5 day Italy itinerary Colosseum aerial view

Epic 5 Day Italy Itinerary (Travel Guide + Restaurants)

This is the most detailed 5 day Italy itinerary you can find. I go on holidays to Italy at least once a year and everything in this travel guide is personally tried. It includes things to see, transportation, hotel & restaurants recommendations + some tips!

Italy is a dream destination for many people. And that’s no surprise! The country has so much to offer – rich history, great weather and amazing food & wine. Combining those is a guarantee for an unforgettable holiday.

It’s impossible to see Italy in a whole year, let alone 5 days. But I did my best in curating this carefully planned 5 day Italy itinerary. It will show you the best of Italy! As a lover of Italian cuisine and history, I go on holiday to Italy at least once every year. And I’ve tried out everything in this itinerary myself to make sure it’s amazing. From the historic sights in Rome to the beautiful Florence, each place I’ve picked will give you a real taste of Italy.

What’s included in my 5 day Italy itinerary

This 5 days in Italy itinerary includes all the information you’ll need for your trip. Starting from hotel recommendations and transportation, through things to see and tips to save time (or money). As a bonus I also included restaurants and cafes that I’ve visited and liked. 

It’s important to note that I made some assumptions when creating this guide to Italy. But if they don’t match your taste or flights, I’ve also added ideas on how you can change and customize it. 

Some of those assumptions are that you’ll be landing in Milan and departing from Rome. If it’s the other way around, just follow the itinerary in reverse order. Another assumption is that you have 5 whole days at your disposal. Last, but not least, this 5 day Italy itinerary is mostly suitable for people visiting each of the cities for the first time. 

Tip: When you have just 5 days in Italy, my advice is to book in advance as many entrance tickets as possible. This will save you a lot of hours waiting in queues. Or in some cases this is the only way to visit a sight as tickets are sold out days or weeks before.

After all, if you decide to spend a bit more time in Italy and explore Tuscany, make sure to check my post about the best luxury resorts in Tuscany. I’ve carefully selected venues ranging from hotels, to resorts with own wineries and luxury villas with a private pool.

5 day Italy itinerary: Day 1 – Milan

The first stop in this 5 days in Italy itinerary is the city of Milan. It’s Italy’s vibrant fashion and design capital and a financial hub. Among tourists it’s famous for its stunning buildings like the Duomo di Milano and the Galleria Vittorio Emanuele II. 

Many people don’t consider Milan as a tourist destination, but I think there’s a lot to see there. Moreover, with its 2 airports, the city is a popular destination for many airlines. That’s especially true for long-distance flights from Asia and North America.

Where to stay in Milan

You’ll be spending 1 night in Milan when following my travel guide to Italy. So my recommendation is to stay in the city center for easy access to shops, restaurants and sightseeing. The area between the city center and the Milan Centrale (the central railway station) is also a good choice. Here are a few hotels that are worth it.

The Square Milano Duomo

The Square Milano Duomo hotel room and bar
The Square Milano Duomo exterior, rooftop restaurant and rooms

It’s located just a few minutes away from the Duomo and all main sites. Plus, there’s a metro station nearby. The rooms are spacious and have all modern amenities like air conditioning, coffee & tea making facilities, safe and more. A nice bonus is that the breakfast is included in the room price, in case you are in a hurry the next day.


Room Mate Giulia

Room Mate Giulia hotel's entrance and room
Room Mate Giulia’s facade and rooms

This trendy hotel is located right at Galleria Vitorio Emanuele and a few steps away from the Duomo and a metro station. The decor is chic and modern and features designer furniture. There’s also a small gym and spa area – something unusual for the Italian city hotels.


Park Hyatt Milano

Park Hyatt Milano hotel view with lobby and room
Park Hyatt Milano hotel view, the lobby and rooms

If you want to stay in one of the most luxurious hotels in Milan, this is your place. The rooms are very spacious and have marble bathrooms. Some rooms even have views of the Galleria Vittorio Emanuele’s interior. The hotel also has a spa, gym and a Michelin-starred restaurant. And the location is right in the city center, steps away from the Duomo.


Itinerary: Day 1 – Milan

Breakfast at GustaMi Bakery (Duomo)

If you want to feel like a local, start your day with a freshly baked croissant and espresso at GustaMi Bakery (Duomo). The bakery offers a wide variety of sweet and salty treats like croissants, focaccias and sandwiches. Its location is also right next to the next stop of this 5 day Italy itinerary.

Duomo di Milano (Milan Cathedral)

The Milan Cathedral, commonly known as the Duomo, is an iconic symbol of Milan. Its construction started in the 14th century and took almost 600 years to complete (finished in 1965)! Crafted from pink-hued Candoglia marble, the facade is a masterpiece of Gothic design and craftsmanship.

You can visit the cathedral itself, but something not to be missed is its terrace. You can either climb the 250 stairs to the top or take a lift. From there you’ll be treated to panoramic views of Milan and the surrounding area. What I liked a lot is that you can see the intricate marble carvings up-close and also take some great photos.

It’s best if you’re at the Duomo at the opening time (usually 9:00). But even then the queue will be long. So it’s best if you buy tickets in advance.

The Duomo (Milan Cathedral) during sunrise
Milan Cathedral square at sunrise – the only time without crowds of people

You can also buy your tickets on site, but you’ll spend a lot of time waiting in line. Note that in order to access the terrace, you need an additional ticket. You can also get an audio guide for an additional cost. Usually you’ll need around 1.5 – 2 hours to see the Duomo and its terrace.

Stroll in Galleria Vittorio Emanuele II

Right next to the Milan Cathedral is one of the most famous and beautiful high-end shopping centers in the world – Galleria Vittorio Emanuele II. It was completed in 1877 and was named after the first king of the Kingdom of Italy. Now it’s one of the oldest shopping malls in the world! It has exquisite decorations including intricate mosaics, frescoes, and statues. 

Nowadays, it’s home to high end fashion stores, restaurants and cafes. It’s quite likely that you’ll see people spinning on their heels in the middle of the galleria. The legend says that if you spin your heel 3 times on the genitals of the bull, this will bring you luck.

Interior of Galleria Vittorio Emanuele in Milan
Interior of Galleria Vittorio Emanuele in Milan

See Leonardo Da Vinci’s Last Supper

One of the must-see attractions in Milan is “The Last Supper” mural painting. It was created by Leonardo da Vinci in the late 15th century. The masterpiece is housed in the refectory of the Convent of Santa Maria delle Grazie.

It depicts the biblical scene of Jesus Christ dining with his apostles for the last time before his crucifixion. It’s famous for its intricate details, realistic portrayal of emotions, and innovative techniques.

In order to preserve the mural, only a limited number of people are allowed per time slot. Also, the time you can spend inside is restricted to 15min. As a result, getting a ticket from the official website is very difficult and you must book at least 3-4 months in advance. Otherwise it’s almost certain that there won’t be any tickets left.

My advice is to book some of the Last Supper guided tours. Usually there’s availability for the same (or next) day visits. And on top of that you’ll learn more about the painting and its history.

What else to see in Milan

The above-mentioned sights are the must-see ones in Milan in this 5 day Italy itinerary. I intentionally left the afternoon without much to do as you may be tired (especially if you are coming from outside Europe). But if you have the energy and want to explore more of Milan, here are a few suggestions on what to do and see.

Sforza Castle

Sforza Castle is a historic fortress with a rich history dating back to the 14th century. Originally built as a defensive structure, it was later renovated and expanded by various rulers, including the powerful Sforza family.

Today, the castle houses several museums and art collections. Exhibits include Michelangelo’s final sculpture, the Pietà Rondanini, as well as collections of ancient art, musical instruments, and Egyptian artifacts. 

You don’t need a ticket to stroll around the castle grounds. But if you want to visit the museum and the art collections, you’ll have to buy a ticket. 

La Scala Theatre

Interior of La Scala theatre Milan
Interior of La Scala theatre in Milan

La Scala is an iconic opera house in Milan, Italy, known for its rich history and spectacular performances. Since 1778, it has been a symbol of Italian opera, hosting premieres of renowned works by composers like Verdi and Puccini. 

With its elegant architecture and lavish interiors, La Scala offers a glimpse into the world of classical music and opera. You can either get tickets from its official website or book a guided tour to learn a lot more about this iconic opera house.

Go Shopping

What’s a visit to Milan without doing some fashion shopping? If you want mainstream shops (H&M, Zara…) head to Corso Buenos Aires. It’s the longest shopping street in the city. But if you are looking for something more luxurious (e.g. Prada, Chanel), then Quadrilatero della Moda (known as Fashion Quadrilateral) is your place. It’s located north-east of the Duomo and Galleria Vittorio Emanuele II.

Finally, if you are searching for high-end stores, then Via Monte Napoleone is the place to be. This prestigious street is lined with upscale boutiques and designer stores, offering the latest in haute couture and exclusive fashion pieces.

Where to eat in Milan

These are a few places where you can eat either for lunch or dinner in this 5 day Italy itinerary. Pasta d’Autore specializes in pasta, but they also have nice pizzas. It’s a cute place for pasta that I think is suitable for lunch. If you want a great charcuterie, then my favorite place is La Prosciutteria Brera.

Must-buy tickets in Milan

When I travel, I buy entry tickets and tours for the most famous sights months in advance. This guarantees me entry, as these places sell out fast! When visiting Milan, these are the tickets you must buy as soon as possible.

5 day Italy itinerary: Day 2 – Florence

On the second day of your Italian trip you’ll be traveling to and exploring Florence. The city is known as the birthplace of the Renaissance and is in the heart of Florence. With its charming streets, historic buildings, and world-class museums, Florence is a must stop.

From Milan to Florence by train

The best (and fastest) way to get from Milan to Florence is by train. The high-speed trains depart from Milano Centrale Railway Station and it takes 2 hours to reach Florence. You can check the train schedule and buy tickets at TrenItalia. Usually there are trains every hour. My advice is to take the one departing at around 8:00 – 9:00AM. In this way you’ll have most of the day to explore the beautiful Florence!

Where to stay in Florence

While staying in Florence during this Italian holiday, it will be best if you book a hotel near the city center. This will give you quick access to all major sights. Less time walking, more time having fun! These are a few nice hotels that I recommend, the first one being my go-to choice.

Hotel Spadai

Hotel Spadai in Florence showing the exterior and room interior
Hotel Spadai with Florence Duomo behind it

This is my favorite hotel in Florence that I’ve been using recently. The 4-star hotel’s location couldn’t be better. The Cathedral is literally 2min away down the street. And Palazzo Vecchio with the main square is 7min walk. The rooms are chic and modern and some even have views of the Cathedral! There’s also a small spa that can be booked and used privately only by you!


Hotel Calimala

Hotel Calimala's rooms, exterior and rooftop terrace
Hotel Calimala rooms feature bare bricks & stones, while the rooftop offers fantastic views of Florence

If you want the best location in the city, then hotel Calimala has that! Palazzo Vecchio is mere 2min away and the famous cathedral is less than 5min walking. Every major thing to see is around the hotel. The rooms have that classic Tuscan feel to them, with marble tiles and brick walls. Yet, still modern and elegant with all the amenities you will need. 

There’s also a rooftop bar and restaurant with gorgeous views of Palazzo Vecchio. That’s also where the breakfast is served! A nice bonus is the small gym.


Itinerary: Day 2 – Florence

Lunch near Piazza della Signoria

What a better way to start your journey in Florence than having a tasty Italian meal! If you want a quick bite, then there are a few options for sandwiches along Via Dei Neri. The most popular one is All’Antico Vinaio, but queues are usually very long. Down the street is La Prosciutteria Firenze which offers equally good sandwiches as well as great charcuterie boards.

For a nice pasta or beef I recommend “L’Osteria”, “Ristorante Braceria Auditore” or “BaccoMatto”.

Florence Cathedral

The Duomo (Florence Cathedral) facade
The Duomo is the most famous landmark in Florence

Undoubtedly the most famous thing to see in Florence is the Duomo (Cathedral of Santa Maria del Fiore) and the Baptistery. The Duomo was structurally completed in 1436 after more than 150 years of construction. Its iconic red-tiled dome, designed by Filippo Brunelleschi, is a masterpiece of Renaissance engineering.

Climbing to the top of the dome offers panoramic views of Florence’s historic center. But considering the limited time you have, my advice is to skip that. If you decide to climb it, know that there are 414 steps to the top and no elevator. You’ll also need a ticket called Brunelleschi Pass that gives you entrance to all monuments of Piazza del Duomo.

If I were you, I would also skip entering the cathedral at all. It’s rather plain (other than Giorgio Vasari’s frescoes of the Last Judgment on the dome) compared to other cathedrals. And you would have to queue for a few hours to get in. The exterior of the Duomo is way more beautiful in my opinion.

Baptistery of Saint John

The Baptistery is the small octagonal structure right in front of the Duomo. It’s one of the oldest buildings in Florence and was constructed between 1059 and 1128. The most interesting thing to pay attention to are the 3 bronze doors. 

The most fascinating one is the East Door (Gates of Paradise) facing the Duomo. It took Ghiberti (the craftsman) 27 years to complete it. He used state of the art back then technique of perspective. Nowadays, the original doors are kept in Museum Opera del Duomo and replica doors are installed on the Baptistery. If you want to enter inside, you’ll need the Brunelleschi Pass.

Accademia Gallery (Galleria dell’Accademia)

Michelangelo's David status in Accademia Gallery
Michelangelo’s David statue in Accademia Gallery

The Accademia Gallery is famous for keeping Michelangelo’s statue of David. It’s one of the most recognisable symbols of Renaissance art. I didn’t know the actual size of the statue before my first trip. When preparing for it, I was amazed to learn that it’s 5.17m / 17 ft tall! Seeing it live was well worth it and it’s one of the highlights in this 5 day Italy itinerary.

Beyond the statue of David, the gallery houses an impressive collection of Renaissance paintings, including works by artists like Botticelli, Ghirlandaio, and Uccello.

It’s a must to buy entry tickets in advance. Otherwise it’s quite likely that you won’t be able to enter the museum. But once you’re inside, you’ll need no more than 30min for your visit.

5 day Italy itinerary: Day 3 – Exploring Florence

On your 3rd day you’ll be exploring the sights along Arno river in Florence. 

Breakfast at the hotel or bakery

You can have breakfast at your hotel. But I love trying the local food whenever I travel and Italy has the best croissants with filling. I like the ones with chocolate or pistachio filling and my favorite ones in Florence were at Vecchio Forno. Another great option, close to the first sight of the day, is bakery Carpe Diem.

Admire the art at Piazza della Signoria

If you haven’t passed through it yet, make sure to check “Piazza della Signoria”. It’s right in the heart of Florence and it’s also where Palazzo Vecchio is. The piazza is full of statues and fountains, including a replica of Michelangelo’s David. Make sure to check “Fontana del Nettuno”, which had major restoration in 2019.

Visit Uffizi Gallery

Uffizi Gallery, Florence, 5 day Italy itinerary
Uffizi Gallery not only has an impressive art collection, but also a stunning interior

The Uffizi Gallery was built in the 16th century by the famous Italian architect Giorgio Vasari for Cosimo I de’ Medici. Originally, it was meant to house government offices (hence the name “Uffizi,” which means “offices” in Italian).

Over time, it became a showcase for the Medici family’s impressive art collection. In 1765, it officially opened as a public museum, making it one of the oldest art museums in the world. Inside you can admire works of art by famous artists like Leonardo, Botticelli, Raffaello, Michelangelo and Caravaggio. You’ll need around 2 hours to see the gallery.

As with any other famous museum, it’s a must to buy your ticket in advance. The tickets have a timed entry, so make sure to be there on time. You can get your Uffizi Gallery Skip the line ticket here.

Lunch in Florence

You can check a few suggestions from Day 2 of this 5 day Italy itinerary. They are right in the area where you’ll be spending the day. And if you don’t like any of them, you may also check “Il Ricettario” or “Ristorante Braceria Auditore“.

Explore the shops at Ponte Vecchio

The bridge is one of the iconic landmarks of Florence. It dates back to the 14th century. What sets it apart from other bridges is the row of shops that line its edges, which sell jewelry, art, and souvenirs.

On top of the bridge is the famous Vasari Corridor, which was a secret passage connecting Palazzo Pitti and Palazzo Vecchio.

Ponte Vecchio shops in Florence
Ponte Vecchio with shops selling jewelry and souvenirs. Vasari Corridor’s windows can be seen on top

Pick your activity

After so much exploring of Florence and Milan in this 5 days in Italy itinerary, you may be tired or want to see something specific. Now is the time to do that! If you have energy and don’t have anything in mind, here are a few suggestions of things you can do.

Visit Palazzo Pitti

Originally built in the 15th century for the Pitti family, it later became the residence of the powerful Medici family. Nowadays the palace showcases an extensive collection of art and artifacts.

There are a few museums and galleries inside the palace, including the Palatine Gallery, the Royal Apartments, and the Gallery of Modern Art. The great thing is that the entry ticket grants you access to all of the museums and galleries. As usual, it’s best to buy your Palazzo Pitti ticket in advance.

Admire the iconic Florence view

We’ve all seen those iconic photos of Florence’s skyline and the Duomo. If you want to see this magnificent view in person, then go to Piazzale Michelangelo. It’s located in the south-eastern part of the city, to the south of Arno river. Going there is not so easy though. It’s a 25min walk from Ponte Vecchio that includes a lot of stairs to climb. And other than the view, there’s nothing else to see in the area. So if you want to go there, my advice is to get a taxi or use public transport.

Learn about science at Museo Galileo 

Museo Galileo in Florence is a fascinating museum dedicated to the history of science, astronomy, and physics. Named after the renowned scientist Galileo Galilei, this museum houses a vast collection of scientific instruments, telescopes, globes, and science artefacts. You can explore interactive exhibits, replicas of Galileo’s experiments, and learn about the contributions of other famous scientists.

Basilica of Santissima Annunziata

The Basilica of Santissima Annunziata in Florence is a stunning example of Renaissance architecture and religious devotion. It was completed in the 15th century and has a stunning interior. I loved the golden ornate ceiling and the intricate details.

The basilica is also home to the miraculous image of the Annunciation, which is said to have appeared miraculously on a wall. The painter was desperate as he couldn’t draw the face of Virgin Mary. He fell asleep and when he woke up, the painting was miraculously completed.

Medici Chapel

Medici Chappel's ornate interior
The Medici Chappel’s ornate interior is breathtaking

The Cappelle Medicee, or Medici Chapels, houses the mausoleum of the Medici family. The interior is stunning, with decorations and statues crafted by Michelangelo and Donatello. If you want to see the final resting place of Lorenzo de’ Medici, book your skip-the-line Medici Chapel ticket now.

Must-buy tickets in advance in Florence

Florence is one of the most popular destinations in Italy (and in Europe). The queues at the museums and sights can be daunting. Quite often you’ll either spend hours queueing or won’t be able to enter at all. So my recommendation is to buy these entrance tickets as soon as possible.

Where to eat in Florence

Some restaurants I would recommend are La Grotta Guelfa, Lo Scudo Ristorante Firenze and Il Vezzo. Another option is to try this amazing Flavors of Florence Tour with Florentine Steak. During that tour you’d be able to try and learn a lot about the typical Florentine meals.

5 day Italy itinerary: Day 4 – Ready, Set, Rome!

It’s time to head to Rome, the eternal city. From ancient ruins to bustling piazzas, there’s always something new to discover around every corner. There’s so much to see and do in Rome. This 5 days in Italy itinerary could easily be 5 days in Rome!

Train to Rome

Pack your bags and head to Firenze Santa Maria Novella train station in Florence. From there, get a train to Roma Termini (Rome’s central train station). The super fast Frecciarossa trains will get you there in ~1h 40min. There are trains every 15-30min. It will be best if you can catch a train at around 8:30AM so that you can be in Rome at 10AM.

Where to stay in Rome 

When staying in Rome during your holiday in Italy, it’s important to pick a hotel close to the city center. In this way you won’t spend a lot of time walking. Moreover, there are a lot of cool restaurants in the area.

U-Visionary Roma Hotel – My favourite hotel in Rome

U-Visionary Hotel in Rome with room interior and rooftop terrace
My room at U-Visionary Hotel and the lovely rooftop terrace

On my last few trips I stayed at U-Visionary Roma Hotel. It has a very central location – just 4min away from Fontana di Trevi, 10min to the Pantheon and 20min walking to the Colosseum. There’s also a metro stop nearby that will take you to the Vatican City. 

The rooms are modern and spacious and the beds are very comfortable. But my favorite thing was the rooftop terrace & bar. You can have your breakfast there and at night it turns into a bar and restaurant. I ended up spending most of my nights there, admiring the city skyline and the views to Monumento a Vittorio Emanuele II.


H10 Palazzo Galla

H10 Palazzo Galla hotel's room and rooftop terrace
H10 Palazzo Galla’s room and rooftop terrace with view of Monumento a Vittorio Emanuele II

Another great option to stay in Rome during this 5 day Italy itinerary is H10 Palazzo Galla. It’s centrally located near Monumento a Vittorio Emanuele II. All the main attractions are 10-15min away walking – like the Pantheon, the Colosseum or the Roman Forum. The rooms are spacious and modern and breakfast is included in the price. This hotel also has a rooftop terrace with great views of the city, where you can have a cocktail at the end of a long day.


Itinerary: Day 4 – Rome

Marvel at the Fontana di Trevi

Once you’ve left your bags at the hotel, it’s time to start the exploration of the last city of this travel guide – Rome! The Fontana di Trevi is a Baroque masterpiece, designed by architect Nicola Salvi in the 18th century. It features sculptures depicting Neptune, the god of the sea, surrounded by tritons and mythical creatures.

Fontana di Trevi in Rome

Legend has it that tossing a coin into the fountain ensures a return visit to Rome. Usually there are a lot of people around the fountain. If it’s hard to get a nice view of it, try going to one of its sides. If you go to the right, on Via della Stamperia, you’ll have a better view as it’s located higher and fewer people go there.

Roman Lunch

The area is full with many trattorias and cafes where you can have lunch. One option not far from our next stop is “Ristorante Trattoria Antonio al Pantheon” for pasta and Roman dishes. If you feel more like having a sandwich or a charcuterie board, head to “Pane e Salame”. For a nice pizza cooked in a traditional brick & stone furnace, go to “Piccolo Buco”.

See the Pantheon

The Pantheon was built over 2,000 years ago by Emperor Hadrian and is one of the best preserved Roman buildings. The Pantheon impresses even before entering, with its massive Corinthian columns. The large bronze doors are among the oldest in the world and the oldest in Rome still in use. They were made 2000 years ago and are so well balanced that despite their enormous weight, a single person can easily open them.

Pantheon's interior and exterior, Rome
The Pantheon’s interior is even more stunning than its exterior

Once inside, you’ll be fascinated by the massive dome with an oculus at its center. Dome’s diameter is 43m (142 ft) and it’s the largest unreinforced concrete dome in the world! What’s also large are the queues to enter.

Unless you want to spend over an hour waiting, it’s best to buy a Pantheon Fast-Track Ticket in advance! That’s what I did and entered without queueing.

Pass by Monumento a Vittorio Emanuele II

From the Pantheon walk to Monumento a Vittorio Emanuele II. It’s a grandeur neoclassical monument built in honor of Victor Emmanuel II, the first king of a unified Italy. You won’t be entering inside, so keep walking to the right of the monument on Via del Teatro Marcello.

Optional: ​​Basilica di Santa Maria in Ara coeli

Right behind Monumento a Vittorio Emanuele II there are 2 stairways going up. The first one with the many stairs will take you to Basilica di Santa Maria in Ara coeli. It was built in the 12th century and has an impressive ceiling and frescoes painted by Pinturicchio.

Campidoglio square

If you take the second stairway you’ll reach Campidoglio square. It was designed by Michelangelo and is surrounded by several museums. Unfortunately, you won’t have time to enter any of them. But it’s a lovely piazza and is along the way to the next stop in this 5 day Italy itinerary!

View of the Roman Forum

5 day Italy itinerary Roman Forum
View over the Roman Forum’s remain from Via del Campidoglio street

What’s a trip to Rome without a visit (well, sort of a visit) of the Roman Forum! It’s a large excavated area of the heart of ancient Rome. There you can see the remains of many government buildings, temples and squares. Many important events in daily life in ancient Rome happened at the Forum. Be it public announcements, processions, public speeches or criminal trials.

It would take you a few hours to see the Roman Forum, but there’s not enough time for that. What you’ll do instead is, in my opinion, even better – have a view of the Forum from above! When you are at Campidoglio, take the street on the right of the central building (Via del Campidoglio). After a few steps you would see a spectacular view of the Roman Forum!

See the Colosseum

Well, you are not going to fight there, just see the Colosseum, so worry not! Now head back to Campidoglio square and take the street on the left of the central building. You would pass along a terrace offering more views of the Roman Forum. Once you reach Via dei Fori Imperiali turn right and walk until you reach the highlight of this 5 day Italy itinerary – the Colosseum!

The Colosseum is a massive amphitheater, commissioned by Emperor Vespasian in AD 72. It was a center of entertainment, hosting gladiator fights, animal hunts, and dramatic performances for over four centuries. In its prime time, it had a capacity of 50 000 spectators! Today you can explore the vast network of tunnels and corridors and also visit the arena itself. Over 4 million people visit the Colosseum each year!

Colosseum exterior and arena's remains
Colosseum in Rome. Best photo spot with fewer tourists is at L.go Gaetana Agnesi square, near the metro station

Even though the Colosseum is the top sight of this Italy guide, you won’t have time to enter inside. A few months ago during my last visit I spoke with someone who waited a few hours to buy their ticket. Then you have another queue to enter the Colosseum as there are security checks. If you insist on visiting it, your best choice is to buy tickets in advance or get a private tour.

Visiting the Colosseum
Timed entry ticket: Colosseum, Roman Forum & Palatine Hill – combined ticket for the 3 sights
Best quick tour: Colosseum Tour with Access to the Gladiator Arena – a 1.5 hours tour, skipping the entrance queue and going directly to the arena. All that accompanied by experienced guide to tell you all you need to know about the Colosseum

Customizations of day 4 of 5 day Italy itinerary

The Colosseum is something a lot of people want to visit. If this is your case and you’re not sure you’d have the time or energy to do so at the end of the day, do the following! My advice is to follow the itinerary for day 4 in reverse order. So start with the Colosseum and finish with Fontana di Trevi. In this way you’ll have more energy and time for the must-see attraction (the Colosseum in your case). After the Colosseum you may skip some of the remaining sights if you don’t have time for them.

Another thing you can do is to skip the views of the Roman Forum, the Campidoglio square and Monumento a Vittorio Emanuele II. And instead fill the time either with a visit to the Roman Forum and Palatine Hill or just stroll along the small streets of Rome. If you haven’t walked through Piazza Navona yet, that’s a chance to enjoy a cocktail there.

5 day Italy itinerary: Day 5 – Vatican City

The main focus of the last day of this guide is not Italy, but a small city-state inside Rome – Vatican City! Home to the Pope and the administrative center of the Roman Catholic Church, Vatican City is a pilgrimage site for millions of faithful believers each year. It’s also home to many artifacts, art and precious objects.

How to visit Vatican City

As part of this 5 day Italy itinerary you’ll be visiting the 2 most popular sights in the Vatican City – the Vatican Museums and St. Peter’s Basilica. They are one of the most popular tourist sites in Italy. Therefore, the queues are very long and it takes hours to enter. What’s even worse is that there’s one queue for the Vatican Museums and then another one for St. Peter’s Basilica.

Vatican city and view over Rome
The view from the top of St. Peter’s Basilica is marvellous

There are 2 main ways to visit the attractions. First one is self-organizing it and waiting in both queues. The second one is to book a guided tour. It’s the more expensive option, but it will save you hours of your time.

Best way to see the Vatican Museums and St. Peter’s Basilica is through this guided tour.
Benefits: Can be booked just a few days before your visit. But more importantly – you’ll skip all the queues and enter both sites without waiting. Plus, a tour guide will tell you all you need to know about the things you see.

Self-organizing your visit is a bit more difficult, but not impossible. The first time I visited the Vatican City was by doing it all myself. First of all, it’s a must to book your entry ticket to the Vatican Museums at least 1-2 months in advance. During the summer period tickets are often sold out and there are no available slots for any date. Thus, you should plan your visit a few months in advance. When there are tickets available, I would buy tickets for around 10:30-11:00 AM.

On the day of my visit, I would first go to the St. Peter’s Basilica. There are no skip the line options here, so it’s best to be there early in the morning. The Basilica opens at 7:30 and even then there’s a long queue. Thus, my advice is to be there as early as possible. You’ll go through an airport-style security check and then enter the Basilica itself.

Once you are ready with the Basilica, you can visit the Vatican Museums. Just make sure not to miss your time slot and also leave some time in case there are other people waiting on the skip-the-line queue. It’s important to note that there’s a 1km (0.6mi) walk from the Basilica to the museums’ entrance!

If you decide to first visit the museums and then the basilica, you should know about this tip! When you are exiting the Sistine Chapel, instead of taking the exit at the near left corner, take the one on the far right corner. It will take you to St. Peter’s Basilica in the area right after the queues. But this shortcut is not always open or might be open only for organized tours. If you decide to take the risk and use this shortcut, I would book a ticket for around 8:00-9:00 AM.

The Vatican Museums

Vatican museums, 5 days in Italy
The Vatican Museums are a must visit when in Rome. Even the exit (the Bramante staircase) is spectacular.

Vatican Museums are a home to one of the world’s most extensive collections of art and artifacts. Some of the more famous things to see are the School of Athens. It’s a fresco in a room called “Stanze di Raffaello” in the Apostolic Palace in the museum, painted by Raphael. Another thing not to miss are the ancient Roman sculptures at the “Belvedere Courtyard”. The most popular thing in the Vatican Museums is undoubtedly the Sistine Chapel and its ceiling painted by Michelangelo.

The entrance and exit of the museum is located on Viale Vaticano street, on the northern side of the Vatican City. The queue goes besides the tall walls of the city. The opening times are 8AM – 7PM (last entry is 5PM) and the entrance is free every last Sunday of the month. My advice is not to visit it that Sunday, as queues are even longer. You can also check the map of the museums to see the locations of the rooms you don’t want to miss!

Book your Skip the line Vatican Museums entry ticket as soon as possible (at least 1-2 months in advance)! This will guarantee you entrance and save hours waiting.

St. Peter’s Basilica

Interior and exterior of St. Peter's Basilica
St. Peter’s Basilica is the largest church in the world!

The basilica is one of the most iconic landmarks in Vatican City. It’s also the largest church in the world! The interior is stunning and the place feels so big – I wasn’t prepared for this grandeur. One of the most iconic things to see inside is Michelangelo’s Pietà statue. It portrays Mary holding the dead body of Jesus after the crucifixion. 

Another thing not to be missed is Bernini’s Baldacchino. It’s a large Baroque sculpted bronze canopy over the high altar of the basilica. You can also climb the dome and admire the stunning views over Rome. The basilica is free, but you’d have to pay to climb the dome. There’s an elevator to the roof and after that you have to climb 320 steps to the top. But the view is totally worth it!

Lunch near Vatican city

It’s a touristy area, but there are a few nice places for lunch after visiting the Vatican City. For pasta or salad, go to Borghiciana Pastificio Artigianale. For Roman style pizza (it’s rectangular with thicker dough) you should go to La Locanda di Pietro. And if you prefer something quick, go to Pastasciutta.

Walk by Castel Sant’Angelo

Castel Sant'Angelo and bridge with angels

Castel Sant’Angelo is a small fortress in the heart of the city. Originally it was commissioned by the Roman Emperor Hadrian as a mausoleum for himself and his family. Later the structure served as a papal residence, prison and military fortress. It’s connected with the Vatican city via the Passetto di Borgo. A 800m (0.5 mi) long corridor used by the popes as an escape route.

Nowadays, the fortress is a museum that you can visit. Though I think that you will be too tired to look at yet another museum at the end of this 5 day Italy itinerary. I wasn’t that impressed by the interior. But if you want to visit it, it’s best to book this Castel Sant’Angelo Skip-the-Line Entry ticket for a quick, hassle-free entrance.

Climb the Spanish Steps

The Spanish Steps is a popular gathering spot for locals and tourists. This grand staircase, consisting of 135 steps, connects the Piazza di Spagna at the base with the Trinità dei Monti church at the top. They are very beautiful in the spring when the vibrant azalea flowers bloom. But after all, these are just a lot of steps with a church at the top and a fountain and their base. So don’t expect much out of them.

Spanish Steps in Rome with Trinita dei Monti at the top

Must-buy tickets in advance in Rome

Rome is one of the most visited cities in the world! Therefore, if you want to get the most out of this 5 days in Italy itinerary, you must prepare beforehand. Tickets for many of the attractions usually sell out weeks in advance.

My advice is to buy the following tickets as soon as possible
Colosseum Tour with Access to the Gladiator Arena – optional, if you want to visit the Colosseum
Vatican Museums – entry ticket to the museums for a specific time slot. Must be bought at least 1-2 months in advance!
Castel Sant’Angelo skip the line ticket – optional, in case you decide to visit the castle

Where to eat in Rome

Pasta at al42 and carbonara at La Fraschetta di Castel Sant’Angelo
al42 (left) and carbonara at La Fraschetta di Castel Sant’Angelo (right)

One of the best pasta Carbonara I’ve had was at “La Fraschetta di Castel Sant’Angelo”. I definitely recommend it! Another great pasta place is “al42 by Pasta Chef rione Monti” near the Colosseum. It’s more suitable for a quick bite and there’s a long queue even before their opening time. But the pasta was so good that I changed my plans on the day of my flight to be able to eat there again. I almost missed my flight, but it was well worth it!

If you look for a place closer to the Spanish Steps, then go to “Colline Emiliane”. They prepare their pasta fresh every morning. Last, if you look for a restaurant in the city center, “Ristorante Trattoria Antonio al Pantheon” is your place.

When it comes to gelato, go to “Gelateria La Romana” or “Gelateria Artigianale Il Capriccio di Carla Roma Monti”. Many people queue at some of Venchi’s locations, but the gelato there is not that good. It looks good for social media photos, but the taste is not great. And if you fancy a quick tiramisu, the best one is at “Two Sizes“! Many influencers recommend “Pompi“, but their tiramisu was awful and I didn’t even finish it.

Gelato from La Romana and tiramisu from Two Sizes
Gelato from La Romana (left) and tiramisu from Two Sizes (right)

If you want to just enjoy the food and not think about making reservations and select restaurants, then go on a food tour! Local guides will take you to several restaurants where you’ll sample different Italian foods and wine. I recommend these tours:

Roman Street Food on a Guided Small Group Tour – try 5 different street foods + wine and beer. All this combined with a tour of Trastevere or the Jewish Quarter. 
Guided Food Tour in Trastevere – taste at least 10 different roman foods. From cured meats and aged cheese, to pasta and gelato. All this paired with wine from the Lazio region

Customizations of 5 day Italy itinerary

It’s impossible to create a universal 5 days in Italy itinerary that will satisfy everyone’s taste and desires. I selected the most iconic cities and sights. But if you’ve already been to some of those or want to see something in particular, you can switch a sight or a city with the one you like more. Here are some ideas of things you can do.

Venice is a dream destination for many. It’s a very beautiful and romantic city. If your flight lands in Milan in the morning, you can go from the Airport to Milan’s central railway station. From there, you can get a direct train to Venice. The journey is around 2h 30min. Then spend the first day in the city and on the second day take a train to Florence, following my itinerary from there.

When selecting a hotel in Venice, pick one either close to the train station or near the public transport boat stops along the main canal. The city has narrow cobblestone streets and a lot of bridges. There are no cars in the city and moving around with a big heavy suitcase is challenging. 

Another possible change of the 5 days in Italy itinerary would be to take a train from Milan to Florence on the day you land in Milan. The direct train takes a bit less than 2 hours to reach Florence. In this way you’ll have 1 more day in Florence. So you can do a day trip to Bologna or Pisa, or book a tour like this Chianti Wineries Tour with Food and Wine Tasting.

Best time to visit Italy

The best time to visit Italy is usually in spring (April to June) and fall (September and October). During the summer the weather is unbearably hot and there are way too many tourists. During spring, the weather is nice and not too hot, and you can see beautiful flowers everywhere. In the fall, it’s still warm and you can see the leaves changing color. There are fewer (albeit still a lot) tourists during those seasons. 

My personal preference is to visit Italy in May or the end of September/beginning of October. If you are going to the southern parts of the country (e.g. Sicily), I would go at the end of April or October. Finally, if the purpose of your trip is relaxing by the sea and on the beach, then embrace the summer months!

FAQs about 5 day Italy itinerary

Can you do Italy in 5 days?

Yes, you can visit Italy in 5 days, but you’ll see only the most famous sites. To get the most out of your time, you’ll have to plan everything in advance. My post will help you with that! It includes detailed itinerary with things to see, first-hand restaurant & hotel recommendations, tickets to buy in advance + some tips.

How many days in Italy is enough?

It depends a lot on your interests, but 2 weeks should be enough to see a lot of Italy. You’ll be able to explore Venice, Tuscany (Florence, Bologna and a bit of the countryside or Pisa), Rome and Naples. You can swap some cities with things you are more interested in – be it Amalfi coast, Cinque Terre or Sicily.

When is the best time to go to Italy?

The best time to go to Italy is either the spring months of April to June or in the autumn (September and October). The weather is nice and warm, without being too hot. There are also less tourists compared to the summer.

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Things to see + hotels & restaurants I tried for 5 days in Italy itinerary


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