10 Days in Italy: A Complete Itinerary for First Timers

One thing I don’t think people really understand – I certainly didn’t – before they learn more about Italy is how diverse Italy is from a historical, cultural, and political perspective. Italy is one of the youngest countries in the European Union, having only been unified in 1861. 

Of course, it’s hard to picture that given our conceptions about the Roman Empire and their control over the Italian Peninsula, but for the past thousand years or so, it has been a smorgasbord of various city-states and independent republics that were constantly vying for power.

And they all had different political structures, cultural quirks, and, perhaps most importantly, food and drink specialties. 

Over the course of your time in Italy, we hope that you’ll get a taste for what makes each region that you spend time in special, and we’re here to help you figure out how to spend 10 days exploring that regional diversity, seeing the main sights along with some less-visited places (Bologna!) that we love. 

Anyway, our point is that Italy is amazing. We love Italy, and you should go (and be smart about how you structure your trip). 

If you’re planning a trip to Italy with 10 days to spend and you’re not sure where to start, this guide is for you! 

We’re going to give you our version of the best way to spend 10 days in Italy for the first time all based on our own experiences over the course of multiple trips including Alysha’s six month stint living in Rome, almost six weeks in Italy a few years back, and another three weeks in 2022. 

As if that wasn’t enough, Matt just got back from a trip to Rome in the spring of 2024, and we’re planning a trip to the Dolomites in the summer of 2025. 

As you can pretty clearly see, we can’t get enough Italy in our lives. 

In this guide to planning your 10 day Italy itinerary, here’s what we’re going to cover:

  • Exactly how to plan out your 10 day trip to Italy, including what stops to make, what route to take, and all the important logistics you need to know

  • A guide to what to do, where to stay, and how to get there for each stop on the itinerary

  • Options for shorter and longer trips if you have more or less time in Italy

Throughout the guide, we’ll share our favorite finds and experiences in Italy based on our multiple trips (including six weeks in Italy a couple of years ago, a more recent three week trip in the fall of 2022, and a relatively short trip to Rome in 2024) to help you plan your unforgettable trip.

Sound good to you? Let’s get into it.

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and book. That being said, we would never recommend something to you that we don’t stand behind 100%.

How Much Can You See With 10 Days?

The first thing we need to do as we get into exactly how to plan your itinerary is set expectations about what is possible with 10 days. 

Italy is a big, big country, and 10 days is barely enough time to scratch the surface. 10 days is a great start to exploring Italy, but you’re going to have to pick and choose what to focus on.

I mean, I (Matt here!) have spent a full two and a half months in Italy over the past several years (including a five day stay in Rome in the spring of 2024), and I STILL haven’t made it to all the places I want to make it to (though I’ve made a good dent in my list now – Dolomites in the summer of 2025, here we come!). 

We’d urge you to resist the temptation to continuously add places to your itinerary until you’re scooting around Italy like a madman (or madwoman), changing cities every day and sprinting between museums. 

We’ve been there. Trust us. 

We completely understand the temptation, have fallen victim to it many times, and are here to tell you that your trip will be much more relaxing, rewarding, and memorable if you spend more time in fewer places.

10 days is enough time to see some of the main highlights (like Rome and Venice), connect with locals and see their cities and countries through a different lens, eat some great food and drink some excellent wine (duh), and get a taste for what makes Italy special (and to populate your list for places you want to go on your return trip!). 

We’ve also found time to visit some of our favorite underrated, less visited cities in Italy – namely Bologna (our favorite city in Italy) and Verona – along the way. 

How to Structure Your Itinerary

As we’ve traveled more and more over the past several years, we’ve come to realize that we have a strong perspective on how to approach a longer trip (10+ days). 

The first thing we want to say here is that you should dedicate at least 2-3 days to each of Italy’s big cities like Rome, Venice, Florence, or Milan

Trying to do any of those cities in a day is going to be mayhem, and you will inevitably be checked out and ready for a nap in the early afternoon as you’re heading to your next attraction. 

The reason that multiple days are better is to split up the main attractions. 

Take Rome, whose two main attractions are the Colosseum and the Vatican in our minds. Trying to do those two things on the same day is going to sap you of all of your energy, and you won’t be able to focus on whichever one comes second. 

Always always always split up those bigger attractions so that they fall on separate days when you can!

We also believe that it is almost always better to choose a home base for a longer period and do day trips from there rather than moving around every day or two.

In this case, with 10 days, we’d pick a maximum of three cities you want to use as a home base, and divide your time roughly equally between them. 

For your first trip to Italy, we think those three cities should be Rome, Florence, and Venice

Those three cities are great places to visit in their own right from a culture, history, and food perspective, but also are easily connected with Italy’s high speed train network. Plus, Florence in particular makes for a great home base for exploring multiple other places via day trip.

Where to Start and End Your Trip to Italy

The next thing to think about as you’re planning your trip is where you’re going to start and end your trip to Italy. 

The first thing to know is that, if you can, you should book an “open jaw” flight – a flight that arrives in one city and departs from another – to cut down on backtracking and extra travel time. 

If you follow the itinerary below as written, you’ll want to fly into Rome’s Leonardo da Vinci–Fiumicino Airport (FCO) and fly out of Venice’s Marco Polo Airport (VCE). 

Both are big international airports, but will likely require a connection if you’re coming from outside of Europe (usually that connection will be London, Amsterdam, Paris, or Frankfurt, but it depends on the airline). 

The other good international airports in Italy are in Milan, where there are actually two options, Malapensa (MXP) and Linate (LIN). 

How to Get Around Once You’re in Italy

After you’ve arrived in Italy, the next thing to talk through is getting around within Italy. 

The first thing we want to say is that you really, really don’t need to rent a car to do this trip

In fact, we’d advise against it if you’re following the itinerary below as written (or close to it) because the car is going to be more of a hindrance than help in the cities, which is where you’ll spend most of your time (doing day trips from your home base in each city).

The second thing to know is that Italy has a robust train network, and that’s what you should use to get between cities. 

You could fly between cities on this itinerary, but we highly recommend taking the train for a more pleasant and often more efficient journey.

We LOVE train travel (especially high speed train travel), and it is by far the most efficient way to connect the big cities. 

A few things to know about train travel in Italy: 

First, there are (essentially) two types of trains in Italy – high speed and regional – and they operate differently.

  • High speed trains are more expensive, significantly faster, and less flexible. To save time since you’ve only got a limited amount of it in Italy, you’ll want to take the high speed trains between cities. You’ll want to book your ticket as far in advance as possible, which usually will save you some money, but will be less flexible. If you want the flexibility, you’ll have to be prepared to pay a little extra.

  • Regional trains are slower, cheaper, and more flexible. They’re usually for connecting nearby smaller cities to each other (for example, there’s a regional train between Florence and Pisa). You can buy these tickets when you arrive at the station, and they’re more flexible. You need to make sure you validate them before boarding.

We’d take high speed trains between Rome and Florence, and between Florence and Venice. 

For some of the day trips from Florence, regional trains will do.

The website for booking trains directly is Trenitalia, and it’s actually fairly streamlined and user-friendly. They even have a (mostly) functional app!

The only hiccup is that you need to know the name of the train station in Italian (e.g. typing “Venice” doesn’t work – you have to type “Veneto,” which is just Venice in Italian). 

If you’re not comfortable with that, we’ve used Omio often to book trains around Europe, which is generally a far more streamlined experience (in English, no less).

How to Plan an Incredible 10 Day Italy Itinerary

Here’s what the itinerary you’re going to find below looks like written out. 

  • Day 0: Arrive in Rome
  • Day 1: Rome
  • Day 2: Rome
  • Day 3: Rome
  • Day 4: Train to Florence + Explore Florence
  • Day 5: Florence
  • Day 6: Day Trip to Bologna
  • Day 7: Day Trip to Siena
  • Day 8: Train to Venice (early morning)
  • Day 9: Venice
  • Day 10: Venice + Fly Home

Obviously, you’ll have to massage this itinerary a little bit to make it work with your specific flights.

We’re assuming you have 10 full days in Italy, not including the half days that would be dedicated to your arriving and departing flights. 

Note that this is very much a classic Italy itinerary that is meant to help you figure out the best way to see the main highlights in Italy with ten days (according to, well, us, who have spent a lot of time in Italy over the past several years – more than two months in total!). 

Obviously, there is a LOT to see in Italy, and we have plenty of ideas on how to make changes to this itinerary. 

For example, you could do a southern Italy itinerary that focuses more on Naples and the Amalfi Coast after spending a few days in Rome, or a northern Italy itinerary that focuses on the Dolomites, Lake Como, and Milan. It all depends on what you’re looking for. 

You’ll find some of our ideas in the “with more time” section below, which you can use to make changes to your itinerary based on your specific style and needs. 

Days 1-3: Rome

Ah, Roma. Collectively we’ve spent quite a bit of time in Rome now. I (Matt here) have been to Rome five or six times (it’s hard to keep track at this point!), including a recent trip in the spring of 2024.

Alysha has been a similar number of times, including a six month stint living in Rome. 

We love Rome, and I love talking to people about Rome because many people use adjectives like “dirty” and “chaotic” to describe it, and they mean it in a negative way. 

And, to be honest, those adjectives are almost 100% deserved. But, for us, that’s part of the charm of Rome. We’re city people, and the sheer energy that you feel walking around Rome is similar to the energy you feel wandering around New York City, though significantly less overwhelming. 

There is a ton of history in Rome, and it’s a great place to learn about not only the Roman empire, which was centered in Rome, but also the modern state of Italy, which is one of the newest countries in Europe having only been unified in the 19th Century after centuries of being a collection of independent states with different laws, languages, and cultures.  

We also really like the food culture in Rome. Contrary to what you’d expect if you’re picturing the opulence of Ancient Rome, the ingredients used in modern Roman cuisine are much more modest.

The four Roman pastas – Carbonara, Amatriciana, Cacio e Pepe, and Alla Gricia – are all very rustic, as are the fried artichokes, supplì (fried rice balls similar to arancini), and pizza al taglio that make up the other main staples in Rome.

Getting From the Airport to Rome

In all likelihood, you’ll be flying into Rome’s Fiumicino Airport (FCO), which is the busiest airport in Italy. 

The easiest way to get from the airport to the city center is going to be taking the Leonardo Express, a direct, air conditioned train that runs directly from the airport to Termini Station, Rome’s main train station. 

The advantages here far outweigh the disadvantages. You’re not subject to the near-constant traffic in Rome, it’s clean, comfortable, and affordable, and it’s easy to find in the airport. 

The only downside is that, depending on where you’re staying, you might need to take a taxi or bus from Termini Station to your hotel. 

If you’re coming from within Europe (especially on a budget airline), there’s a chance you’ll come into Ciampino Airport (CIA), which is far more limited in terms of ways to get to the city center, but takes about the same amount of time in the end if you take the Ciampino Airlink

What to Do in Rome

Here are some things that we think you definitely shouldn’t miss while you’re in Rome. 

Our most important tip here is to not do multiple big attractions (e.g. the Colosseum, Vatican, or Borghese Gallery) on the same day, because you will be exhausted by the time you START the second attraction. 

That’s also part of the reason why we recommend 2+ days in each city – so you have time to split things up and do the main attractions on separate days. 

The Colosseum & Roman Forum: The Colosseum and Roman Forum are the first of the two big tourist attractions in Rome, and it’s something you’re not going to want to miss. First of all, we’d highly recommend heading to this garden early in the morning or late at night for an excellent view (and picture) of the Colosseum, and this viewpoint for a great view of the Forum from above. Second of all, if you only have time or budget for one guided tour in Rome, it should probably be here. It’s hard to wrap your head around what you’re seeing as you walk through the mostly crumbling buildings, and a guide will help you contextualize and comprehend the history you’re seeing, which will lead to a much richer experience in the end (which is what we’re always looking for!). We have personally done both this guided tour, which is a great dive into this rich piece of history, and also this nighttime VIP tour, which takes you under the floor of the Colosseum at night, when it is MUCH quieter than the daytime tours (but, crucially, DOES NOT visit the Forum). Both are with Walks of Italy, our favorite tour company in Italy – you can read more about our experience on the Colosseum tour that challenged our preconceived notions.   

The Colosseum at night is a very different experience – cool and calm!

Marvel at the Collection at the Vatican Museums (and St. Peter’s Basilica): I have now visited the Vatican Museums and St. Peter’s Basilica three separate times across multiple trips, and I can confidently say that I still don’t think I’ve seen everything. The Vatican Museums is a truly mindblowing collection of art that the Catholic Church has either accumulated or commissioned over the course of its centuries as one of the main power centers in Europe. There are two aspects here – the Museums (which includes the Sistine Chapel) and St. Peter’s Basilica, and you’ll want to see both. It’s going to take the vast majority of the day to do both, because it’s A LOT. The other thing we’d say is that you’ll want to get in as early as humanly possible, because it’s EXTREMELY busy and claustrophobic at peak times. Book your entry tickets well in advance, and select the earliest time slot of the day. On my last trip, I did this early morning tour with Walks of Italy, which was great (however, it is worth noting that there will be other people in the Sistine Chapel due to changes that the Vatican has made to visitor hours over the past few years – if you truly want to be alone, you’ll have to splurge on this tour where you’re there when they open the doors to the Sistine Chapel). 

Walking the Centro Storico (in the early morning!): The Centro Storico is Rome’s historic center (though most of the ornate fountains and buildings you see today are actually from the Baroque period in the 17th Century, ish). It’s a treasure trove of the most famous sites in Rome, including Piazza Navona, Campo de’ Fiori, the Pantheon, and, of course, the Trevi Fountain. Once again, this is something you should do as early in the morning as you possibly can because otherwise, the cobbled, narrow streets in this part of the city are packed wall-to-wall with visitors all wanting to see the same things you do. Get out here between 7am and 8am and it’s a much different story. Here’s a route that we have done multiple times, and gets you to the main sites (start from the northern end, and don’t skip Terrazza del Pincio for excellent views of the city). Along the way, stop at either Tazza d’Oro or Sant’ Eustachio for a quintessential Italian coffee experience (stand at the bar, order a cafe or cappuccino, and enjoy the ruthless efficiency of the baristas). 

Spend an Evening in Trastevere: Trastevere is our favorite part of Rome. It’s all narrow cobblestone streets, charming piazzas, a lively atmosphere, and great places to eat and drink. We think it’s at its best in the evening, when it’s packed with people wandering the streets, eating on one of the many al fresco patios, and hanging out in its many piazzas. A few favorites: Fatamorgana for gelato, Les Vignerons for a nice selection of beer and wine by the bottle, Supplì Roma for a Roman classic (similar to arancini in Sicily), and Enoteca Cuverie for a nice, quiet wine bar in a quieter part of the neighborhood. 

Seek Out the Best Views in Rome: One of our favorite parts about Rome is the view from above, because it’s a sea of domes as far as the eye can see (almost literally). We have a couple of favorite viewpoints, including the previously mentioned Terrazza del Pincio (here on Google Maps). We also really like the view from the Giardino degli Aranci (“Orange Garden” – here on Google Maps) and from the top of Castel Sant’Angelo (which is definitely worth a visit – here on Google Maps). One last viewpoint is the walk up to Piazza Garibaldi, which is a piazza above Trastevere with excellent views of the city (here’s a route that takes you to a couple of other nice sites along the way). 

People enjoying the views at the Giardino degli Aranci in the late afternoon
The view from Terrazza del Pincio

Obviously, Rome is a huge, complex, history-filled city, and there is plenty more to do, see, eat, and drink in it.

For more, we’d point you to our 4 day Rome itinerary and our guide to the best things to do in Rome (for first timers), which have all of our favorite things to do, see, eat, and drink in the Italian capital. 

Where to Stay in Rome

We’ve spent multiple weeks in Rome over the past few years, and Alysha lived there for six months in college, so we think that we have a better than average working knowledge of Rome’s neighborhoods, at least compared to people who have only spent a few days there.

In our minds, there are really only two options when it comes to neighborhoods we like to stay in. 

For all of the details behind this summary below, we’d point you to our more detailed guide to the best places to stay in Rome, which has a complete neighborhood guide for all of the neighborhoods mentioned below. 

The first (and best for first timers, we think) is the Centro Storico, which is the charming historic center of Rome – specifically the southwestern end between Campo de’ Fiori and Piazza Navona. 

Many of our favorites in Rome – our favorite walk, our favorite Italian-style coffee bar, our favorite wine bar – are tucked away in this network of cobblestone streets, and it’s about as central as you can get. 

The downside is that it is absolutely packed with tourists between 10am and 7pm, and it’s going to be a little more expensive (you’re paying for the location). 

We spent a week here recently, and we wanted an apartment with a little more room to spread out (plus, a kitchen) and stayed at these lovely apartments, which we’d wholeheartedly recommend.

It’s in a great location too – just 10 minutes on foot to the center of all the action. 

The second area to consider, and our absolute favorite neighborhood in Rome, is Trastevere.

We stayed there for the last leg of our long trip to Rome a few years ago (after Matt had stayed there before) and fell in love all over again. 

Charming cobblestone streets, narrow alleyways with ivy-lined buildings, cafes spilling out into piazzas at the foot of churches. It’s the most romantic part of Rome. It also has some of the best nightlife in Rome. 

We stayed at Horti 14 Borgo on our last trip together (Matt has since been solo in the spring of 2024), which was a bit of a splurge for us, but the friendly service, incredible breakfast spread (which is included), and quiet location made it worth it. 

Days 4-7: Florence + Day Trips to Bologna & Siena

Florence and Rome as the first two stops on this itinerary provide you a nice contrast, because we think they’re very different cities despite being only an hour and a half apart by high speed train. 

Rome is massive, sprawling, and chaotic. Florence is compact and busy, but doesn’t have the same “am I going to get run over by a scooter crossing the street” vibe that Rome does. It’s a much more organized, controlled chaos, if that makes sense. 

The main difference in our view is the fact that, starting in the 15th and 16th Centuries, Florence was one of the wealthiest cities in the world, and was on the forefront of the Renaissance (if not the movement’s birthplace). Contrast that with Rome, which has not been a terribly wealthy city in the past 1,000 years (if not more). 

The difference between Rome and Florence is kind of like the difference between the Colosseum and Roman Forum and the Vatican Museums and St. Peter’s Basilica.

The first is a big important historical site, but it’s relatively modest in its decoration (as modest as a massive arena built a couple thousand years ago can be), the second is much more ornate and projects the obscene wealth that went into the commissioning of the various pieces of it.

The thing to keep in mind here is the fact that the relationship between wealth and art flows in that direction. Wealth brings the ability to commission the most famous artists in the world to create all the beautiful art you see in Florence today. 

The result of all the wealth that flowed into Florence is a more modern city than Rome is, with incredible architecture that features more ornate decorations than Rome. 

Plus, the collection of art in the city’s museums – the Uffizi Gallery and the Galleria dell’Accademia di Firenze (home of Michaelangelo’s famous statue of David) – is second to none, and it’s a great place to learn about how the Renaissance fundamentally changed art forever.  

As we mentioned above, Florence is no less busy than Rome, but the compact nature of the city center means the same number of people are packed into a much smaller space. Walking through all corners of Florence’s city center feels sort of similar to Rome’s Centro Storico in terms of being packed wall-to-wall during peak hours.

However, there are charming corners to be found around Florence (like across the river in Oltrarno), especially in the early morning and later in the evening when the tour buses and day trippers have gone home. 

Getting from Rome to Florence

From Rome, it’s a quick and easy high speed train ride to Florence.

You’ll leave from Rome’s Termini Station, and you want to arrive at Santa Maria Novella in Florence. There are many, many trains running this route each day.  

To maximize your time, you’re going to want to book either the “Frecciarossa” or “Italo” trains, which cover the distance in an hour and a half (versus three hours or so on a regional train line). 

For your purposes, Frecciarossa (run by Trenitalia, the national rail company) and Italo (run by a private company) are essentially the same. Pick whichever one is best in terms of timing and prices. 

What to Do in Florence

Here are some things that we think you definitely shouldn’t miss while you’re in Florence. 

The Uffizi Gallery: If you only have time for one tour in Florence, this is by far our top pick for the destination. The Uffizi Gallery is a collection of art that focuses on the Renaissance, and it’s organized in (roughly) chronological order so that you can see the progression as the movement took hold of the artists working in Florence. I’ve done it three times – once on my own, and two separate tours – and I’d highly recommend a tour here, if you can swing it. A tour is going to help you understand the pieces themselves – there are countless details in each piece of art that we never would notice without someone explaining them to us – and how they fit into the broader story of the Renaissance and its impact on art history. Of the tours I’ve done, this tour was by far the best crash course, and it ends inside the museum so you can spend more time, if you’d like. 

The Statue of David: I’ve read a lot of travel guides about the famous statue of David, which is housed inside the Galleria dell’Accademia di Firenze today, that say something to the effect of “just go see the replica of the statue in piazza della Signoria, which is free.” And, if you have limited time, I would definitely focus on the Uffizi Gallery. However, I do think that there is a lot of interesting work from Michelangelo in the Accademia that tells a story of how he worked his way to making the David. If you’re interested in that progression and the artist’s fascination with the human body, it’s worth spending an hour or two in the Accademia (and seeing the statue in that context here you can walk all the way around it is also cool). Book your tickets well in advance – we’re talking as soon as you know you’ll be in Florence – to avoid standing in the ticket office line (you will still have to stand in the security line), which you can do on the official website. I’ve also done this guided tour of the gallery with my mom, which allows you to skip the long lines (and get tickets if they’re sold out through the official site) and it was a great overview of the story of Michelangelo and his career leading up to the David. 

The Duomo: The Duomo di Firenze (also known as the Cattedrale di Santa Maria del Fiore) is massive, and is the centerpiece of Florence’s historic center. It was constructed over the course of 150 years or so, starting at the end of the 13th Century and being consecrated in 1436 (though the facade wasn’t actually completely finished until the 19th Century). There are multiple components to see here, and of them all, the one we’d focus on is Brunelleschi’s dome, which is impressive both on the inside and the outside, where you’ll find sweeping views out over the city of Florence. The climb to the top of the dome does require a steep, narrow staircase with 400+ steps, which isn’t for everyone. However, you get excellent views of the interior of the dome as you pass along a walkway just below the dome (which can get claustrophobic as people stop to marvel at the art). You can buy tickets here, and if you want to climb the dome, you’ll need to get the “Brunelleschi Pass” – the only ticket that includes climbing the dome. Choose either the earliest or latest time slot for the smallest crowds. 

The view from the top of the Duomo di Firenze

Piazzale Michelangelo & Oltrarno: Aside from the view from the dome, this is probably our favorite view of Florence. It’s on the other side of the Arno River (the river that runs through Florence), and it’s worth spending an afternoon exploring this less-visited neighborhood (though, it’s still Florence, so expect to see plenty of tourists). Our recommendation would be to walk up to the piazza and back down through Oltrarno, stopping for wine at Le Volpi e l’Uva (which has wine from all over Italy, including some local varietals), gelato at Gelateria Della Passera (recommended by Alysha AND our host at a local winery), and Ditta Artiginale for coffee (Matt’s favorite coffee on this side of the river) on your way down to Piazza Santo Spirito, the beating heart of the neighborhood. Here’s a map of the route with our favorite stops on Google Maps. 

Alysha at Piazzale Michelangelo on our latest trip to Florence
The view of Ponte Vecchio from Piazzale Michelangelo

Take a Day Trip to Bologna: Bologna is the capital of Emilia-Romagna, the region immediately north of Tuscany, and it’s our favorite city in Italy. First of all, the food is unparalleled. Bolognese, prosciutto di Parma, balsamic vinegar of Modena, parmesan-reggiano, mortadella – it all comes from the area around Bologna! Plus, it is a gorgeous college town with a youthful energy and a TINY fraction of the tourists you’ll see in most other cities in Italy. We love Bologna, and it’s the first place we’d add more time if you have it (for more, see the “with more time section” below the itinerary). We have an entire guide dedicated to spending one amazing day in Bologna, which has all the details you need to plan your day trip (including how to get there, what to do and see, and what to eat and drink). 

Take a Day Trip to Siena: Tuscany – the broader region that Florence is the capital of – is known for its hilltop towns, which dot the landscape in the heart of Tuscany to the south of Florence. Siena is, perhaps, the best example of this phenomenon. More importantly, it’s the most accessible by public transportation, and it’s an easy train (or bus) ride away from Florence. When you’re in Siena, we definitely wouldn’t miss the Duomo di Siena (and its incredible tiled floor, if it’s uncovered for the season!), the climb up to the Facciatone (observation deck with great views of the cathedral), and this walking tour that we enjoyed, which gives you a great overview of the city and its history as a powerful city-state in central Italy. 

Obviously, Florence is a complex, history-filled city, and there is plenty more to do, see, eat, and drink than the few bullets above. 

For more, we’d point you to our 3 day Florence itinerary and our guide to the best things to do in Florence (for first timers), which have all of our favorite things to do, see, eat, and drink. 

Where to Stay in Florence

Florence’s city center is pretty compact as big Italian cities go, which means it matters slightly less where you stay because it’s all within a 15 minute walk of the main sights. 

However, there are two areas that stick out in our minds as our favorite neighborhoods in Florence. 

We stayed in Santa Croce (also called Sant’Ambrogio) – the neighborhood where Leonardo Davinci grew up that is named after the church, where he is buried – and it’s a great option because it’s central, but far enough removed from the historic center to have fewer tourists (slightly) and better places to eat and drink.

From there, you’ll be able to walk to the Duomo, Piazza della Signoria, and the river, all within 15 minutes or so. 

We stayed at Pietrapiana Boutique Apartments, which were tucked away in a quiet courtyard away from the hustle and bustle with beautiful, spacious rooms. It was one of our favorite stays in Italy. 

If you’re looking for a more traditional hotel (that’s also fairly affordable), look at the Eurostars Hotel a few blocks southeast of the church.   

The other place we’d like to stay (though we haven’t stayed there yet) is Oltrarno, which is in many ways a more authentic version of Florence, where locals actually live.

It’s just across the Arno River from the Centro Storico, which is where you’ll find a few of the best views in Florence (including the famous Piazzale Michelangelo). 

The result is a vibrant neighborhood with a good selection of food and drinks, charming piazzas, all within a 15 minute walk of the main attractions in Florence. 

The downside of staying here is that there are far fewer options in terms of hotels and guesthouses. 

For all of the details behind this summary below, we’d point you to our more detailed guide to the best places to stay in Florence, which has a complete neighborhood guide for the neighborhoods mentioned above. 

Days 8-10: Venice + Day Trip to Verona

We have somewhat mixed feelings about Venice, and contemplated completely skipping Venice in favor of Milan here in this itinerary. 

Venice is a city that has been plagued by overtourism for decades, and the reason why it matters is the simple fact that a city like Venice – which famously sits on a series of canals – is just not built to handle the sheer number of people that descend on it on a daily basis, year round. 

This is especially true when the cruise ships dock and flood the relatively small city center of Venice with thousands of tourists, which is a growing challenge facing the city because the infrastructure is just not built to handle it.  

However, after multiple conversations about it, we do think Venice is worth seeing once, especially if you’re able to spend a few days there to see it at its best – which is to say in the early mornings and evenings, when the city empties out and is a much more tranquil experience. 

If you’re going to include Venice, we’d make sure to include 2-3 days in the city to give yourself plenty of time to see the city, and, with three days, do a day trip to nearby Verona (one of our favorite cities in northern Italy). 

To be fair to Venice, the history here is equally fascinating to the other cities you’ve visited.

As we’ve covered already, Italy was a series of independent city states and republics until the 19th Century, and Venice was among the most prolific and powerful for the last 1,000 years or so (until it all fell apart at the end of the 18th Century). 

You’ll see that wealth, which came primarily from its prowess as a seafaring and merchant power, reflected in the architecture, like the famous bridges and the intricate beauty of St. Mark’s Basilica.

Venice is truly a beautiful city, between the Grand Canal snaking its way through the center and the gorgeous architecture, but it does require some finesse to see it without feeling overwhelmed by the crowds.  

Getting From Florence to Venice

The train ride from Florence to Venice will take a hair over two hours on a high speed train. You want to leave from Santa Maria Novella (again, the most convenient train station in Florence) and arrive at Santa Lucia in Venice

And, again, you’re going to want the high speed train options here – either Frecciarossa or Italo – because it will take half as long (two hours and fifteen minutes) as the regional trains. 

What to Do in Venice

Here are some things that we think you definitely shouldn’t miss while you’re in Venice. 

Piazza San Marco and St. Mark’s Basilica: This basilica offers a different style than anything you’ve seen so far in Italy (assuming you’ve followed this itinerary) with its mosaics, facade, and stunning ornate interior. Construction here began in the 11th Century, and by the 14th Century, Venice’s wealth had grown to a point where they decided to start replacing the less impressive pieces of the facade with things like expensive marble. Then, during the 4th Crusade, they stole a bunch of stuff from Constantinople and brought it back to put in and around the church. The church itself is free to enter, but you can skip the sometimes long lines by reserving a ticket and timeslot in advance for €6 (which you can do here). Given limited time, we’d highly suggest going that route (the lines can be LONG and this completely bypasses that line). If you have the time and budget, it’s worth considering climbing the bell tower for €12, which gives you some nice views out over Venice and the lagoon. Best to book far in advance, because they do sell out and if you don’t get a ticket in advance, you’ll have to wait in the long line. 

The Doge’s Palace: The Doge of Venice was analogous to a Duke, meaning it was the person at the top of the food chain. The Palazzo Ducale (Doge’s Palace) is, as you might have guessed, where the Doge lived and worked. Today, it’s a public museum, and there has been significant resources put towards the restoration and renovation of the interior and exterior (pieces of the palace have burned down multiple times since its construction). The architecture – which is in a style that is unique to Venice, Venetian Gothic – is worth the price of admission. It’s a weird mix of a bunch of different styles we’ve seen around Europe, and it’s very unique (and, of course, ornate). Buy tickets in advance and reserve a timeslot on the official website (you can either buy a combo ticket that includes a bunch of the other public museums in Venice, or a ticket for just the Palazzo Ducale – which you choose depends on what else you want to see in Venice). Heads up: it’s marginally cheaper if you buy a ticket 30+ days in advance of your visit. We haven’t done it ourselves yet, but we’d do the Secret Itineraries guided tour of the palace, which will give you some of the history and context around the importance of the building and the Doge’s role in Venice. 

Ride Around on the Vaporetti: The public ferries in Venice – the Vaporetti (vaporetto is the singular version) – are both a very useful form of public transportation (we’re big fans of ferries as public transit, like the ferries in New York City!) and a tourist attraction in their own right because the best way to see Venice is from the water (we think). This is an opportunity to do just that without the absurdly high prices of the gondola rides (which we’d skip). You can basically do an entire tour of the Grand Canal – the main canal in Venice – on the #2 route for €7 or so, which is kind of cool. 

Head out to Burano and Murano: Venice is known for their handblown glass, and the best way to see it is by heading out to the islands to the north of Venice, Murano and Burano. You can get their on your own by taking the normal vaporetti from this dock (they run roughly every 30 minutes during the day, and the ride takes 30 minutes or so to Murano, double that to Burano). You have to go through Murano to get out to Burano, so you can pretty easily combine them into a nice half day trip. Once you’re out there, there’s a lot of places to see traditional (ish) glass blowing, buy souvenirs, and wander a bit. Our top tip would be to make sure to take some time to get far away from the boat dock, because that will be the most crowded part of the island.  

See the Bridges: As a city full of canals, Venice has some pretty incredible bridges that are both functional and beautiful. The most famous is Rialto Bridge (here on Google Maps), and it’s worth coming here around 7am to see it without the zoo of people that you’ll find here between 9am and 10pm or so. Other bridges to seek out are Ponte dell’Accademia (here on Google Maps) and the Ponte dei Sospiri (Bridge of Sighs, here on Google Maps). There’s a good view of the Bridge of Sighs from this bridge a short walk south. 

A Day Trip to Verona: Verona is another city that we really love, and though it’s not exactly off the beaten path – plenty of tourists come to Verona – it’s certainly on a different level from places like Rome and Venice. Getting to Verona from Venice is an easy 90 minute ride on the regional train line that leaves from Venice’s main train station (you’re going to Verona Porta Nuova). Once you’re in Verona, we’d make sure not to miss the Arena di Verona (check their calendar to see if they have any outdoor concerts while you’re there!) and the Museo Archeologico al Teatro Romano (and it’s lovely theater and views out over Verona). For the best views of Verona, head up to the viewpoint up at Castel San Pietro (here on Google Maps – the walk up through the narrow alleyways is also nice). We have an entire guide to Verona that you should read for more, but our number one tip is DO NOT go to the Casa di Giulietta, which is the most overrated tourist attraction we’ve ever personally experienced.  

The Arena di Verona
The view from Castel San Pietro in Verona

Where to Stay in Venice

The first decision you’ll need to make here is deciding whether or not to stay in Venice itself – meaning in the historic center of Venice along the canals – or in the more modern city on the shore, which is cheaper but requires a train journey to reach the part of Venice you want to visit. 

Because we think Venice is at its best when it has emptied out and all the day trippers have left, we think it really makes sense to pay the premium to stay along the canals here

The next decision you’ll need to make when deciding where to stay is going to be what neighborhood to base yourself in. Despite being on the water, it’s actually not as compact as you might expect (which makes the city all that much more impressive, we think).

Generally speaking, we like the southern end of the city, and think that the adjacent neighborhoods of San Polo (more central, equidistant between the train station and Piazza San Marco) and San Marco (which is the in the southern part of the city, near Piazza San Marco – which means it’s not going to be quiet or low key – but far from the train station). 

What to Do with More Time in Italy

If you have more time in Italy, here are the things we’d add (along with how much time you need to add them). 

We also have an in-depth guide to planning a 14 day Italy itinerary, if you happen to have two weeks to spend. There are even more ideas on what to do with more time there. 

More Time in Bologna (+1-2 Days)

If we’re being completely honest, we would completely skip Venice and spend that extra time in Bologna (or Milan, or Verona), but that’s partially because we’ve seen Venice already, and don’t feel a great need to see it again. 

Bologna is, hands down, our favorite city in Italy. 

Matt plays a lot of soccer at home in Portland and occasionally wears his Bologna FC jersey, and roughly every other time someone recognizes it and says something to the effect of “is that a… Bologna jersey?” 

That conversation usually evolves into some version of Matt telling the person that Bologna is his favorite city in Italy and, on occasion, meeting someone who has lived in Bologna and 100% agrees with that statement (almost always because of the food). 

Bologna is the best food city in Italy, mostly because the region it is the capital of – Emilia Romagna – is the birthplace of many of the Italian ingredients that you know and love.

Prosciutto di Parma, Parmesan-Reggiano, Balsamic Vinegar di Modena, lambrusco (a lovely sparkling red wine, traditionally a dry wine) all come from Emilia Romagna, which is the region immediately to the north of Tuscany. 

You could – and Matt has – spend the better part of a week eating and drinking your way through this part of central Italy, and it actually makes a great home base for exploring other parts of the country because almost every high speed train makes a stop in Bologna, which is at the crossroads of two main high speed rail lines running north-south through Italy. 

We love Bologna, and it’s certainly worth more than a day trip. If you have an extra day or two to spend in Bologna, eating and drinking your way through the youthful, vibrant city, you won’t regret it. 

To plan your extra time, use our guides to spending 2 days in Bologna, and our guide to where to stay in Bologna.

Milan (+1-3 Days)

Of the destinations we could have added to the main itinerary in place of Venice, Milan is a strong second contender for a couple of reasons. 

First, it’s yet another contrast from Rome (and Florence) in that Milan feels significantly more modern and cosmopolitan than those cities. 

There are multiple reasons for this, including but not limited to the wealth in northern Italy (Milan is the financial capital of Italy AND the home of all the Italian fashion brands), the fact that it was seen as sort of a backwater back in Roman times, and the fact that it doesn’t follow stereotypical Italian stereotypes (they swap out pasta for rice, which grows in a prolific fashion in the swampy areas outside of Milan).  

Second, the Duomo di Milano is worth visiting Milan for. It was constructed over hundreds and hundreds of years, which is why it’s sort of a mishmash of architectural styles (it started in the 14th Century and only finished in the mid-20th Century). 

Fun fact: Napoleon crowned himself king of Italy here (there’s a tapestry inside depicting the scene), and there’s a plaque that commemorates that that I saw, said “wait, Napoleon did what now?”, and found myself in a rabbit hole of the history of Napoleon for the next 12-18 months. 

Third, Milan’s airport (really, airports, because there are two main airports just outside of Milan) is the second best international airport in the country in terms of connections, so it’ll likely be an easier flight home. 

Anyway, the point is that Milan is a pretty fascinating city with a good food and drink scene – that features far more global cuisines than you’ll find in Rome, Florence, or Venice – and offers a slightly different look at the diverse history and cultures that you’ll find in Italy. 

We think 1-2 days is enough, and you can add another day to do a day trip to somewhere like Lake Como or Torino. 

Guess what? We have a bunch of guides to help you plan a short trip to Milan!

We have a guide to spending a day in Milan, which fits the main highlights (including the Last Supper) into one action-packed day. 

We also have an extended guide to 2 days in Milan, which is a similar itinerary at a more relaxed pace. 

Last but not least, we have a guide to choosing the best place to stay in Milan based on your particular style and budget, which will be helpful in deciding where to base yourself for your trip. 

Tuscany (+2-7 Days)

Florence, which you already have a nice chunk of time in, is the capital of Tuscany, and it’s worth tacking on anywhere from 3-7 extra days to explore the rest of the region.

A few years ago, Matt spent a week in Tuscany with his mom for her 60th birthday, and we both fell in love with the region (despite the fact that the wine in Tuscany is not our type, for the most part). However, the food and the vibe – that dolce vita – is definitely our thing. 

Tuscany is a relatively large swath of land that, unbeknownst to me until I was standing in Volterra looking at the coast, spans all the way past Pisa to Italy’s western coast. 

However, the part of Tuscany that you probably picture in your mind is the Val d’Orcia, which is just southeast of the city of Siena (also worth a visit) and is where you’ll find the towns of Montepulciano, Montalcino, and Pienza (our personal favorite of the three). 

If you’re interested in rolling hills (that are sometimes green, sometimes golden depending on the time of year), cypress trees, excellent red wine, and rustic, rich food, this is the place for you. 

On the eastern end of Tuscany, you’ll find the tower-filled town of San Gimignano and the hilltop town of Volterra (made famous by the Twilight saga) with its Etruscan roots and Roman ruins. 

Lucky for you, we have an entire guide dedicated to planning a Tuscany itinerary that you can use to figure out what to see with the number of days you have. 

Here’s an overview: 

  • With 1-2 days, do Siena. 
  • With 3-5 days, add the Val d’Orcia (and rent a car).
  • With 6-7 days, add San Gimignano and Volterra 

Sicily (+7-14 Days)

Alysha’s dad’s side of the family immigrated to the United States from Sicily two generations back (so Alysha’s grandfather was born in Sicily), and Matt’s grandfather’s parents were also born in Sicily (here’s hoping we’re not distant relatives). 

We decided to spend a really nice chunk of time in Sicily a few years ago, and found ourselves marveling at two things. 

First, the sheer size of Sicily. Even with three weeks, we spent hours of our Sicily trip driving through towns and past beaches that, I’m certain, were beautiful and worth seeing. 

Second, the sheer amount of history in Sicily. There are innumerable ruins in Sicily, ranging from Greek to Phoenician to Roman to Norman. Combine that history with the beautiful landscapes and the towering mass of Mount Etna and you’ve got yourself a beautiful place to spend a week or two (or more, if you have it). 

Here’s our biggest tip for Sicily: we would strongly suggest limiting yourself to one part of the island if you have anything less than a week. 

If you only have a week, we’d spend it on the southeastern coast around Catania, Siracusa and Ortigia, and Taormina, with day trips inland to Noto and Mount Etna. 

Lucky for you, we have an entire guide dedicated to planning a week in Sicily, focused on that southeastern corner. We’d read that for more detail on how to plan a shorter trip.  

With two weeks or more, expand your trip to the rest of the island. Our favorite spots in Sicily were the Val di Noto, Agrigento, and Palermo, and we have a longer guide to planning your Sicily itinerary for a trip of 10-21 days. 

Cinque Terre (+2-4 Days)

Similar to Venice (and the Amalfi Coast), we have mixed feelings about the Cinque Terre (which means “five towns” in Italian because the area is a chain of five coastal towns just north of Spezia).

On one hand, it’s pretty obvious why people are drawn to this tiny slice of coastal paradise (and why it is a Unesco World Heritage Site). It’s beautiful and dramatic, with steep cliffs and narrow coastal walkways bringing you to towns set into the cliff sides with colorful houses and wonderful sea views. 

On the other hand, it’s also pretty obvious that the infrastructure here is really not meant to have thousands of people per day flooding each of the five towns that make up the Cinque Terre. 

This is another place that we’d only recommend if you have two or more days. Partially because it’s a pain to get to from anywhere in Italy (which means a day trip is probably off the table), partially because it’s a place that, like Venice, you need to have the early mornings and late evenings to truly appreciate, when all the day trippers have exited the towns and they’re (relatively) quiet and peaceful. 

On that 60th birthday trip with my mom a few years back, we picked up my brother and spent four days in Cinque Terre, and I think that’s probably the right amount of time to spend here. There are some great hikes, some great sunset viewpoints, and some good food and wine to be had.

Rather than cover it all here, we have separate guides to planning a Cinque Terre itinerary (including all the logistics), a guide to our favorite things to do in Cinque Terre (for first timers), and a guide to the best places to stay in Cinque Terre.  

We’d head over to those guides to plan a side trip to the Cinque Terre to add onto the main itinerary (and we’d do it between Florence and northern Italy – Milan is the easiest major city to reach Cinque Terre from). 

What to Do with Less Time in Italy

If you find yourself with less than 10 days, we’d strongly recommend reducing the amount of ground you plan on covering in Italy. 

With 8-9 days, we’d go ahead and cut some of the day trips from either Florence or Venice and focus instead on seeing the cities themselves. 

With 7 days, you have two options, and it depends on what you’re looking for out of your trip to Italy. 

Your first option is to follow our 7 day Italy itinerary, which is basically a more fast-paced, condensed version of this itinerary that has you visiting Rome, Florence, and Venice over the course of a week. 

Your second option would be to split your time between two cities, use them as a base for day trips, and move a little slower. You could do something like Rome and Florence (or Bologna) and cover a lot of ground in central Italy. 

With five or six days, we’d opt to split time between Rome and Florence, basically following the first chunk of this itinerary as written with three (ish) days in Rome and Florence.  

Anything less than five days? Spend your time in one city (we’d do either Rome, or Bologna as a wildcard) and use it as a base to do day trips from (you could do a day trip from Rome to Florence if you really wanted). 

Planning a trip to Italy? We’d love to help!

Here are our other Italy travel guides to help you plan an incredible trip (even if you have to eat gluten free!).

If there’s no link below, it means we’re still working on it – long, in-depth guides take time! We’re working on it, though, we promise.

If you’re planning a trip and you’re not sure where to start, your first stop should probably be one of our detailed itineraries. 

We have a two week Italy itinerary that blends the main cities with some less-visited cities that we love (BOLOGNA!), a guide to spending 10 days in Italy that focuses mostly on the highlights, and a whirlwind guide to spending one week in Italy that features the Rome – Florence – Venice highlight circuit. 

Here are more specific guides to the main cities in Italy. 




Cinque Terre


The Rest of Italy


  1. Great info, thanks! We are planning a trip next May. Flying to Rome and driving to Pienza for a couple of days, then to Volterra for 3 days ,and then into Florence for 4 and then back to Rome for 4 last days…should be a fun first time trip!

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