Two Weeks in Italy: A Perfect Itinerary for First Timers

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. 

We’ve organized the itinerary below to travel from Rome to Venice (with several stops along the way), which takes you on a tour-de-Italy from Rome to Venice, you’ll want to fly into Rome–Fiumicino International Airport (FCO) and out of Venice 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). 

Getting Around Italy

The best way to get around Italy is by train. At least for your purposes on the itinerary below.

It’s going to be cheaper, faster (once you include travel time and security at the airport), and better for the planet than hopping on a short flight.

There are a few things you should know about trains in Italy before we get any further.

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.

The best way to book train tickets in Italy is directly through Trenitalia, the company that runs most of the trains in Italy. The only downside is that you’ll need to know the name of the station you want to travel to in Italian. 

We’d take high speed trains between Rome and Florence, Florence and Bologna, Bologna and Verona, and Verona and Venice. For day trips from Florence and Bologna, regional trains will do.

Should You Rent a Car in Italy?

For context, we almost never rent a car in Italy, and generally exclusively use the train network. And we always have a lovely time exploring the country.

You definitely won’t need a car in any of the cities. Aside from the stress of driving in a new place, navigating Italian traffic (and drivers), most big cities have a “ZTL” that you can’t enter without a specific permit. Violations – policed by camera – come with a hefty fine.

A car will almost certainly be more of a hindrance than a help in the cities, and the day trips we recommend are very easily accessible using the train. 

However, there are a couple of places where a car might be useful, and they’re add-ons to the main itinerary that we’d only recommend with more than two weeks.

If you’re planning on going deeper into Tuscany (like the Val d’Orcia, Chianti, or San Gimignano), then a car will probably be useful. The same can be said of Sicily (though it depends on what part of Sicily you visit).

Check prices and book on AutoEurope, which is our go-to rental car company in Europe. We used them twice on our three month European adventure – including in Sicily – and it was perfect both times.

The Route for This Itinerary

And now, the itinerary itself. 

One quick note: In general, when you’re moving between cities, we’d recommend taking an afternoon train, which will give you some extra time to explore the city you’re leaving in the morning before heading to the train station.

Here’s how we would plan a trip to see the best of Italy over the course of two weeks, starting in Rome and ending in Venice: 

• Day 1: Arrive in Rome
• Day 2: Rome
• Day 3: Rome
• Day 4: Rome + Train to Florence
• Day 5: Florence
• Day 6: Florence
• Day 7: Florence Day Trip
• Day 8: Train to Bologna
• Day 9: Bologna
• Day 10: Day Trip to Verona
• Day 11: Train to Venice
• Day 12: Venice
• Day 13: Venice
• Day 14: Venice + Fly Home

You’ll notice a couple of different things about the way we’ve structured this itinerary.

First, we’re big fans of spending at least 2-3 days in big cities to avoid feeling like you’re rushing around from sight to sight. That will give you some time to do some exploring to find a new favorite neighborhood, coffee shop, wine bar, or restaurant.

Second, we hate packing and moving accommodations. It sucks. Which is the reason we’re recommending you stay in a place like Florence or Bologna and use it as a home base for exploring the surrounding area.

Third, we’ve included a significant chunk of time in Bologna. Which is our favorite city in Italy not named Rome or Florence (Lucca and Verona are also in the running). 

Here’s why: Bologna is the capital of the best food region in Italy, home to the production of delicious things like Parmesan-Reggiano cheese (we LOVED touring a small producer of Parmigiano-Reggiano with Claudio on this tour), prosciutto di Parma, mortadella, balsamic vinegar, Lambrusco (a sparkling red wine), tortellini, ragu, and plenty more. 

Not only is the food incredible, but the city – which feels noticeably younger and less “touristy” than most of the cities here – is a nice change of pace from places like Rome, Florence, and Venice.

Bologna also makes an excellent home base for day trips because it is so well connected.

Whatever you do, we’d implore you NOT to cut Bologna. It’s an amazing city, and you won’t regret spending a day or two there.

Fourth, it might seem like a lot of time in Venice at the end. However, it’s really only two and a half days if you take a midday train there, and have an early flight home.

If you have a full 14 days in Italy (you’re flying out on day 15, for example), we’d add an extra day either in Florence to do another day trip, or in Rome.

14 Days in Italy: A Perfect Two Week Itinerary for First Timers

And now, on to the detailed itinerary. 

Our intention here is to give you the information we think you need to know to plan an amazing trip to Italy.

We’ll go a little deeper than a short description of each place, giving you some of our favorite things to do, see, eat, and drink that come from our own experiences exploring Italy (and, equally crucially, what not to do – looking at you, Juliet’s House in Verona!). 

We believe those details – like specific wine bars, tours, and coffee shops we loved – are the difference between a good trip and an incredible trip, and hope you’ll find a few places that you wouldn’t have necessarily found on your own. 

The other intention here is to not just give you the same old itinerary that you’ll see in every guidebook.

Of course, we’re going to include Rome, Florence, and Venice, because those are places that are absolutely worth seeing on your first trip to Italy. 

However, we’re also going to include some of our favorite places (like Bologna) that don’t usually make the cut.

Rick Steves (who Matt loves – he’s from Seattle too!) doesn’t even include Bologna in his Italy guidebook! What a miss.  

Rome: Days 1-3

I mean, if you’ve never been to Rome before, you’re in for a treat. Rome is one of our favorite cities in Europe, and there’s something special about walking past architecture from over a thousand years ago on your way to a hip natural wine bar in the evening. 

While Rome is famous for its historical sights, it’s also a great city for food and drinks (as we’ll cover below) and as I’m sitting here writing this, I literally made a Roman pasta dish (amatriciana) for dinner last night. 

We’d recommend three days in Rome, at a minimum, which will allow you enough time to see both of the main attractions, dive into the history of Italy’s capital city, and also indulge in some of Rome’s great food and drinks. 

What to Do in Rome

One of the most important tips we can possibly give you for Rome – though it’s also relevant for just about any city in the world – is to avoid doing multiple big attractions on the same day. 

Speaking as someone who, on a tight timeframe with my mom, tried to do both the Galleria dell’Accademia (home of the David) and the Uffizi Gallery in Florence on the same day, you will absolutely be exhausted by the second one, and you will get far less out of it. 

Part of the reason why we have you spending a fair amount of time in Rome is to give you plenty of time to do the big sights – the Colosseum (and Roman Forum) and the Vatican Museums – on different days. 

Obviously, Rome is a huge, complex, history-filled city, and there is plenty more to experience 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. 

The Colosseum & Roman Forum

The Colosseum and Roman Forum are, perhaps, the greatest example of Rome’s gilded age.

At that point, Rome ruled the Mediterranean, transforming so many places in Europe and North Africa with their innovative technologies (you’ll see big arenas all over, in Spain and southern France, along with things like aqueducts), and created a political system that forms the foundation of so many modern countries. 

You’re not going to want to miss it, and we’d plan on dedicating a half day exploring these two treasure troves of history. 

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. Both are completely free!

Second of all, if you find that you only have the time or budget for one guided tour in Rome, this should be it. 

The reason for that recommendation is that, when you really boil it down, the Roman Forum is really just a bunch of crumbled buildings, and without the added context and history that a guide will bring, it’s hard to wrap your head around what exactly you’re seeing. 

Coincidentally (or not so coincidentally), the guided tour that changed our perspective on whether or not tours are worth it was actually this Colosseum tour with Walks of Italy. 

Before that tour, which shattered some of our misconceptions about the Colosseum and was both educational and entertaining, we were on the fence about whether tours were really worth the price. 

After that tour, we were all in on guided tours, which give you an opportunity to connect with locals, gain a deeper understanding and context for what you’re looking at, and lead to a much richer travel experience, which is what we’re all here for (we think, anyway). 

If you want to know more about that tour, you can read more about our experience on the Colosseum tour that changed our lives (hyperbole, but accurate). 

If you don’t want to do a tour, we have a couple of recommendations for you to make the most of your visit. 

First, buy your tickets in advance – they go on sale a month in advance at the time of the tour (basically to the minute), and by a week or two out your options will be severely limited, especially if you want one of the add-ons, like the underground tour. 

Here is the official ticketing website. 

There are many, many ticket options available, with all sorts of added extras. The basic ticket is the “24h – Colosseum, Roman Forum, Palatine” for €18, which includes admission to both the Colosseum and Roman Forum (which have separate entrances) over 24 hours. 

There are two main additions that you can add that might be worthwhile, depending on what you’re into. 

First is the “Underground Levels,” which gives you access to the maze of tunnels under the arena floor that were used for staging the spectacles. 

Second is the “Attic,” which gives you access to the top floor with great views of the arena. 

You can only choose one, and they cost €24 (but give you access to the Forum for two days instead of one). 

With any ticket, you will book your entrance time for the Colosseum, and then you will have the next 24 hours to do the Forum (we’d do them one after another, maybe with a quick snack or water break in between).

We’d do as early an entry as you can, because it does get HOT in the summer, and there is basically no shade. Another option would be one of the later timeslots, but it is still hot at 3pm. 

Here’s a great guide on Reddit to securing your Colosseum tickets, which I highly recommend giving a read just to be familiar with the process. 

The Vatican Museums & St. Peter’s Basilica

The Vatican Museums (which is where you’ll find the Sistine Chapel) and St. Peter’s Basilica are adjacent, but are two separate entry procedures, so we’re going to talk about them separately. 

Our top tip for this (especially in 2025) is to do them on separate days so that you can enter both at the absolute earliest timeslot you can secure. 

First of all, you’ll need to buy entry tickets for the Vatican Museums, while St. Peter’s Basilica is free to enter. For both, you’ll have to wait in the (sometimes long) security lines. 

The Vatican Museums are home to an absolutely astounding collection of art put together by the Catholic church over centuries.

The Sistine Chapel is the crown jewel of the collection, we’d say, but there are so many sculptures, ornate maps, and various other works of art that are equally impressive to us (we love the hall of maps!).

The challenge with the Vatican Museums is that they are undoubtedly one of the most popular (and therefore busy) tourist attractions in Rome, in Italy, and quite possibly the world. 

Like we said above, we’d strongly recommend an early morning entry if you can get it (though it’s competitive to get those).

A later afternoon entry time will also get you a quiet experience (my guide said usually the afternoon is even more quiet most days), though you’ll be limited by when the museum closes. 

On a recent trip to Rome, I decided to revisit the Vatican Museums after skipping them on the past few visits.

I did the classic early morning “Pristine Sistine” tour with Walks of Italy, the same company who ran that life changing Colosseum tour, and very much enjoyed it. 

However, due to changing rules and regulations with the Vatican, you should know that you are very much not alone in the Sistine Chapel anymore. 

For that experience, you need to splurge on the Key Master’s Tour, which is significantly more expensive BUT has you literally unlocking the door to the chapel first thing in the morning, which is probably a once-in-a-lifetime experience that you won’t soon forget. 

If the tour isn’t in the budget (or you would prefer to go at your own pace), this is another place that you should definitely buy tickets for in advance, especially during the summer.

Buy tickets here – toggle the site to English with the language selector in the top right. 

They go on sale 60 days in advance, and sell out within an hour if it’s peak season. You want those early entry times!

For the best experience, we’d recommend picking the tickets that include an audio guide.

It’s a good middle ground between visiting independently and on a guided tour that gives you more information and context, but also allows you to move at your own pace. 

For St. Peter’s Basilica, which is free to enter, we’d recommend going first thing in the morning when it opens (7am at the time of writing) to avoid the LONG security lines which wrap all the way around the square later in the day.

It’s free to enter, but you do need to wait in that line. 

It’s also worth climbing the dome of the basilica, which is not free, which opens at 7:30am. 

A few tips for visiting the Vatican Museums and St. Peter’s Basilica: 

• It’s a lot of walking, including stairs. I clocked ~10,000 steps along the way, including several sets of stairs. If you have mobility restrictions, that might be a lot of moving around. 
  
  
• You must cover your knees and shoulders inside St. Peter’s Basilica (it’s a Catholic church after all), so leave the short shorts and tank tops at home for this day, otherwise they will not allow you to enter.
  
  
• There is no photo or video allowed inside the Sistine Chapel. Yes, there are guards. No, you shouldn’t try to sneak a photo. Be respectful! 

The view from the Orange Garden (Giardino degli Aranci)

This is one of our favorite views in the city, and we’re not alone. Head up here around sunset for a treat, but it’s equally gorgeous in the early morning hours (perhaps better, because the sun is generally behind you), and there are far fewer people.

Experience the Magic that is Trastevere in the evening

Our favorite neighborhood in Rome is Trastevere, and it’s not that close.

It’s nice in the morning, especially if you visit the open air market that takes place at Piazza de’ Renzi, but the evening is when it comes alive. People spill out of the bars and restaurants into the streets, and the piazzas are full of people drinking and being merry. 

Drink Plenty of Italian Wine!

Enoteca il Piccolo in the Centro Storico (here it is on Google Maps) is as great as it is popular.

The owner came out to the terrace where I tried to explain in my bad Italian what kind of wine I wanted (dry white), and he walked away without a word, and returned with two excellent glasses of exactly what I asked for.

If you’re looking for a bottle, Les Vignerons in Trastevere is the place to go (great beer and cider selection, too!). 

Explore Roman cuisine

First, we make the four Roman pastas at home (carbonara, gricia, amatriciana, and cacio e pepe) all the time. Roman food is generally very simple, but delicious.

The best way to learn about Roman food is taking a food tour with a local guide, where you’ll not only taste some delicious food, but learn about the history and context behind that food. Which is our favorite part about learning about food cultures of different places.

We’d do this tour, which looks truly spectacular and includes a lot of cultural context along with tons of tastings. 

If you’re into good coffee, head straight to Pergamino Caffè near the Vatican, which is home to some of the best baristas in Rome who bring in a bunch of different Italian specialty coffee roasters to brew for you.

It’s my, Matt the coffee snob’s, favorite coffee in Rome. 

Of course, there are tons of other things in the Eternal City that are worth doing, seeing, and eating. For more, head over to our guide to the best things to do in Rome, which has a collection of our favorites. 

Where to Stay in Rome

While there are a bunch of areas you could stay in Rome, we have two strong recommendations for you to help you narrow it down.

We also have an entire, super detailed guide to where to stay in Rome if you want more details to make your decision.

Our overall recommendation is to stay in Trastevere, which is far and away our favorite part of the city.

We stayed there on our last trip, and it’s magical.

It’s a great place to eat and drink, and it really comes alive when the sun goes down, full of lively piazzas and small bars and restaurants that fill up on a nightly basis and spill out into the cobblestone streets.

We stayed at Horti 14 Borgo, a small boutique hotel in Trastevere, and absolutely loved it.

It’s a splurge compared to where we normally stay, but the stylish rooms, comfortable beds, and incredible breakfast buffet were worth it. 

A more affordable (but equally highly rated) option would be Ripagrande a Trastevere, which is essentially right on the River Tiber and within five minutes of everything in Trastevere. 

The only downside to Trastevere is the fact that it’s a little far from the train station, which doesn’t matter as much with three days, but is a little less convenient (you’ll need to take a taxi, most likely).

Which brings us to our second recommendation, which is Rome’s Historic Center (the Centro Storico). 

Stay here if you want to be right in the middle of all the action, within walking distance to just about everything in the city.

It’s the most convenient place to stay, though it will be crowded and potentially loud. Don’t miss an early morning walk from Piazza Navona to the Trevi Fountain and the Spanish Steps!

We stayed for five nights near Piazza Navona at these apartments, which were honestly a perfect location, especially if it’s your first time in Rome.

Coronari Palace and Casa Pietra are two hotels that were also on our list, though we decided we wanted more space and a kitchen for our time in Rome. 

Florence: Days 4-6

Historically, the city of Rome might be the crown jewel of the Roman Empire, but you could make a convincing argument that Florence is the second most important city in the history of the Italian peninsula because of its influence around the birth of the Renaissance. 

On a walking tour in Florence (this one, which we recommend below because it’s a great introduction to the city), as we were walking through Piazza della Signoria, our guide made a point that I hadn’t really thought about before that moment. 

Florence was one of the richest cities in Europe (if not the world) in the 15th Century and through the Renaissance. 

A lot of people – myself included – might think that wealth came from the amazing art that was produced in Florence leading up to and during the Renaissance.

But the truth is that Florence was already a rich city thanks to silk production, and that wealth is what allowed it to become a cultural icon that thousands of people still flock to five centuries later. 

Walking the streets of Florence, it’s easy to see why so many people fall head over heels in love with it on their visit.

It’s charming. The Duomo is incredible, both because of how imposing it is, and the fact that it’s an architectural miracle. There are two world class museums.

The food and wine are both excellent (definitely get the wild boar if you see it on a menu – pappardelle al cinghiale – which was our favorite discovery on our Tuscany road trip itinerary). 

I could go on and on about Florence – I’ve spent over a week in Florence between two trips in the past year (at the time of writing) – but let’s leave it there and get into how to make the most of your time in the Tuscan capital. 

In this itinerary, we have you spending two and a half days in Florence itself, and then using it as a home base for a day trip into Tuscany. 

What to Do in Florence

In Florence, we think a couple of days is enough to see the highlights, and there are so many great possibilities when it comes to day trips from Florence that we think you should spend one of your days here outside of the city, experiencing a different slice of Italian life (and we have suggestions and opinions!). 

Obviously, Florence is a cultural and historical gem, and there is plenty more to expereince.

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

Here are a few of our favorite things to do and see in Florence. 

The Uffizi Gallery

Of the two main museums in Florence, the Uffizi Gallery is BY FAR our top pick. 

Yes, the David is a masterpiece, and the other works in the Galleria dell’Accademia that show you how Michelangelo’s relentless pursuit of understanding the human body led to the creation of the marble masterpiece. But we’ll talk about that in the next section. 

What we really love are art museums that tell a coherent story, either about the place they’re located (the National Portrait Gallery in London), a specific movement (the Musée d’Orsay and Impressionism), or a specific artist (the Rodin Museum in Paris). 

Similar to the Musée d’Orsay in Paris, which tells a compelling story about how the bad boys of Impressionism shirked conventional wisdom and forged their own path that later became one of the most iconic movements in art history, the Uffizi Gallery tells a story about the painters of the Renaissance that is inherently intertwined with the history of Florence. 

A lot of people, us included, assume that Florence became a wealthy city because it had all of this beautiful art.

But the truth is actually the inversion of that statement – Florence was able to commission all of this gorgeous art because of its immense wealth, which was required to commission the famous artists of the Renaissance

The Uffizi Gallery is a chronological walk through time, starting with the period immediately before the Renaissance, where you had people mostly painting Jesus in two dimensions with a golden halo around his head, to the end of the Renaissance, when people were painting life-like figures in three dimensions that looked like real humans. 

As you might imagine, we have been to the Uffizi Gallery multiple times, first on our own, then with the audio guide, then on (multiple) guided tours. 

It wasn’t until the first guided tour we did (here is that tour) that we truly began to grasp what exactly we were seeing; a revolution in the art world that began and flourished in Florence. 

We’d strongly recommend a guided tour here, and would rank it as the second historical/museum tour to do on this itinerary after the Colosseum because the story of the Renaissance really requires a bit of extra explanation and context. 

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. 

If you’re not going to do a guided tour, you’re going to want to book your tickets for the Uffizi Gallery well in advance, and plan the rest of your time in Florence around that timeslot. 

This is the official website of the museum, and similar to the Vatican Museums, you’ll want to either book the first few timeslots of the day (what we’re doing on an upcoming trip to Florence) or a later afternoon timeslot, when the museum tends to be a little bit quieter. 

You’re also going to want the audio guide, we think, if you’re not doing a tour. It’s a good middle ground between a tour and just wandering the museum on your own. 

The David & the Galleria dell’Accademia

As we’ve already mentioned, the David is a masterpiece.

Cut out of a single piece of marble, it stands 17 feet tall (taller because it’s elevated on a pedestal the way it’s displayed) and towers above you in the Galleria dell’Accademia (where it is now housed). 

It used to be out on Piazza della Signoria, but was moved inside to protect it from the elements.

There is still a replica out on the piazza, along with another version up at Piazzale Michelangelo (which is a great view of Florence). 

Many people come to this museum just to see the David, though we think it’s worth taking an extra second to stop and learn about Michelangelo’s process and how his brain worked, because I found it fascinating on my last visit. 

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, where you can walk all the way around it, is also cool). 

However, if we had to choose one museum to do in Florence, we would not hesitate for an instant to point you to the Uffizi Gallery.

If you only have time or interest in one, do the Uffizi and go see the replica in Piazza della Signoria on your way in. 

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 offers a great overview of the story of Michelangelo and his career leading up to the David. 

Take Andrea’s walking tour

We’re huge fans of walking tours as a way to get an introduction to a new city and connect with a local for tips on what (and where) to eat, drink, and shop.

And we loved Andrea’s walking tour, which is a two hour crash course in Florence’s rich history, with all the salacious details about the Medici family (they were essentially royalty in Florence during the 1500’s).

He also has a more in-depth version of the tour that adds an hour and includes crossing the river to Oltrarno. 

Climb to Piazzale Michelangelo

On the other side of the river from Florence’s Centro Storico, you’ll find what is arguably the best view of the city at Piazzale Michelangelo.

You’ll have a view of the Arno River and Ponte Vecchio (the only bridge in Florence that wasn’t destroyed in World War 2), the Duomo, and the rest of the city.

It’s nice at sunset, but it’s busy. Early in the morning is even better, because the sun is behind you and there are basically no crowds. 

Climb Brunneleschi’s Dome

The Duomo in Florence is massive. The best way to experience it, in our opinion, is to climb to the top.

Along the way, you’ll get a view of the interior of the dome and the (somewhat creepy) artwork decorating it, then you’ll climb through the area between the interior and exterior dome (which gives you perspective on how it was built 600 years ago, which is mind-boggling) up to the top, where you’ll have a 360-degree view out over Florence.

Try to do it first thing in the morning for the fewest people, and book in advance here. 

Dive into Tuscany’s food and drink offerings

We’d strongly encourage you to skip the pizza in Florence, and instead indulge in some of the local specialties.

We love Pappardelle al ragu di cinghiale (a pasta with a wild boar sauce that my mom fell in love with), pappa al pomodoro (tomato and bread soup), and the Schiacciata (sort of like a focaccia sandwich, but slightly different).

We liked the food at Trattoria da Garibardi.

Most of the Florentine cuisine pairs well with the Tuscan reds like Chianti Classico and Brunello, which are a couple of the more prestigious red wines to look for. 

Where to Stay in Florence

Similar to Rome above, we have two recommendations for where to stay in Florence.

Also similar to Rome, your choice is going to be between the coolest neighborhood (in our opinions, anyway) and the most convenient area.

Convenience matters a little more here because you will be taking a day trip, which means you’ll be going to and from the train station.

Our favorite area in Florence is Santa Croce / Sant’Ambrogio, which is a five minute walk east of the Duomo. It has the best food (we think), fewer tourists, and is close to everything in the city.

We stayed at Pietrapiana Boutique Apartments for almost a week, and it was everything we wanted and more: access to a kitchen, a little more space to spread out, a quiet refuge from the hustle and bustle, and a comfortable place to sleep. Highly recommend! 

La Maison du Sage is another good option nearby – it’s more of a traditional hotel than serviced apartments.

The other option, which is best if you want to be super central to everything in Florence, is Florence’s Centro Storico, which is centered around the Piazza del Duomo and nearby Piazza della Signoria (home to the Uffizi Gallery).

It’s crowded, it’s loud, but it’s super convenient. It’s also closer to the train station for your day trip.

Day Trip from Florence (Choose Your Own Adventure): Day 7

Florence is the capital of Tuscany, which might be Italy’s most famous region for its wine and general dolce vita feeling. And, after spending a week in Tuscany, we can definitively say it delivers on both. 

Florence is an excellent base to explore Tuscany from, with most of the highlights accessible within 90 minutes by train. However, the main issue with Tuscany is that you really need a car to be able to see certain things properly.

Here are the three day trips from Florence we’d recommend, and which one you choose totally depends on what you’re interested in. 

If you’re looking to combine San Gimignano, Chianti, and Siena into one day, it’s going to be a long day, but this tour with Take Walks (which, as we’ve already mentioned a few times in this guide, is one of our favorite tour companies on earth), covers San Gimignano, Chianti, and Siena in one action-packed 10 hour day. 

Bologna: Days 8 & 9

You’re probably a little bit surprised to see Bologna on this itinerary, since it’s not exactly known as one of the “must-see” cities in Italy. However, we’re here to tell you that it absolutely should be on your list, particularly if you love food. 

One of the most interesting parts about traveling to Italy is having our expectations about “Italian” food completely shattered.

Here in the US, Italian food (we now know that Italian–American food is an entirely separate thing) consists of heavy sauces with lots of garlic, garlic bread, and chicken parmigiana. 

The truth is that Italian food culture is vastly different from region to region, and depends a lot on the fresh ingredients available in close proximity.

For example, in Sicily, you’ll find tons of fresh seafood because you’re on an island and are perpetually near the coast. In Tuscany, it’s olives, wild boar, and sheep cheese (pecorino) because those are the ingredients that are readily available. 

If you made us choose our favorite Italian food region, we’d choose Emilia-Romagna, which is where you’ll find Bologna. 

Here’s an exercise: write down your five favorite Italian ingredients (rather than dishes). If you’re anything like us, at least one of the things you wrote down comes from Bologna’s region, Emilia-Romagna. 

There’s a reason the city is known as “La Grassa” (“the fat one”). It’s about as close to heaven for foodies as you can get. 

There are, of course, other things we really like about Bologna. It’s a city of towers that overlook the distinctive red brick buildings (most of them are facades, though).

It’s a University town (one of its other nicknames is “La Dotta” which means “the learned one”) and it has a distinctly younger vibe than just about any other major city in Italy. There are far fewer tourists than any other city you’ll visit.

And it’s well connected to just about every corner of Italy. 

We think you should spend three nights in Bologna, using one of those nights to do a day trip up to Verona, which is another one of our favorite cities in Italy. 

What to Do in Bologna

Here are a few of our favorite things to do in Bologna. For more, head over to our guide to spending a day in Bologna. 

Climb the Asinelli Tower for Excellent Views

We have friends that live in Bologna, and when we visited them on our first ever visit to Bologna, this was the first thing they did with us.

It’s a big climb, but you’ll eventually end up on the top of the taller of the Due Torre (“the two towers”), where you’ll have a commanding view out over Bologna. Book here in advance for a timeslot. 

Eat your heart out

Mortadella and filled pastas like tortelloni come from Bologna, but the broader region is home to just about every delicious food we associate with Italy.

Parmesan, balsamic vinegar, prosciutto di Parma, lambrusco, and ragu alla bolognese.

Go to any of the places in Quadrilatero, which is right off of Piazza Maggiore, to taste and shop.

Specifically, we like Tamburini for tagliere (a plate of meats and cheeses) and a glass of wine (lambrusco!), Cremeria la Vecchia Stalla for excellent ice cream (which is NOT the same as gelato), and Vineria Favalli for their excellent Italian wine list.

Take a food tour with a local guide

While you can absolutely get a sense for Bologna’s food offerings on your own, a food tour is going to be the best way to dive a little deeper.

This food tour in Bologna was on our list, but after learning they couldn’t accommodate gluten free diets (which, by the way, makes total sense), we decided to skip it. 

Take in Piazza Maggiore and Basilica di San Petronio

Piazza Maggiure is the beating heart of Bologna, and one of Italy’s best piazzas in our opinion (as we noted above, Siena’s Piazza del Campo is a close second).

There are events nearly every afternoon and evening, from rallies to concerts, and even when there isn’t an official event, you’ll find some of Bologna’s best musicians out on the square (along with a crowd of admirers).

The church is worth going into, but it’s only half finished after they tried to make it outshine the Vatican, who said “you can’t do that.”

That’s why part of the church’s facade is exposed brick, which is the unfinished portion, while the other part is covered in marble.  

Make the climb to Santuario Madonna di San Luca

Bologna is known for porticoes, which are essentially just covered walkways, and you can walk through the 666 (someone has a sense of humor) to get up to this church on the hill.

For what it’s worth, this the #1 recommendation from our friends that live in Bologna. 

Where to Stay in Bologna

There’s no doubt in our minds – you should stay near Piazza Maggiore while you’re in Bologna. It’s the beating heart of the city, and it’s going to be both the most convenient and the coolest place to stay.

I spent a few days in Bologna solo on my last trip to Italy, and stayed at Bibliò Rooms and Guesthouse. It’s essentially a small B&B that takes up one floor on a residential building about five minutes from Piazza Maggiore.

The rooms are fairly spacious with comfortable beds and private bathrooms, and it’s a good home base for a few nights in Bologna. 

I also stayed at the Social Hub in Bologna, which is a hip, young-feeling hotel in Bolognina up near Bologna Centrale.

While the location is further away from Bologna’s main attractions, it is a gorgeous hotel with all sorts of great amenities (a pool, a nice gym, a bar, an events calendar, and ping pong, to name a few). Plus, it’s about five minutes on foot from the train station, so it’s convenient in that sense. 

If you’re looking for an apartment, look at Canonica Suites, which is where I kind of wish we had stayed. 

We have an entire guide dedicated to helping you figure out where to stay in Bologna with FAR more detail, if you want more of an in-depth look at your options.

Venice: Days 11-14

Venice is a place that we have mixed feelings about. We’ve both been to Venice, and as we’ve thought about it, we’re truly not sure if we need to go again. 

It’s true that Venice is the best-preserved example of a canal city in Italy, but it’s also true that it’s a beautiful disaster.

There are way, way too many people trying to see Venice for the infrastructure to handle, and cruise ships are a big part of the issue, with huge tour groups coming in for part of a day and contributing very little to the local economy while stressing Venice’s infrastructure. 

Remember in 2020 when the canals were all of a sudden empty and pristine, and the swans came back to Venice? It’s safe to say that’s over now. 

However, it’s not really fair to say that you shouldn’t get to see Venice because too many people go there. 

Instead, we’d recommend that you do go to Venice, but be deliberate about how you do it.

Spend multiple days there so you’re not stressed about the crowds and whether or not you’ll be able to do everything. Eat at local restaurants, and stay in Venice so that your money stays in the local economy. 

The best way to explore Venice is not to spend a day (or less) seeing the main sights and calling it a day.

Venice is at its best in the early morning and evening, when it’s notably less crowded. If you only spend a day in Venice, you’re likely going to miss out on that precious time spent exploring during those hours. 

That’s why we’d strongly recommend two and a half days in Venice, which gives you a couple of mornings and nights to really soak up the atmosphere of Venice when it’s not packed wall-to-wall with people. 

What to Do in Venice

There are a few main sights in Venice that you shouldn’t miss, and two days is more than enough time to see them. Like we said above, part of the fun of exploring Venice is wandering the canals in the early morning and evening. 

Piazza San Marco is the main piazza in Venice, and there are a couple of main sights right on the square. 

First is the Doge’s Palace, which is a big Gothic building (you know because of the pointed arches) on the lagoon. Over its long history, it served as a fort, a prison, and a residence for the most powerful person in Venice, the Doge. 

The version you see today was built in the 1100’s, and has been renovated a few times since as the needs of its inhabitants changed.

It housed the Doge of Venice (sort of like a Duke, but not quite the same) during the Republic of Venice, which lasted for more than 1,000 years starting in the 8th Century and was one of the most powerful city-states in modern day Italy for long stretches because of its position on the water.

The best part about the Doge’s Palace is that it’s an excellent place to learn about Venice’s history. For example, I had no idea that there was a Republic of Venice, let alone how powerful they were.  

You can buy your tickets in advance here. 

The second major attraction on San Marco Square is the church, St. Mark’s Basilica (Basilica di San Marco), which is the biggest church in Venice.

In a surprising (to no one) twist, the church is attached to the Doge’s Palace, showing the relationship between secular and religious power in Venice over the centuries.

It’s set on the site of two older churches, which is a story that you hear over and over again at some of Italy’s biggest and most important churches.

Also similar to other churches in Italy, it was built over such a long stretch of time that it’s one big mish mash of architectural styles and art periods. 

It’s an impressive building from the outside, and the interior is special because of the mosaics that cover just about every surface. The Pala d’Oro, which is essentially a big golden altarpiece from the Byzantines, is also pretty cool. 

Information on tickets and opening hours here. 

If you want to see both with a guided tour, we’d (again) recommend doing the St. Mark’s and Doge’s Palace tour with Take Walks, who we’ve done multiple tours with in multiple Italian cities, and love.

It’s three hours long, includes both the church and the palace, and will take you a level deeper than just visiting by yourself. 

The islands to the north of Venice – namely Burano and Murano – are well worth a visit, and the vast majority of visitors don’t make it out there.

These tiny islands are known for glassblowing, and they’re relatively easy to reach via water taxi from Venice. From this ferry terminal, it’s a quick 20 minute ride over to Murano, the closer of the two islands (it’s a significantly longer boat ride out to Burano). 

You can read more about what to do in Venice in our guide to spending 2 days in Venice. 

What to Do with More Time in Italy

If you’re blessed with more time in Italy, we have (lots of) thoughts on what to do with extra time. Whether it’s one or two days or a full extra week, we have ideas for you based on our own explorations. 

Keep in mind that this isn’t an exhaustive list – we haven’t been everywhere in Italy, and it’s hard to recommend something we haven’t experienced ourselves.

For example, the Dolomites and Lake Como are on our list, but we didn’t include them below. Once we make it there, we’ll definitely add them!

You’ll notice that there’s one very popular destination missing from this list that you might be expecting to see: Naples, Pompeii, and the Amalfi Coast.

We contemplated adding it because we know it’s a place that people have seen pictures of and want to visit, but we really wouldn’t do it ourselves due to insane crowds and associated overtourism. 

Just this last summer, we’ve seen about 30 pictures of friends on Instagram who all went to the Amalfi Coast within the same two month period. 

Which, when you take a second to think about it, is pretty crazy. 

We think there are better coastal destinations in Italy (like the Cinque Terre – which has its own over tourism issues – and Sicily) that we’d recommend way before the Amalfi Coast. You’ll find both of those on the list below. 

Add Another Day Trip from Bologna 

The first thing we’d add if you only have an extra day or two is an extra night in Bologna to explore more of Emilia-Romagna.

Cities like Parma (famous for prosciutto and parmesan-reggiano) and Modena (famous for balsamic vinegar) are an easy train ride away, and are well worth your time. 

We’d then spend the rest of the day in Modena, which is the capital of balsamic vinegar production and is an easy 20 minute ride from the train station in Reggio-Emilia (where you’ll get dropped off by Claudio). That’s what we did. 

We loved tasting small production balsamic vinegar at La Consorteria 1966 (you should know that the tasting costs money unless you buy a bottle afterwards, which are expensive because this is the good stuff). 

We also had multiple people recommend Osteria Francescana, which is a world-famous fine dining experience that you’ll need to book well in advance.

You can also try chef Massimo’s food at nearby Franceschetta58, which is less expensive and more approachable (you still want a reservation, though!). 

Another great stop is the Mercato Storico Albinelli, which is Modena’s central market. 

Cinque Terre (2-3 Days)

For my mom’s 60^th birthday, we took her on a two week trip around Italy. Her two must-do experiences were the Cinque Terre and seeing the Last Supper in Milan.

So, we spent a few days exploring the Cinque Terre, and we loved it.

However, we have a major caveat. We would absolutely NOT recommend a day trip to the Cinque Terre, which is what approximately 90% of people seemed to be doing.

The main reason is that it’s a long way from places like Florence and Milan, requiring three hours of travel time.

That means you won’t arrive until mid-morning, which is when all of the other day trippers arrive, and the streets and trails are packed wall-to-wall. It’s no wonder people say it’s too crowded!

The magic of the Cinque Terre is in the early morning and late evening, when the day trippers clear out and it becomes a tranquil, slow paced coastal retreat. That means you’ll need at least one night (two or more is better).

The Cinque Terre, which literally means “Five Towns,” is a series of charming towns tucked between the mountains and the coast in northern Italy.

It’s known for hiking, terraced vineyards, and colorful towns perched on rocky outcroppings above the sea.

Milan (2 Days)

Milan is a really great city that offers something a little different from other major cities like Rome and Florence.

That’s not to say that it’s not a historic city, but it feels less “Italian” than Rome and Florence mostly because it has been trading hands between the Spanish, French, Italians, and Austrians for centuries.

There is a difference that you’ll notice right off the bat, probably when you exit the train station.

It looks and feels more modern, which is mostly a function of the fact that it’s a major financial hub and home to just about every high end fashion company in the country.

There are two world-class attractions in Milan – the Duomo di Milano which took 600 years to complete and is a mishmash of different styles that somehow still works, and Da Vinci’s Last Supper.

However, it’s worth lingering for an extra day to explore some of Milan’s less famous attractions and the hip food and drink scene.

Wander Parco Sempione and pop into Castelo Sforza, and experience aperitivo in the Navigli District, which is home to some of Milan’s last exposed canals (it used to look like Venice!). 

Sicily (7 Days)

If you have about a full week of extra time, we’d highly recommend exploring Sicily.

We love Sicily (Alysha’s family is from a small town in southeast Sicily), and spent three weeks on the island in the fall (which somehow was still not enough time). 

However, you should know that Sicily is massive, and it’s impossible to do the entire island in a week.

For that reason, we’d focus on southeastern Sicily (Catania, Mount Etna, and Syracuse). Unfortunately, that means you’ll miss Palermo, which is an amazing city in northwestern Sicily.

The other reason to focus on southeastern Sicily is that you don’t need to rent a car. The corridor from Taormina to Syracuse is connected by a regional train line, which is something that can’t necessarily be said for the rest of the island.

To get there, you’ll need to fly. The best place to fly into is Catania (Catania–Fontanarossa Airport).

Definitely don’t miss a day trip from Catania up to Mount Etna, which was among the highlights of our trip (you can read about it in our guide to the best things to do in Catania) and a trip to the amphitheater in Taormina, which has a spectacular view.

Oh, and eat all of the pistachio and almond granitas you can. 

We have an entire guide dedicated to helping you plan a Sicily itinerary, which has a couple of ideas for how to spend 7 days on the island (P.S. we recently wrote a specific guide for spending 7 days in Sicily, which is even more helpful and specific in this context).

Where to add it: We’d add it after Venice, flying from Venice to Catania (which might require a connection) and flying home from Catania.

What to Do with Less Time in Italy

We’re not going to dive deep into how to spend less time in Italy, mostly because we’ve already done exactly that in some of our other guides. 

We have a guide to 10 days in Italy that’s geared towards first-timers that focuses on Rome, Florence, and Venice, and how to make the most out of your time in those places. 

We also have a guide to spending 7 days in Italy, which is a little different because it gives a bunch of different ways to do a weeklong trip to Italy. 

If you’re looking for ideas for a shorter trip, definitely read those.

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