Five Days in Italy – The Ultimate Itinerary

Italy has so much to offer & it feels almost impossible to put together the perfect Italy itinerary, because you could spend 100 days there and not see everything worth seeing! But, since that’s not really an option for most of us I decided to take a stab at putting together a shorter five day itinerary. This is a great itinerary if you don’t have a ton of time, or Italy is a part of a larger trip to other countries, like France or Greece. Five days gives you enough time to seethe most iconic cities in Italy!

My main recommendations for a five day trip would be Venice, Florence (with optional day trips to Tuscany) and Rome Keep reading below for details on getting around, how long to spend in each place, and more!

If you have more time to explore Italy check out my seven or ten day itineraries!

Disclaimer: This article contains some links where I earn commission through booking. There is no extra cost to you, and I only recommend things I’ve used and love or places I’ve stayed and enjoyed!

Day 1: Venice

Venice is such a unique city, and for me, it’s a must see on a trip to Italy. I recommend starting in Venice (which is located in the Northeast part of Italy) and then making your way South during the remainder of your trip. Venice is a smaller city that can be seen and experienced in a shorter time frame than some other Italian cities, which is why I recommend just one day in Venice! Not that it isn’t worth spending more time there, but with there being so much to see in Italy I think one day in Venice is enough to see everything you’d want to see!

Getting There

Venice is accessible via plane or Italy’s extensive train system. Venice Marco Polo Airport is an international airport and about a 20 minute drive from downtown Venice. The main train station, Venezia Santa Lucia, is located right in the heart of Venice.

Where to Stay

Venice is made up of mostly small winding paths and bridges that cross the many canals. This can make it tricky to navigate, especially with luggage, as you cannot simply hop in a taxi to get to your hotel. I recommend staying at a hotel is easy-ish walking distance to the main train station (especially depending on how much luggage you have)

Luckily, this puts you right on the Grand Canal, giving you tons of great hotel options and those picturesque Venice views! I recommend CHC BW Continental or Hotel Carlton on the Grand Canal, but you can find tons of hotel options across budgets in that area. Also, staying along the main canal makes it easier to find your way back to your hotel after a day or exploring (and some wine) the winding streets can lead to getting lost easily!

What to Do

My personal favorite part of Venice is getting lost wandering through the dreamy streets. There are endless photo opportunities of little bridges spanning the various canals. I really think Venice is meant to be wandered, as opposed to having a structured itinerary with lists of things to see. But you’ll certainly want to explore:

• Piazza San Marco & the Basilica di San Marco, which is the main square of Venice.
• The infamous Rialto Bridge, which is one of the many bridges spanning the Grand Canal is also a can’t miss, but you’ll almost inevitably stumble across it during your exploring!
• A gondola tour is certainly the quintessential Venice experience, but they are very pricy. But the public Venice ferry system is also a cheaper option if you just want to get out on the canals!

Days 2: Florence

I say this a lot on here, but Florence is undoubtedly my favorite city in the world, so take my advice with a slight grain of salt! But Florence is an absolute must see on your Italy trip. It’s a walkable, stunning city with tons to offer for any tourist, but it’s also small enough to see the highlights in a short time if that’s all you have! One of the best parts of Florence is how conveniently it’s located for day trips to places like Tuscany.

I recommend spending two days in Florence, and dedicating a half day (or so) to exploring some of the great spots accessible to Florence. This means you don’t need to drag your luggage with you on these day trips and you don’t need to check in and out of multiple hotels! Below is an overview of my Florence suggestions, but check out our full Florence travel guide for more suggestions!

Getting There

The main train station in Florence, Santa Maria Novella, is conveniently located in the heart of Florence. There are high speed trains running from all major large cities in Italy many times a day, so you can catch a high speed train from Venice to Florence. Florence also has a small airport, but it’s easier to fly to Italy into one of the major airports, like Rome, Venice or Milan.

Where to Stay

Florence is a a fairly small city, so no matter which area you choose to stay in you’ll be less than a 20 minute walk from almost any other area of the city. There are a ton of hotel options in addition to hundreds of rental properties, so finding your ideal location and price point should be possible. I’ve stayed in Florence mostly on longer term trips so I’ve opted for VRBO’s most of the time, but I’ve also stayed at a few hotels and have included recommendations in each area.

Piazza del Duomo:

The Duomo is the center of Florence, towering over the city. You can catch glimpses of the massive dome from many different streets and areas of the city. If you want to be right in the heart of the action, staying in Piazza del Duomo is a great option. A few hotels I’d recommend: Granduomo for the views, Hotel Cerretani for a more modern hotel, Palazzo Niccolini al Duomo for a charming Renaissance vibe or Guest House Bel Duomo if you’re looking for a lower price with an unbeatable location! VRBO also has tons of options near the Duomo!

Piazza della Signoria (Palazzo Vecchio):

Palazzo Vecchio (or the old Palace) is only about a 5 minute walk from the Duomo, but is another great option for where to stay when visiting Florence. The square is always lively and has tons of restaurants and bars overlooking Palazzo Vecchio that are great for an aperitif! I stayed in this area for about 3 weeks during my last trip to Florence and loved the location! My stay at this VRBO was incredible and I would recommend it to anyone interested in being in this area. There are also some great hotel options, like, San Firenze Suites & Spa for the views, or for a more cost friendly option, Hotel Renaissance.

Oltrarno:

Now that I’ve spent a significant amount of time in Florence, the Oltrarno (literally meaning “other side of the river”) is my favorite neighborhood. It right across the Ponte Vecchio, and is still close to the Duomo & train station, but I find that it has a bit more of an authentic feel. And some of my favorite restaurants, and spots in Florence are in the Oltrarno area of Florence. My top recommendations would be Hotel Pitti Palace Al Ponte Vecchio (that terrace view alone is enough of a selling point) Hotel La Scaletta is also a nice option and a bit cheaper. If you’re looking to splurge 10/10 recommend would recommend Hotel Lungarno. There are fewer hotels on this side of the river, but there are plenty of VRBO options

Ponte Vecchio:

The Ponte Vecchio is my favorite thing in Florence. I never knew I’d be so enchanted by a bridge! But it is absolutely stunning at all times of day. It’s a great place to stay to be right by the Arno and easily cross the river, but also still really close to the Duomo and Palazzo Vecchio! The hotels in this area tend to be a bit on the pricy side, but the view and location are unbeatable! Some great options are Hotel Hermitage, Hotel Continentale & Hotel degli Orafi

Explore Florence

I’d recommend spending your first day exploring the city. I’ve compiled a list of some of the best things to do in Florence, but it would be a lot to squeeze into one day. My top recommendations are climbing the Bell Tower or the Duomo, Piazzale Michelangelo for sunset, wandering across the Palazzo Vecchio, & checking out Michelangelo’s, The David at Galleria Academia

Duomo:

The Duomo consists of four parts – the cathedral, the main church the duomo sits on top of, Brunelleschi’s infamous Duomo ,the dome you can take a tour of, the Baptistery, a standalone building next to the cathedral, and Giotto’s Bell Tower. You can visit all four of these, or pick which ones you’d like to see. The Cathedral is free and does not require a ticket – be warned the lines get long. The other three require a ticket for entry and you’ll need to select a time. Depending on what you want to do there are multiple ticket options.

Personally, I don’t think you need to climb the Dome and the Bell Tower, but that is an option. If you’re choosing between the two – I think the view from the Bell Tower is better, because you get to see the cityscape as well as the Dome up close, but if you’re interested in seeing the artwork in the dome up close you’ll want to choose that option. There are also skip the line and guided tour options!

Ponte Vecchio:

The Ponte Vecchio (or Old Bridge) is one of the most famous landmarks in Florence. You don’t need tickets or anything, it’s simply somewhere you must see in Florence! As you walk across the bridge it is lined with jewelry shops on either side for those looking to splurge! Also, make sure you check out the views of the Ponte Vecchio from the bridges on either side.

Michelangelo’s David:

The David really is a can’t miss experience. It’s hard to explain why it’s so impressive when you see it in person, but it really is breathtaking. It’s located in the Galleria del’Academia. I’d definitely recommend you book your tickets in advance, you don’t need to, but the line is always super long for people waiting for tickets. Tickets online through their site are 16 euro, but you get to skip the line by selecting a time. These sell out so definitely get them in advance. If they are sold out you can get tickets on Viator or book a tour to get access

Palazzo Pitti + Boboli Gardens:

I definitely recommend a trip to the Boboli Gardens. They are part of Palazzo Pitti (the new palace the Medici’s built across the Arno) You can tour both the Palace and the Gardens or just one or the other. The gardens are massive and you can spend hours walking around. The gardens are also a great way to get a glimpse of those stunning Tuscan country sides if you don’t have time to venture to Tuscany on your own. You can buy tickets online or opt for a skip the line or private tour with Viator

Palazzo Vecchio:

Palazzo Vecchio (or the old Palace) towers over Piazza della Signoria and it’s definitely worth exploring from the outside, even if you don’t buy tickets for the inside. The inside has three separate areas (the tower, the wall and the museum) you can buy individual tickets for each, or a combo ticket if you’d like to do all three. If you decide you’d like tickets beware of really long wait times during peak tourist times. Tickets can be purchases ahead of time on Viator

Sunset at Piazzale Michelangelo:

Piazzale Michelangelo is an absolutely can’t miss Florence spot! It’s a large piazza overlooking the entire city and offers the best sunset spot in Florence. Sit back on the stairs with a bottle of wine (you can buy them at the top) and enjoy the stunning views. It’s free to visit. Be warned there are a lot of stairs, but it’s totally worth the climb! If you’re not up to it you can take a taxi or car to the top as well.

To get there take a “Ponte alle Grazie” bridge (one down from the Ponte Vecchio) across the river into San Niccolo (located on the opposite side of the river from the Duomo) Follow via de San Niccolò to the left to Via S. Miniato through the Porta San Miniato (big stone gate) After you pass through the gates a little way up on your left will be the stairs that lead your to Piazzale Michelangelo. There are signs, so it’s easy to follow + you can usually just follow the crowds!

Grab Dinner at one of Florence’s Many Great Restaurants

Florence has tons of great restaurants, seriously so many that I wrote a full blog post about it. All of the options noted on there are lovely, but grabbing a family style dinner at Il Latini is one of the absolute best ways to experience the food scene in Florence!

Day 3: Tuscany Day Trip from Florence

If you’re a wine drinker, I 100% recommend taking a Tuscan wine tour, but if you’re not into wine taking a day trip to Tuscany is still something I highly recommend. The landscapes are stunning and pictures absolutely do not do them justice.

Tuscan Wine Tour Details:

You can plan your own Tuscan wine tour, but generally this would mean needing to rent a car (the roads are narrow and windy + you’ll be drinking) and you’ll need to research and find wineries on your own. Most of them are small, family run wineries without websites, etc. For this trip I do recommend a guided tour. You’ll learn much more, you don’t need to worry about driving after drinking & the tour guides know the local wineries and in my experience have great recommendations.

The most recent tour I did left Florence in the morning and stopped at two wineries. Both were stunning and the wine was fantastic. You get a tour of both wineries as well as a tasting. These tasting are generous and there is no lack of wine. At the second winery you’ll also have a tradition Tuscan lunch. The food was incredible. We went through Tuscan Wine Tours and I would absolutely recommend them!

Tuscany Options (not wineries)

• San Gimignano is a quintessential Tuscan town. It’s encircled by stone walls built hundreds of years ago. It’s a perfect town for wandering through for a few hours and the views of Tuscany from the edge of the walls is incredible. You can get there from Florence by train & bus, but it was a bit of a pain and I’d probably recommend just taking a bus tour from Florence. I took the train to Poggibonsi and then ended up waiting a long time for the bus to San Gimignano. With all the time spent commuting It probably would have been easier to just take one of the bus tours that stops in San Gimignano, Pisa and Sienna!
• Pisa is close to Florence if you’d like to see the infamous tower! Other than that, there’s not a ton going on in Pisa. Luckily, many of the tours combine a short stop in Pisa with some other classic Tuscan towns, like Siena, Lucca or San Gimignano!
• Siena is famous for it’s signature medieval brick buildings. It’s a great day trip from Florence. There are busses that run between Florence and Siena that
• take about an hour and a half. Siena is also included on many tours from Florence. It’s a small town so you can explore in a couple of hours!

Days 4-5: Rome

The next stop I’d recommend is Rome, the Italian capitol has so many things to see. It’s much larger in scale than Venice or Florence, and you definitely need a few days in Rome itself to even scratch the surface of all there is to see!

Getting There

From Florence (and all other Italian cities) there are high speed trains regularly running to Rome’s main train station, Roma Termini. Rome also has a major international airport, Leonardo da Vinci International Airport, the airport is located about 40 minutes outside of the city. There are regular high speed trains running between the airport and the main train station in Rome. The train runs regularly (every 15 minutes during peak hours) and takes around a half an hour. Follow signs for The Leonardo Express when you’re at the airport.

Where to Stay

As I mentioned, Rome is a massive city with tons of options for where to stay. Certain main tourist sites in Rome are located close together to help you decide where to stay, while others are spread across all areas of the city. I recommend choosing the area where you envision spending the most time and finding a hotel near there.

Area 1:The Colosseum, Roman Forum, Trevi Fountain, Spanish Steps, Pantheon & Piazza Navona all sit on the same side of the river, and these neighborhoods are where I generally prefer to stay. These are not all super close, for example, the Colosseum to the Spanish Steps is about a 30 minute walk, but you can easily navigate between all of the these areas on foot if you choose to stay in one of them. I love the area around the Trevi Fountain and most recently stayed at Relais Fontana di Trevi, located just steps from the fountain with a rooftop bar overlooking the Trevi Fountain. It was a great spot and I highly recommend.

Area 2: The Vatican is across the Tiber River almost an hour walk from the Colosseum (although there is a subway that can get you there) If you plan on spending more time at the Vatican you can opt to stay on this side of the river. I find I spend much more time in the area noted above, so I’ve never stayed near the Vatican, but there a tons of hotel options!

Area 3: Trastevere If you’re looking for a more authentic an Roman experience & to stay somewhere a bit removed from the more touristy areas of Rome. Trastevere has some great options. Just keep in mind you’ll need to travel a bit farther to get to some of the main landmarks!

What to Do in Rome Day 1: Explore Ancient Rome

The Colosseum & Roman Forum are two of the most iconic things to see in Rome and are located next to each other. You’ll need to buy a ticket ahead of time (they do sell out) The ticket will get you into the Roman Forum & Palantine Hill as well. Tickets can be purchased here. If you’re interested in the history and understanding what you’re looing at (particularly in the Roman Forum) I recommend taking a guided tour, which will cover all three areas.

The ancient ruins of the Forum are impressive, but without a guide it’s hard to know what you’re looking at, plus they offer tons of great insight in the Colosseum as well. Tours can be found here (and include the cost of admission) I recommend skipping some of the upgrade options, like adding additional areas of the Colosseum, speaking from personal experience, the main entry tickets get you the best views.

While you’re in the area of the Colosseum, you can check out the Arch of Constantine, which sits right next to the Colosseum, and the Altar of the Fatherland, dedicated to the fist King to unify Italy.

Later at night I recommend:

• Spanish Steps – best place to watch the sunset
• Piazza Navona – great piazza for dinner and drinks
• Trevi Fountain – a must see at night! To get a better view try the Rooftop at the Relais Fontana Di Trevi Hotel

What to Do in Rome Day 2: Explore the Vatican & Trastevere

I recommend exploring the Vatican on a different day than the day you spend in Ancient Rome. It’s a lot to try and see in one day and the two are not close by! The Vatican consists of several things worth seeing, like, St. Peter’s Square, St Peter’s Basilica, The Sistine Chapel (which is a part of the Vatican Museum complex) Entrance to the Basilica is free, but you should beware that the lines will be long almost no matter which time of year you go!

There are many tour options that offer guided tours + skip-the-line access to the Basilica, the Sistine Chapel & the Vatican Museums – I highly recommend this option to save you time and enhance your overall experience! Even if you don’t choose a guided tour, tickets are required for the Sistine Chapel & Vatican Museum, these can be purchased as a combo or individually.

After spending your morning at the Vatican, I recommend exploring the Trastevere, one of Rome’s most famous neighborhoods, that also sits on the same side of the river as the Vatican. There’s not a lot of touristy type destinations to see here, it’s just a great place to experience more authentic Roman culture. I recommend exploring and having dinner over here!

If you check out any of the spots listed on this itinerary or think there is a must see spot in Italy not on this list, please comment and share! To see my other Italy recommendations check out my Italy travel guide here