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

April 13, 2016

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.

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.

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 written 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. As always, we’ll be waiting in the comments sections for anyone with questions.

There is no more quintessential Roman experience during your trip to Italy than a dawn visit to the Spanish Steps.
There is no more quintessential Roman experience during your trip to Italy than a dawn visit to the Spanish Steps.

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 zones. It gives a great overview of the most historically significant parts of the country. As a bonus, it will also help you plan where to focus your sightseeing during your return trip to Italy.

Sample Itinerary:
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

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. But 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, it is also packed with tourists in the high season. Milan is not as pretty and has fewer attractions but it’s cheaper, less crowded, and has better 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.

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.

Insiders’ tips:
When you plan your trip to Italy, consider no fewer than 3 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.

Venice can be visited in a day trip, and many people do it that way, but they 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.

Know Before You Go:
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 by 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.

For more on getting from one city to another check out our guide to traveling by train in Italy.

Tuscany
Exploring a region means touring the big cities…and then moving past them to soak up the atmosphere of the small towns.

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.

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. 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.

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 2 full days to see the city, then take a day trip to Siena and another to any other city on the list near Florence, such as Pisa, Lucca or San Gimignano.

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.

Explore possible destinations with our articles on the top towns of Tuscany, round one and round two.

Know Before You Go:
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.

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

The Thematic Trip

A thematic trip to Italy 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!

Read More: 6 Reasons Why Fall is the Best Time to Visit Rome

Sample 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. Finally, Mantua, in the heart of northern rice country, was named Italy’s Cultural Capital for 2016 and the European Capital of Gastronomy for 2017!

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.

Insiders’ Tip:
Your thematic journey can lead you to smaller cities and lesser-known destinations but it can also see you traveling longer distances. In order to avoid the “big mistake” of trying to fit too much in, consolidate your decisions. 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. You would be surprised how many things there are to try in each place you visit if you just take the time to look.

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 Rome Food TourVenice Food Tour, and Florence Food Tour.

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!

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

by Gina Mussio

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

  1. Meenal says:

    I discovered your blog while researching for our tentative trip to Italy this June. We will be traveling with our children 7 & 14 yrs. We have already been to Rome and Venice. I wanted to know how feasible it is to combine Florence, a bit of Tuscany and the Amalfi Coast in one trip. We could fly in and out of Milan , so probably a couple of days there as well.How many days would it take to do it comfortably. We are thinking 2 weeks but we could stretch it a little. Thanks.

    • Walks of Italy says:

      Hi Meenal,

      We think that two weeks is a good estimate, though more is always better 🙂 All of Italy is well connected by train, so transport shouldn’t be too much of a problem if you don’t mind spending time. You can take a fast train from Florence to Naples, then you’ll change onto a regional train from there down to Sorrento or another town along the Amalfi Coast. From Florence to Sorrento it should take you just a bit over 2 hours. Still, we suggest counting travel days as half days when budgeting your time! This way you could spend 3 days in Milan, 3 days in Florence, choose one or two towns in the Tuscan countryside for another 2 or 3 days, then spend the rest of the time down along the Amalfi Coast. Get the most of your time with guided tours. Our Tuscany Day Trip Tour parts from Florence and visits Siena, San Gimignano and Chianti for a Tuscan lunch on a vineyard.

    • Dino says:

      First timer here, very helpful thoughts.
      Why is it I have this pre conceived notion that the theft in the bigger cities is rampant
      I have heard too many stories. what are some safe guards, apparently the train is a bad place or way to travel when busy.

      also did you exchange your money there or do you pre fer to use amex or visa while abroad

  2. Anne Golembeski says:

    I lived in northern Italy for four years and have visited often since. The tourist attractions are great. I went to Pisa and the Vatican Museum and the Cinque Terra. All fantastic because I had the time. If you have limited time just walk! Walk the city streets and the neighborhoods and piazzas. Don’t skip the small unknown towns. That’s where you’ll find the local festas and shops. You’ll see beautiful architecture. The best times in my experience were just walking the small villages.

  3. Tania says:

    Me and my husband (30s) are travelling to Venice on Aug 15 2016. We will be staying there for 2 days. Can you please let me know what all can be visited on Aug 15th (saw St. Marks Basilica and other places is closed.) Will shops and eat-outs be opened? We are not much into history. we want to walk on the streets to find good food and get a flavor of the Venetian culture and of-course some cheap shopping if possible. Can you suggest places where we can hang around?

    • Walks of Italy says:

      Hi Tania,

      Most major attractions will be closed, but there will be a few restaurants open to serve the people celebrating the holiday and for the tourists as well! We suggest taking the day to stroll the city as much as possible and get lost down the hundreds of alleyways and over the beautiful bridges. The waterbus will still be running, though probably with limited frequency, so you could consider visiting the multicolored houses of Burano while you’re there as well, which doesn’t require any museum or church visit! Have a great trip!

    • Agnes Phillips says:

      We were there 4 years ago around this time in August. We did Venice on a day trip from Florence. It was hot! I mean 100F hot! Very little refuge from the heat in Venice if you are walking around. There were restaurants and shops open but what they call air conditioning is not to the standards of us Americans. I loved Venice but this was peak tourist season. Water taxis and ferries were so crowded, I feared we’d tip over. When I go again and I want to go again, I will go in the spring or late fall.

  4. Jade says:

    Your blog is really helping me plan my trip so thank you!
    I am really struggling to narrow down the places I want to visit. I have a two week window and I would like to see Rome, Amalfi Coast, Florence, Venice & Lake Garda, do this sound doable?
    Can you also help with the travel times between the places, how long should I set aside for travelling? Thank You

    • Walks of Italy says:

      Hi Jade,

      We know that it’s hard to narrow down an itinerary when there are so many beautiful places to see! We suggest sticking to places relatively nearby, and giving yourself plenty of time to explore the big cities filled with history and art, such as Rome and Florence. Another trick, is to see the city with the help of expert local guides! Perhaps our tours in Rome, Florence and Venice can help you get the most out the time you dedicate to each. For example, if you decide that there’s not enough time to dedicate to the Amalfi Coast but you’re just dying to see it, try our Pompeii Tour From Rome with Private Amalfi Coast Drive. That way with just one short day trip you can tour Pompeii and relax on your private drive along the coast. Hope to see you there!

  5. Athena says:

    I am planning to visit Italy this year. I was planning for a two weeks trip and after reading this article I change my plans, I should make 1 month trip to see Italy to its full ?!!? Replanning it is ! !

    • Walks of Italy says:

      Hi Athena,

      That just depends on how many places you’re planning on visiting! You can see something in Italy in 3 days just like you can one month, but you’ll have to adjust the quantity of destinations to get the best quality experience.

  6. Siddharth says:

    Hi I will be travelling to Italy in July for 10 nights. I will be flying in and out of Milan. I have 2 tentative plans . Need your help in deciding between the two. 2 days Milan(including lake Como) – 2 days Amalfi and Sorrento-2 days Rome+vatican- 3 days Florence. I am missing Venice here. Now in the second itenary Amalfi and Sorrento will be replaced Venice. Need your suggestions.

    • Walks of Italy says:

      Hi Siddharth,

      Personally, we think that’s a lot of traveling to do in just 10 days, and would suggest trying to stay longer in Rome and/or the Amalfi Coast. Still, we know it can be hard to decide. Tours can help you to make the most out of the time that you do have, however. For example, our day trip from Rome tour will take you on a Pompeii tour guided by an expert and for a private drive along the Amalfi Coast, helping you to see some of the area in the most efficient way possible, in just a day!

  7. Gloria Barr says:

    Really great advice! Will pass that on to all our followers.

  8. On my own says:

    I had planned a trip with a friend, who unfortunately has some medical problems and won’t be able to make the trip. I’ve decided to go alone, so would love some advice on how to spend my time. I’m arriving in Naples and flying out of Barcelona two weeks later. I’ve already been to Rome, Tuscany and Florence. Since I’m going in July, I would love to avoid the major touristy places and perhaps find some quieter places to enjoy good food, beauty and history. Any suggestion would be appreciated. Oh, and is Bellagio worth a visit and the prices?

    • Walks of Italy says:

      We’re sorry to hear about your friend, but happy that you’re coming to Il Bel Paese in any case! Considering that you’re arriving in Naples, we’d suggest staying in that region or going further south. The Amalfi Coast is always worth the visit, though we can’t promise it won’t be a bit touristy already in July. If you really want to escape the tourists, head to the countryside. The countryside of Lazio is lush, beautiful, and filled with art and history. Further south in Calabria or Puglia will offer you a lot of relax with breathtaking views. Bellagio up north is a gorgeous town along Lake Como. We believe it is worth it, but considering that it’s so small you won’t need more than a day to explore the entire town. After, you can take the ferry around to Como and the many other beautiful towns along the lake. That said, it’s a long trip from Naples!

  9. Todd says:

    Hi, my family & I have a 10 day trip to Italy planned in a few days. We are flying into Rome, then Florence, & Venice. We have two daughters who are 22 & 19 yrs. old. Our family usually vacations at beaches. Should we try to plan at least a partial day at some of the beautiful beaches for each city or just 1 beach destination in one of the cities? I don’t think my daughters will be overly interested in the historical aspects of Italy, but we have some planned sightseeing activities to at least see the major attractions. It would be nice to have some relaxing time on a beach, but not sure if we’ll have enough time. Please let me know your thoughts. Your blog is awesome, very helpful with great information.

    • Walks of Italy says:

      Hi Todd,

      Most of Italy’s historical cities aren’t actually that near to a beach. In that case, we suggest carving out a day to head to the beach from Rome, which likely has the nicest beach nearby of the three cities. Have a great trip!

  10. Christy says:

    What a great blog! Thank you so much. We are flying into Venice, and arrive in the moring, spending one night and heading to Florence. We will be in Florence for 2 nights and then Positano for three nights, and finally Rome for 3 nights. We fly out of Rome. What is the best way to get from Florence to Positano. I am thinking of taking the train to Sorrento and then the ferry.

  11. Jessica says:

    Hi! I love your page, so informative!
    Question, I am flying into Milan on a wed afternoon 4:00pm and depart on Monday evening from Rome. Ideally would like to do one night Milan, two nights Florence, two nights Rome with a day trip to positano- Is this too much for such a short time? 🙁 we were also thinking of driving, but will this be much longer?
    Thank you for any help!!!

    • Walks of Italy says:

      Hi Jessica,

      Yes, that itinerary does sound a little bit too packed, especially just considering transport times. It will take longer than to drive as opposed to high speed trains, but the high speed trains connect Milan to Florence and Rome easily. We suggest cutting out Positano for this trip, it’s quite a long way from Rome for just one day when there is so much transport time needed. Let us know what you decide! 🙂

  12. Tom Reed says:

    my wife and I are planning a two week trip to Italy in early October for our 30th. She is Italian and never been to her Homeland. We love wine, great food, beautiful scenery and History…I hear the Amalfi Coast is nice too:)
    Venice, Florence, Rome, Naples and the Amalfi Coast are all points of interest. Considering this is our first visit to Italy and we’ll be there in early October. What do you suggest for an overall plan with rhythm?

    • Walks of Italy says:

      Hi Tom,

      We suggest you scroll through the blog to get ideas for possible itineraries, or use this post to decide if you want a major cities trip, a regional itinerary or a themed one 🙂 Just be sure to not pack in too much!

  13. Jessica Ray says:

    I really looking for this type of information.. Becoz i also planning for trip to italy and this article really gives me some important information which i really required such as time and duration of trip etc..

    Thanks for sharing such a great experience with us,

  14. Ina T Phelps says:

    We are flying in to Naples in Mid Oct and staying for 8days. Considering a short period of time, please advise the best 3 places to stay and what are the surrounding/nearby towns best attractions.