The Biggest Mistake People Make When Planning a Trip to Italy (And How to Avoid it)

September 4, 2023

The main problem for anyone planning a trip to Italy is that it’s impossible to see everything you want in one trip! This leads to the biggest travel planning mistake that most people make in Italy – they try to see too many things in too short a time. We hate to be the bearers of bad news, but overloading your itinerary is a recipe for stress.

A woman tourist in Rome takes a photo of the Trevi Fountain during the day with her phone

Are you guilty of trying to see and do everything when you travel?

We understand why you do it and we sympathize, but let us repeat: rushing your Italian vacation is a surefire way to ruin it. Luckily, the solution is easier than you think. Narrow down your focus and divide your time accordingly.

How many days do you need in Italy?

The rhythm of any trip to Italy – that is, how long you spend seeing what you came to see and experiencing what you came to experience – is just as important as what you see and experience. In fact, you could simply book a trip to Rome and spend two weeks hanging out there without ever getting bored. In order to help you get an idea of how to budget your time in some of Italy’s most popular regions, we have created three sample itineraries.

After many years of traveling in Italy and interacting with other travelers, we have honed the rhythm of these itineraries to perfection. Feel free to crib them as is, or use them as a base to create your own custom itinerary. In this case, the where isn’t important; it’s the when that matters.

Two people eating gelato in Italy

Slowing down – and taking time to get to truly savor your destination – will make for a more enjoyable trip. We promise!

The Major Cities Trip

Italy has more major tourist cities than most countries. Of course, the capital is a must, but cities like Florence and Venice are big draws and, honestly, must-sees.

This sample itinerary is perfect for the first-time visitor who wants to “see all of Italy” but can’t choose between regions. It gives a great overview of the most historically significant parts of the country. As a bonus, hitting the highlights on your first trip also help you focus your sightseeing during any return trips to Italy.

Itinerary of Italy’s Major Cities

The Major Cities trip is a great introduction to Italy for those who want to see the most famous art and architecture in the country. It includes the Colosseum, the Duomos of Milan and Florence, and the canals along St. Mark’s Basilica in Venice. To avoid packing in too much, we budget a minimum of two weeks to travel Italy. If you have anything less than that you should take a more leisurely trip (see below).

Two weeks

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

There is no more quintessential Roman experience during your trip to Italy than a stroll around the Colosseum and Palantine Hill.

For anything less than two weeks, you can make the following amendments:

10 days
Cut one city entirely or one day from Rome and one day from Florence. However, don’t cut more than one day from each city!

One week
Cut a city. Rome and Florence have the most to offer the majority of visitors to Italy, so they should probably remain on your itinerary. Choosing between Venice and Milan depends on the time of year and what you are looking for. Venice has more tourism draws like the Doge’s PalaceSt. Mark’s Basilica, the Bridge of Sighs, and of course, all those canals.

However, Venice is packed with tourists in the high season. Milan is not as pretty and has fewer attractions than Venice; however, it’s cheaper, less crowded, and has delicious food. If going in the summer we would recommend Milan. On the other hand, an autumn or winter trip to Italy would have us favoring Venice.

Polenta topped with stewed meat

Trust us – Milan has incredible food. Photo credit: Max Griss

5 days
Choose one of the major cities that you are dying to see and stay there. Seriously, one is enough. even in a city as small as Venice you will have more than enough to keep you occupied as long as you take your time and really immerse yourself.

Vibrantly painted houses along the canal in Burano, Venice

The colorful buildings in Burano are a must-see.

Traveling By Train

Dedicate all of your time to each major city and don’t stray, there’s no time on this Italian travel plan to visit small towns; plan your travel days in advance: you can book high-speed train tickets between cities at TrenItalia or ItaloTreno.

Or, if you think you might feel overwhelmed when navigating the Italian train system, why not opt for easy-to-use ItaliaRail? It provides 24/7 English-speaking customer service, facilitates multiple currency options and allows you to purchase tickets for up to 20 passengers in one booking. Oh, and it has a VIP Lounge in Rome Termini Station! If you have only one week but don’t cut a city, you’re still committing the biggest mistake travelers make in Italy.

The Regional Trip

A regional trip is perfect for those who have already visited the major Italian cities in a previous trip to Italy and want to really take some time in one area to experience it like a local. It’s a great way to fully immerse yourself in Italian culture and avoid the crowded, tourist routes.

Though you can choose any region that interests you, Tuscany is probably the most popular region in which to base yourself. It offers a great mix of history, culture, cuisine, and natural beauty with the added bonus of being close to transport hubs like Rome and Florence. If your Italy trip takes you farther afield you can apply these same time frames to any region but you will need to choose your own destinations.

Rock city of Matera, Italy

Exploring a region means touring the big cities…and then moving past them to soak up the atmosphere of the small towns. Photo credit: Sterlinglanier Lanier

Sample Itinerary

Though you can always base yourself in Florence and see Tuscany with multiple day trips, we’d suggest splitting your stay. Try a few nights in Florence with a day trip to Pisa and a separate day trip to the walled-in city of Lucca. Then, pack your bags and head into the countryside to the red-brick town of Siena. From there, you can take day trips to San Gimignano and nearby Volterra, or south to Montepulciano and Pienza, a UNESCO World Heritage Site. Just don’t forget to try the wine!

Two weeks
Florence: 4 full days. From Florence, take a day trip to Lucca and schedule about a half day for Pisa, with the rest of the day spent in Florence.
Siena: 2 days in the city, with a further 8 days using it as your base to travel to other areas of Tuscany. Make sure not to miss Santa Maria Assunta, Siena’s Duomo and one of our picks for the most fascinating churches in Italy!

From Siena, dedicate day trips to Montepulciano, Pienza, San Gimignano, and Volterra, with a half day dedicated to Monteriggioni. This leaves you with 1 day of extra travel time and one day to return to your favorite town or simply take a well-deserved rest.

Interior of the cathedral or duomo di Siena

Siena’s majestic cathedral dates to the 12th century. Photo credit: Mario La Pergola

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

One week
Cut a day from Florence or cut two of the towns farthest from your accommodation. Take a bit more time to explore the towns you do see.

5 days
Base yourself only in Florence. Take two full days to see the city, then take a day trip to Siena and another to any other city near Florence, such as Pisa, Lucca, or San Gimignano.

Photo By Florian Hirzinger - - Own work, CC BY-SA 4.0,

Pisa is well worth a visit when you’re visiting Tuscany. Photo credit: Florian Hirzinger

Insiders’ tip: A regional trip is all about diving deep into a specific region. Besides Florence, Tuscany’s famous towns and cities tend to be quite small. You can easily visit one town per day, and sometimes even more than one! Your best time saver here is a clear plan about which towns are near to each other and a really good train schedule or GPS.

Logistics in Tuscany

Hilltop town hopping during your day trips means a lot of driving (or bussing it) around countryside, but in beautiful Tuscany that’s an advantage. For starters, you won’t have to lug your suitcases around or waste time checking in and out of various hotels. Also, your base will feel more like home. Instead of staying in a travel hub you might also consider setting up in an agriturismo or a small apartment; it’s a chance to really get to know a region and get a taste of small-town Italy; with regional trains you don’t need to your tickets in advance, but you should read up on the train schedules ahead of time.

Want to experience the best of Tuscany without worrying about logistics and finding your own way around? Our Tuscany day trip from Florence is calling your name. And even if you’re based further afield, no worries—we’ve got you covered with our Quintessential Tuscany trip from Rome.

Planning a trip to Tuscany

There are plenty of beautiful places to explore in Tuscany; the question is, where should you take a day trip from Florence?

The Thematic Trip to Italy

A thematic trip is a unique way for you to connect with your destination. Not only will you see towns that you may not have visited otherwise, but following your theme is sure to create lifelong memories and unique experiences in each place you visit.

The theme is up to you. Perhaps you want to trace the twisted trail of Caravaggio around the country or sample Italy’s best outdoor adventures. One of the most common themes for Italian trips is food. An Epicurean itinerary will not only give travelers a chance to see less-visited regions and understand the customs and peculiarities in Italy’s cuisine, it’s also just delicious!

Pizza in naples during a trip to Italy

Looking for the best pizza in Italy? Get yourself to Naples for their perfect, thin-crust Neopolitan pizza.

Epicurean Itinerary

Though every region in Italy has its own unique cuisine (See: There’s No Such Thing as Italian Food), some lend themselves to tourists better than others. Head to Naples to try traditional Neapolitan pizza and sample their tradition-infused coffee culture. Then go to Rome to explore the beautiful contrast between the city’s love of pork and its delicious kosher traditions in the Jewish quarter. From there, move on to Emilia Romagna, potentially the most famous region for food in all of Italy. After all, its capital city, Bologna, is even nicknamed “The Fat One”! Try the famous ragù sauce on top of fresh tagliatelle pasta or in a traditional, gluttonous lasagna.

Two weeks

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

10 days
Cut one city. Which city depends entirely on your tastes.

One week
Visit just Bologna and Mantua in the north, or Naples and Rome in the south.

5 days
Explore the culinary intricacies – of which there are many – of just one city.

Guests on bologna food tour eating pasta and drinking wine at a restaurant

Bologna is an amazing destination for sampling the most delicious pasta, wine, and charcuterie.

Know Before You Go

If the point is to follow a specific theme, you’ll need to do plenty of research beforehand. We have dozens of food articles for specific destinations on our blog, but search books, blogs and documentaries as well. Don’t forget that unless you are very dedicated you’ll want to see a few things outside your chosen theme, so be sure to budget time for that in each location as well, but don’t stray from the map.

If you want to learn about Italian food with our expert guides, check out our food tours and experiences throughout Italy! Whether you want to explore the markets of Bolognataste the best pizza in Naples or even make your own pasta in Rome, we’ve got a food tour with your name on it.

FAQ: Planning a Trip to Italy

How many days do you need in Rome?

When you plan your trip to Italy, consider no fewer than three days in Rome. As both the ancient and modern capital of Italy, it’s a hub for a lot of things you’re going to want to see. The history, sights, and feel of the city can hardly be seen with less time.

How many days in Venice do you recommend?

It’s possible to see Venice in a day, and many people do it that way. However, uthey miss out on the fantastic nightlife, the feel of Venice with fewer tourists, and the beauty of the city by night.

If you really can’t give it three days, you should at least try staying for one night. Take the next day to visit the Venetian islands of Burano and Murano—our Venice Lagoon Excursion is a fantastic way to experience this fascinating part of the city.

Traveler takes photo of Venice from afar across the lagoons

Venice offers unique and fantastic sights; we recommend spending more than one day here so you can go beyond the center and visit a few of the islands.

I’m planning my first trip to italy – which itinerary do you recommend?

The itineraries above won’t help you see everything in Italy. In fact, if you follow our instruction you’ll actually see less of the country than most, but you’ll enjoy what you do see a lot more. We all want to see everything, but rushing from destination to destination only adds stress and takes away from your overall experience. Don’t worry too much, you’re sure to return. After all, there’s always more to explore!

What other tips do you have for Italy travel planning?

Often – especially when planning a thematic trip – you will want to create an itinerary with smaller cities and lesser-known destinations. However, this also means traveling longer distances.

In order to avoid the big mistake of trying to fit too much in, consolidate your options. You would be surprised how many things there are to try in each place you visit if you just take the time to look. Any Italian will tell you that food should be enjoyed at a leisurely pace and a few meals in a given destination is always better than just one.

Update notice: This article was updated on September 4, 2023. 

The Biggest Mistake People Make When Planning a Trip to Italy (And How to Avoid it)

by Gina Mussio

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