5 Days in Italy: Classic Itinerary for Rome, Florence & Venice + Itineraries for 4 Alternate Routes

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 several shorter five day itineraries.

My main recommendations for a first timer on 5 day Italy trip would be the Classic itinerary: Venice, Florence (with optional day trip to Tuscany) and Rome. This post covers that itinerary, keep reading below for details on getting around, how long to spend in each place, and more!

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!

Other 5 Day Italy Itineraries to Explore:

🍷5 Days in Tuscany: Vineyards, Vistas & Tuscan Charm

Lose yourself in the magic of Tuscany; fairytale hilltop towns, sprawling wineries, arguably Italy’s best food & wine, + sunsets, sunflowers, Cypress trees & more. This charming region has something for everyone. Find my 5 Days in Tuscany Itinerary here.

🏔️5 Days in the Dolomites: Hiking, Adventure & Mountain Vistas

The Dolomites are absolutely epic for any adventure lover; whether you’re there for hiking, skiing, or luxury hotels with Alpine views – the Dolomites are insanely stunning and a great option for your shorter Italy trip. See my 5 Day Dolomites itinerary here.

🌊5 Days in Puglia: Beaches, Trulli, & Italy’s Oldest City

Puglia is such a hidden gem region of Italy (although it’s becoming rapidly more popular) Puglia boasts charming beach towns like Polignano a Mare & Monopoli, underrated Bari (heaven for foodies) storybook Alberobelow with the unique Trullis & epic Matera (one of my absolute favorite places in Italy) See my Puglia itinerary here.

🍹5 Days on the Amalfi Coast: Sunsets, Coastlines & Postcard Views

The Amalfi Coast is on almost everyone’s bucket list & for good reason. While generally I add the stunning coastal towns of Amalfi at the end of a longer trip to Italy you can also easily spend 5 days exploring the Amalfi Coast alone, don’t miss stunning Positano, lavish Capri, laid back Amalfi, accessible Sorrento & add a stop to the impressive Pompeii archaeological site. Beach clubs, spirtzes, ancient history, & many, many stairs. See my Amalfi Coast Itinerary here.

if you want to fly in and out of one airport this tinerary could be reorganized to day 1 Rome, day 2 Florence, day 3 Florence, day 4 Venice, day 5 Rome. It involves a bit more travel, but depending on the timing of your flights may be more convenient.

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

5 Day Classic Italy Itinerary Map

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!

Venice Day 1 Itinerary

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. Try to get to Venice early and either drop off your bags. Beating the crowds is the best way to go in Venice!

Morning: San Marco

Piazza San Marco & the Basilica di San Marco, which is the main square of Venice. To visit the Basilica & the connected Doge’s Palace I highly recommend booking tickets in advance. They have a variety of options via Viator, including skip the line options that can save you a bunch of time!

Lunch: Rialto Bridge

Grab Lunch near 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! I like Osteria Bancogiro for the canal views and authentic food!

Afternoon: Explore Venice’s Canals

A gondola tour is certainly the quintessential Venice experience, but they are very pricy. There’s a city-wide flat rate so you can’t negotiate, and there’s no benefit to booking in advance. A 30 minute ride is 80 euro during the day and 100 euro after 7PM. A gondola seats 6.

The public Venice ferry system(called vaporettos) is also a cheaper option if you just want to get out on the canals! Line number 1 is the most scenic route if you want to just take a tour through Venice!

Evening: Rooftop Drinks & Dinner

Grab a rooftop sunset drink for some of the best views in Venice at the Top of the Carlton Sky Lounge & Restaurant, and grab dinner along the Grand Canal. I like Cocai Restaurant – amazing views and unreal lasagna!

Day 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 which takes just about 2 hours.

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!

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

Florence Day 2 Itinerary

8AM: Early Train to Florence

I recommend catching an early train so you have the whole day in Florence, but you could opt for a later one. There are tons of trains running al day. This would put you in Florence at 10AM and give you time to drop your luggage at your hotel

11AM 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 insanely 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!

1PM: Lunch at a Classic Florence Spot

Florence has some of my favorite food in the world. For an authentic Firenze experience head to Mercato Centrale (Central Market) for lunch. There are tons of stalls serving local food. Another great option is the wildly popular All’antico Vinaio panini shop (be prepared for a bit of a crazy line!) La Spada is a popular local osteria with AMAZING food if you want more of a sit down option.

3PM: 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

You ticket gets you access to the whole museum (admittedly we didn’t spend too much time here outside of seeing the David, but you can stay as long as you want!)

4PM: Palazzo Vecchio

Palazzo Vecchio is a main square in Florence not far from the Duomo. Palazzo Vecchio is the “Old Palace” and former home of the Medici family. It 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

I also recommend grabbing a drink at one of the cute bars/cafes in this piazza with stunning views of of the palace.

6PM: 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.

You’ll need to head across this bridge towards Oltrarno for your next stop!

7PM: 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!

8PM: 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. In the Oltrarno area (where Piazzale Michelangelo is) here are my favorites:

• Gustapizza – the absolute best pizza in Florence (and maybe anywhere) this place is casual but unreal
• Ristorante Beccafico – love this cozy spot, definitely make reservations!
• 4 Leoni – one of my favorite squares in Florence, this place is such a vibe

Day 3: Tuscany Day Trip from Florence

Tuscnay is one of the most stunning areas of Italy, and I highly recommend taking this day trip. 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, and it’s so accessible from Florence!

If you decide to stay in Florence skip here for my second day in Florence itinerary.

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. This was the one I did most recently, it’s 5 hours so it only takes about half your day, giving you the afternoon & evening to enjoy Florence, but they have tons of options!

Once you’re back in Florence, enjoy a relaxing afternoon discovering some of Florence’s best rooftop bars – my favorites are View on Art or the Rooftop Bar at the Westin

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!

Rooftop Drinks & Dinner

After a long day in Tuscany I recommend a chill afternoon back in Florence. Florence has some stunning rooftop bars. For sunset views head to the Rooftop Bar at the Westin. This place has the very best views, or head to View on Art Rooftop Bar for unreal Duomo views.

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! You definitely need reservations in advance!

Alternative: Spend a Second Full Day in Florence

Uffizi:

The Uffizi is one of the most popular art museums in the world. Spending a second day in Florence gives you time to spend a full morning exploring the Uffizi. Buy tickets at their official website ahead of time. If tickets are sold out through the official website or you’re interested in a guided tour, try Viator

Palazzo Pitti + Boboli Gardens

I definitely recommend a trip to the Boboli Gardens. This is a great place to spend your afternoon.

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

Spend your evening and night with rooftop drinks and dinner (see here)

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. It only takes about an hour and a half to get from Florence

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.

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.

Piazza Navona

I recently stayed at the Navona Queen Rooftop Hotel, this spot near Piazza Navona is one of my favorite areas, and the rooftop had some of the most unreal sunset views ever overlooking St. Peter’s.

Trevi Fountain

I alsolove 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.

Trastevere

 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! This area is also on the same side of the river as The Vatican

Rome Itinerary Day 1: Explore Ancient Rome

Morning: Colosseum & Roman Forum

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 on the official website, if they’re sold out check Viator! 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.

The Colosseum and Roman Forum will take roughly half the day at least.

Afternoon: Pantheon & Spanish Steps

Head to the Patheon (book your tickets ahead of time) The Pantheon is an Ancient Roman temple turned Catholic Church, known for the perfectly circular hole in the roof.

Check out Piazza del Popolo, Villa Medici and then head to the Spanish Steps, this is one of the best places to watch the sunset!

Evening: Dinner & Trevi Fountain at Night

For dinner I recommend heading to the area near the Trevi Fountain/Pantheon Agrodolce, is an awesome spot right near the Trevi Fountain. I highly recommend dinner here!

After dinner head to the Trevi Fountain. It’s always super crowded, but if you want to get some better views try one of the two rooftop bars overlooking the fountain –

• The rooftop at the Hotel Fontana. This small, enclosed bar offers unobstructed views of the fountain (although the glass makes pictures tough, and the general vibe of the Roof Garden at Hotel Relais Fontana Di Trevi is preferable in my opinion, even if the views are more obstructed) It’s 20 euro per person to visit the bar, and it includes one drink, so the price is a bit steep, but it really is one of the best ways to see the entire fountain!
• Roof Garden at Hotel Relais Fontana Di Trevi is one of my favorite rooftop bars in Rome. This small, open air bar is quaint and offers partially obstructed (but still stunning) views of the Trevi Fountain, my favorite monument in Rome. This hotel bar is open to the public, so you don’t have to be a guest of the hotel. Only a few tables have views, but they do a good job letting people move from back tables up to the front if you’re patient!

Rome Itinerary Day 2: Explore the Vatican & Trastevere

Morning: The Vatican

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.

Afternoon: Lunch in Trastevere

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! See all of my favorite Trastevere restaurants here! My top reccs are Tonarello or La Tavernetta 29 da Tony e Andrea

Evening: Sunset at Ponte Umberto I & Piazza Navona

Sunset from Umberto I over the Vatican is absolutely unreal. Piazza Navona – great piazza aperitivo, there are also tons of great restaurants in this area for dinner – see all of my favorite Piazza Navona restaurants here! Il Corallo is unreal

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