything in one trip, which is the main problem for anyone who plans a trip to Italy. This is the biggest mistake people make when planning a trip to Italy. They try to see too much in too little time. Although we don’t like to hear bad news, overloading your itinerary can lead to stress.

We get why you do it, and we understand your frustration. But let’s be clear: Rushing your Italian vacation can lead to disaster. The solution is simpler than you might think. You can narrow your focus and split your time accordingly.

It is as important as the things you see and do is how you experience them. You could easily book a Rome trip and then spend two weeks there, without getting bored. We have created three sample itineraries to give you an idea of how to budget time in the most popular areas of Italy.

We have perfected these itineraries over many years of travel in Italy and interacted with other travelers. These itineraries can be adapted to your liking, or used as a starting point for creating your own itinerary. The where is irrelevant in this instance. It’s the how that’s important. We’ll be available in the comments section for any questions.

The Major Cities Trip

Italy is home to more tourist destinations than any other country. The capital is essential, but major tourist cities such as Florence and Venice can be a real draw and must-sees. This itinerary is ideal for a first-time visitor to Italy who doesn’t want to choose between the different regions. This sample itinerary gives you a good overview of the most historical parts of Italy. It will help you plan your next itineraries to Italy.

Sample Itinerary:

For those who are interested in seeing the best art and architecture of Italy, the Major Cities trip is an excellent introduction to the country. It includes the Colosseum and Duomos of Milan, Florence, as well as the canals that run along St. It includes the Colosseum, Duomos of Milan and Florence, as well as Venice’s canals. We recommend that you travel to Italy for no less than two weeks in order to avoid overpacking. You should travel more leisurely if you have less than that. (See below ).


Two weeks

  • Rome: 4 Days
  • Florence: 3 Days
  • Venice: 3 Days
  • Milan: 4 days

You can make the following changes for less than 2 weeks:

10 days:

You can either cut one city completely or leave Rome for one day and Florence for one day. However, don’t take more than one day out of each city.

One Week:

You can cut a city. Rome and Florence are the best places to visit in Italy, so you should keep them on your list. It depends on what time of the year you are choosing between Venice or Milan. Venice is home to more tourist attractions like St. The Bridge of Sighs, St. Mark’s Basilica and the Bridge of Sighs are just a few of the many tourist attractions in Venice. It is however packed with tourists during high season. Milan is less beautiful and offers fewer attractions, but it is cheaper, more crowded and offers better food. We recommend Milan if you are visiting in the summer. We would recommend Venice for a winter or autumn trip to Italy.

5 days:

Stay in the city you love. One is sufficient. Even in a small city like Venice, you’ll find plenty to keep you busy as long as your take your time and immerse yourself.

Insiders’ tips:

It is important to spend at least three days in Rome when planning your trip to Italy. It’s both the modern and ancient capital of Italy. You’ll want to see many things. It is impossible to see the history, sights, and feel of the city without spending some time.

Venice can be visited on a single day. Many people do so, but they miss out the amazing nightlife, Venice’s feel with fewer tourists and the beautiful city at night. You don’t have to stay for three days if you aren’t able to. The next day, take a trip to the Venetian islands Burano or Murano.

Learn Before You Go:

You should dedicate your time to each city. Don’t waste your time visiting small towns. If you are worried about the complexity of the Italian train system, you can opt for the ItaliaRail. You can book tickets for up 20 passengers with one booking and receive English-speaking customer support 24/7. It also has a VIP Lounge at Rome Termini Station. You still make the most common mistake when you travel in Italy if you only have one week.

Our guide to travelling by train in Italy provides more information on how to get from one place to the next.

The Regional Trip

If you have been to the main Italian cities on a previous trip, and wish to spend some time in another area of Italy to truly experience it as a local, a regional trip is the best option. This is a great way for you to immerse yourself into Italian culture without having to travel on tourist roads. You can base yourself in any region you like, but Tuscany is the most preferred. It is close to major transport hubs such as Rome and Florence, and offers a wonderful mix of history and culture. You can use these time frames for Italy trips that take you further afield, but you will need your own destinations.

Sample Itinerary:

Although you can always base yourself at Florence and take multiple day trips to Tuscany, we recommend splitting your stay. You can spend a few nights in Florence and take a day trip into Pisa or Lucca. You can then pack your bags and travel into the countryside to the red-brick city of Siena. You can then take day trips to San Gimignano or nearby Volterra, as well as south to Montepulciano, a UNESCO World Heritage Site. Don’t forget the wine!

Two weeks

Florence: 4 full days. Take a day trip from Florence to Lucca, and spend the remainder of the day in Florence.

Siena: Two days in the city and an additional 8 days to use it as your base for travel to other parts of Tuscany. Day trips from Siena to Montepulciano and Pienza, San Gimignano, San Gimignano, Volterra, and Monteriggioni are possible.

You have 1 day more travel time, and you can return to your favorite place or take a well-deserved break.

10 days:

Combine San Gimignano and Volterra and/or Montepulciano and Pienza.

One Week:

You can either cut a day off Florence or go to two towns that are far from your accommodation. You may want to spend a little more time exploring the towns that you see.

5 days:

Only base yourself in Florence. Allow yourself to explore Florence for 2 days. Then, take a day trip from Florence to Siena or to San Gimignano.

Insiders’ Tip A regional trip involves diving into a particular region. The most famous Tuscan cities and towns are not located in Tuscany. One town can be visited per day. Sometimes, you may even want to visit more than one. A clear plan of which towns are close to one another and a good GPS or train schedule is the best way to save time.

Check out our articles about the top Tuscany towns, round one, and around two.

Learn Before You Go:

You will need to drive or bus it around the countryside while hilltop town-hopping. But in Tuscany, that’s a plus. You won’t need to carry your luggage around and waste time checking into different hotels. Your base will feel like a home. You might consider renting an apartment or agriturismo instead of staying in a major travel hub. It’s a great way to get to know the region and experience small-town Italy. Regional trains are available, so you don’t have to book your tickets ahead of time.

The Thematic Trip

It is an unique way to get to know your destination through a thematic trip to Italy. You will not only see new towns, but you’ll also have unique experiences and lifelong memories in every place you visit.

You can choose the theme. You might want to follow the Caravaggio trail around Italy, or enjoy the best outdoor adventures in Italy. Food is a common theme on italy trips. Epicurean will allow travelers to explore less-visited areas and learn about the peculiarities and customs of Italian cuisine. It’s also delicious!

Continue reading 6 Reasons Fall is the Best Season to Visit Rome

Sample Epicurean Itinerary:

Each region of Italy is unique, and each one has its own cuisine. (See: There’s no such thing as Italian Food). However, some regions are more welcoming to tourists than others. Visit Naples to enjoy traditional Neapolitan Pizza and their coffee culture. Next, visit Rome to see the stunning contrast between Rome’s love for pork and its wonderful kosher tradition in the Jewish Quarter. You can then move on to Emilia Romagna which is possibly the most well-known region in Italy for its food. Bologna, the capital of the region, is often called “The Fat One”. The famous ragu sauce can be used on fresh tagliatelle pasta, or as a traditional, rich lasagna. Mantua is located in the heart of northern Rice Country and was chosen as the Cultural Capital of Italy for 2016 and the European Capital of Gastronomy 2017.


Two weeks

  • Naples: 3 Days
  • Rome: 4
  • Bologna: 3 Days
  • Mantua: 3
  • 1 day extra travel time

10 days:

Reduce one city. It all depends on your taste.

One Week:

Bologna, Mantua and Naples in the north are the best options. Rome and Naples in the south are the best.

5 days:

Explore the culinary intricacies of a single city.

Insiders’ Tip:

You can travel longer distances with your thematic journey, but you can visit smaller cities or lesser-known places. To avoid making the “big mistake” by trying to fit too many things in, you should consolidate your choices. Every Italian will tell you that it is better to eat at a slower pace than to eat just one meal in a destination. If you take the time to explore, you’d be amazed at how many different things you can try in every place you visit.

Learn Before You Go:

You will need to do extensive research if you want to stick to a particular theme. There are many food articles that can be found for specific destinations on our blog. You can also search blogs, books and documentaries. You may want to see some things that are not within your chosen theme unless you are extremely dedicated. So budget time to visit each location, but stay on the map.

Our Rome Food Tour and Venice Food Tour will teach you all about Italian cuisine.

These itineraries won’t take you to all of Italy. You’ll see more of Italy if you follow our instructions, but you’ll still enjoy the places you see. It’s human nature to want to see all of the places, but hurrying from one place to another only increases stress and detracts from the overall experience. You’ll be back, so don’t worry! There’s always more!