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Updated June 2026

When traveling in Italy, one of my tour guides shared a family joke with our tour group: “Mama, basta la pasta!”, which translates to “Mama, stop the pasta!” I could easily see how this phrase would come to be—Italians love their pasta and every restaurant serves it in many forms. I wasn’t complaining though and couldn’t get enough pasta during my short nine days traveling from Milan to Florence to Rome.

Besides the incredible cuisine, Italy has a lot to offer any type of traveler, from couples looking for romance, to history buffs, to outdoor enthusiasts. Read on for my detailed itinerary involving some of the best places to visit in Italy.

Quick Tips for Visiting Italy

Train travel is the most efficient way to get around the top places to visit in Italy, along with public transportation within each city. I used Trenitalia to get from Milan to Florence, Florence to La Spezia (near Cinque Terre), and Florence to Rome.
If you are short on time or public transportation isn’t available, there are taxis in many major tourist locations, as well as Uber. You should be able to find rides in Milan, Florence, and Rome.
My trip started north in Milan and ended in Rome. I flew into Milan (MXP) and out of Rome (FCO). Check Expedia for the best deals on international flights, including multi-city trips.
If you have to do any walking around the city with your luggage, just keep in mind that many streets are cobblestone and bumpy. Pack light to make the walk a bit easier.

Looking for a romantic Italian trip itinerary? Keep an eye out for my North Italy itinerary, coming soon!

An Itinerary of the Best Places to Visit in Italy

Day 1 - Milan Highlights: The Duomo & High End Shopping

I started my Italy adventure in one of the northernmost cities, Milan, flying into the international airport from Paris. Milan is the largest metropolitan area in Italy, known for its fashion and business. I only spent a day there, visiting sites around the Piazza del Duomo.

I purchased tickets in advance to visit the inside and rooftop of the Milan Duomo, easily one of the most incredible cathedrals I’ve seen. The view from the top was stunning, as were the statues and spires I climbed among. The inside of the cathedral is also amazing and well worth the visit. I wasn’t able to get tickets in time, but if you book this Milan Duomo tour, you can also visit Da Vinci’s Last Supper painting.

Part of the Piazza del Duomo borders the Galleria Vittorio Emanuele II, which is the birthplace of high end brands, such as Gucci, Versace, and Prada. It was fun to window shop, people watch, and enjoy the atmosphere inside the gorgeous open building. I also had my first amazing Italian pizza there at a local chain called Spontini—the slices are huge and everything about it was perfect!

Don’t want to miss any Milan highlights? Take a guided walking tour that includes the Galleria and other fantastic sights.

Where to stay in Milan: Mazzini Suites, near Milan’s city center

Day 2 - Florence Architecture & City Walking

After Milan, I traveled by train two and a half hours south to Florence. Florence is much smaller than Milan, but is still bustling and full of interesting people and things to do. I fell in love immediately with the architecture, art, and the dozens of piazzas dotting the city!

On my first day there I visited the Cathedral di Santa Maria del Fiore, which is the icon of Florence. Its red dome and the Giotto Tower stand out in the landscape of the city. There was a loooong line to enter the cathedral, but it was worth it to see the dome from below and wonder at the perfect exactness of its many layers.

I then visited another building, the Basilica di Santa Croce, where Galileo and Michelangelo are buried. It was neat to walk around the inside and gaze upon statues and tombstones of people, both well known and long forgotten.

The second part of the day involved walking along the Arno River to the Ponte Vecchio bridge, lined with beautiful jewelry shops, and ate delicious arancini and other Italian foods at the San Lorenzo Market.

Gelato of the day: I ate gelato from GROM and started a habit of having it every day in Italy with no regrets!

Where to stay in Florence: Atelier delle Grazie, near Florence’s city center

Day 3 - An Unforgettable Tuscan Tour

To get the most out of visiting Tuscany without a car, I booked a tour through Get Your Guide and was able to see Pisa, Siena, and San Gimignano, as well as beautiful orchards and vineyards throughout the countryside. The day was full of breathtaking sights and delicious food.

The tour started in Siena, the home of the Palio horse racing competitions. I took first year Italian in college and my instructor, who lived in Italy for two years, said this was his all time favorite city, so I had high expectations. Siena is beautiful, with large stone walls that border the city and cobbled streets, but it didn’t impress me quite as much as Florence. However, I loved the unique look of the emerald and cream striped tower of the Siena Duomo (entry not included in the tour) and learning about the Palio races in the Piazza del Campo.

The next stop was lunch at an incredible restaurant in the countryside, right in the heart of Tuscany! They served meats and bread for an appetizer and then presented the most delicious pasta I’ve ever had! I can’t even explain why it was so tasty—maybe it was the setting and the views of the rolling green hills that added to the experience.

After lunch I discovered my favorite small town ever—San Gimignano (Queenstown in New Zealand is a close second). I had never heard of this town before visiting it, but I am so glad I did!

Cobbled narrow streets, sandy-colored towering medieval walls, and a small town square with a well in the center created the charm of this beautiful tiny city. I walked through the main pedestrian-only road and then past the curves and up a hill to amazing sights of Tuscany. I finished my lovely time there eating gelato and visiting adorable lemon, lavender, and ceramic shops.

After a long drive to Pisa full of cheesy tour guide jokes, we arrived at the most famous part of the tour. We only had an hour in Pisa and spent it walking through crowds of knock-off souvenir sellers, taking cliché pictures pretending to hold up the leaning tower of Pisa, and people watching. The tour guide warned us to watch out for scammers and pickpocketers, but luckily all I saw was a guy in a Subway sandwich costume.

Pisa was fun, not my favorite part of the tour, but definitely a place I’m glad I can say I’ve been. Overall, it was a really great and exciting day that I would love to live all over again! Book your own tour of Tuscany here.

Gelato of the day: World champion gelateria called Dondoli in San Gimignano

Day 4 - World-Famous Florence Art

While in Florence, it would be crazy not to visit an art galleries, just how it’s unheard of to skip Hobbiton in New Zealand if you’re a fan of Lord of the Rings!

I’m not the most avid art connoisseur, but I loved seeing Renaissance art, created by the masters themselves, in person. I started my day at Boboli Gardens, a famous sculpture and botanic garden established by the Medici family. It showcases Renaissance statues amidst beautiful hedges and fountains. I loved walking through the perfectly manicured forest.

I spent much of the rest of the day at Uffizi Gallery—famous for housing hundreds of art pieces by famous Middle Age through Renaissance era artists, including Giotto, Botticelli, Leonardo, Raphael, Michelangelo, and Caravaggio. My favorite collection was Botticelli’s, which included the Birth of Venus and Primavera.

Book on Get Your Guide to be able to visit both Boboli Gardens and Uffizi Gallery with one ticket.

The highlight of my day exploring art was visiting the Galleria dell’Accademia, which contains Michelangelo’s David. This was definitely one of my favorite art piece and it was larger than life—so detailed with views from every angle. Even if you don’t know much about art, you can still appreciate the skill it took to create such a masterpiece!

I ended my day at Piazzale Michelangelo, set on a steep hill that provides incredible views over the city. It was so romantic and enchanting.

Gelato of the day: Venchi, which, in my opinion, is the Gucci of gelato shops. They had a chocolate fountain wall, fancy chocolates for sale, and smooth, creamy gelato!

Day 5 - The Colorful Coast of Cinque Terre

When I see pictures of Cinque Terre—which are everywhere because it is SO photogenic and one of the best things to do in Italy—I don’t just think of colorful buildings carefully perched above a turquoise ocean. I see memories of a cat curled up on a parked boat in the sun; rocks I sat upon, watching the waves crash back and forth along the shore; a young couple playing with their unleashed dog on the tiny Vernazza beach; fresh lemon gelato; terraces lined with lemon trees; and a secret rocky shore with a cave-like entrance.

Taking the local train between the five small towns was one of the most picturesque days of my life! I visited Manarola, where the famous colorful pictures come from, Vernazza, which has a small beach and a relaxed atmosphere, and Monterosso al Mare, which is the biggest town with the largest beach and incredible views into the ocean.

When I visit Italy again someday, I’ll be sure to stop at all five towns, spend at least a night in the area, and do some hiking!

Gelato of the day: Fresh lemon gelato in Manarola

Day 6 - The Historic Side of Rome

After traveling even further south, three hours by train from Florence, I arrived in Rome. I was eager to hit the ground running after dropping off my luggage in the cute Trastevere region of Rome. I first made my way to Capitoline Hill, which overlooks the Roman Forum and Colosseum.

I planned to visit Capitoline Museum, but arrived during their break and decided not to wait around for it to open again. It was okay though—after a week in Paris and another in Italy I was all museum-ed out! Instead, I spent my time walking around enjoying views of the Roman Forum. I also visited the Mamertine Prison where biblical figures, Peter and Paul, were imprisoned.

My ticketed time to enter the Colosseum was getting near, so I made my way to the giant amphitheater. I was appalled at the hordes of aggressive salespeople trying to sell overpriced tickets, souvenirs, and water bottles! It got really annoying, so I ended up waiting in line early just to avoid the people.

Once I entered, the experience got better, but there was a lot of construction inside, which made it hard to imagine what it was like during ancient times. I did enjoy walking around the perimeter of the amphitheater, reading about the history and shopping for cool souvenirs.

After my visit, I made my way to the nearby Roman Forum, which was included in my ticket. It was a neat area, full of Roman ruins and ancient buildings.

I then toured San Clemente Basilica, which is a Catholic church above an ancient Pagan temple! I went underground and found remains of Pagan worship, as well as early Christian worship. It was a really unique experience and the best part is that it was uncrowded, unlike much of the rest of my day.

For dinner, I dined outside at a restaurant in Trastevere, which served chicken cacciatore that blew me away! Italian cooking can’t be beat.

Where to stay in Rome: Dimora Cardinal Moroni, in Rome’s romantic Trastevere neighborhood

Day 7 - Touring the Amalfi Coast & Pompeii

Bright and early the next morning I headed to the last tour of my trip, booked through Walks of Italy. We drove for what felt like forever along beautiful Italian roads until we reached the Amalfi Coast. The bus stopped on the side of the road so we could try freshly squeezed orange juice and lemonade—the best I’ve had ever had! We then drove along cliffs and perilous sharp turns in the road to Positano.

Positano is everything I think of when I imagine days of basking in the warm Italian sun. It has the ocean views, the white cliffs, the lively, walkable city streets, and the crowded beach! I loved spending time wandering around the town and taking in the sights and smells. On the bus to Pompeii, the tour guide read a beautiful account from John Steinbeck about why he loved Positano and much of it rang true to my experience.

Pompeii was another kind of amazing. This highlight of my trip led me on a guided tour through a town destroyed and subsequently preserved by the volcano, Mt. Vesuvius. I saw the ash-covered mummified bodies of victims that died in 79 A.D. and were still posed in protective stances. I then walked through the ruins of the town, much of which is still buried under feet of ashes and yet to be uncovered.

Without a guide, this tour probably would not have been as exciting and I would have missed out on the hidden treasures I discovered. However, with a tour guide I learned so many intriguing facts—I saw where the Pompeian’s communal kitchens were with huge pots, visited baths and an ancient mansion, saw the town square, and even learned about the grooves in the road. It was fascinating!

Day 8 - Relaxation in Rome

The next morning in Rome, I took a bus to the far east side of town to visit a modern religious site—the temple for the Church of Jesus Christ of Latter-day Saints. This structure was gorgeous, with oval walls and tall spires. I didn’t go inside the temple, but I did go to the visitor center, which had statues of Jesus and his twelve apostles, as well as a beautiful stained glass installation with intricate detail.

I made my way back to the center of Rome and went inside the Basilica di San Pietro in Vincoli. It was a short trip to visit Michelangelo’s Moses statue, which was really cool, and to see the chains that Peter allegedly wore while in prison. My favorite moment while in that part of town was walking through a cobbled tunnel where a humble man was playing classic Italian songs on his accordion.

One place many people pass by in Rome, but don’t visit, is the Pyramid of Cestius, built in the first century B.C. The pyramid was used as a tomb and is now surrounded by a cemetery, including tombs of famous people, such as John Keates and Percy Bysshe Shelley. My favorite thing about it was the cats that were roaming around!

My last stop for the day was Aventine Keyhole. I got in line to look through a keyhole that provides a unique view of St. Peter’s Basilica just as it started pouring rain! By the time I got to the keyhole (completely drenched), I could only see a grey view of thick clouds. Good thing it was free.

For dinner, I went to a tiny shop called Trappizzino. This delicious little restaurant specializes in trappizini, which are basically fluffy bread cones filled with yummy-ness. I was obsessed with the chicken cacciatore one and also enjoyed the meatball one. In fact, I loved it so much I ended up eating there the next day, too!

Day 9 - The Vatican City Highlights

I began my last day in Italy with a trip to Vatican City. My first stop was to the Vatican Museums, and thank goodness I got skip-the-line tickets because the line was already ginormous, wrapping around the walls of the whole area!

The museum was a maze, filled with artifacts from all over the world, from mummies to animal sculptures to crowns. The highlight of the area is definitely the Sistine Chapel, containing The Last Judgement by Michelangelo. The room was magnificent and covered in religious paintings. It was like reading a Where’s Waldo book—only it’s more like Where’s Jesus. Leading up to the room was my actual favorite part—the hall of maps! It depicted huge maps of Italy through the ages and I’m a geography nerd, so it was awesome to be surrounded by them.

St. Peter’s Basilica is another must see in the Vatican, and it had a huge line to enter, so luckily the Vatican Museums entry included skip-the-line tickets for this as well. The basilica was grand and awe-inspiring. Bernini’s giant canopy structure was the highlight, as well as the Pieta, a sculpture by Michelangelo depicting Mary holding Jesus after his crucifixion.

My last adventures in Rome led me through some major piazzas, including Navona, where the magnificent Fountain of Four Rivers is located. I preferred this fountain over the next one I visited: Trevi Fountain. Yes, the Trevi is such an icon of Rome and pretty cool to see in person, but I found it to be way too crowded for such a small area. However, that didn’t stop me from still throwing a penny in it in hopes of returning to Rome someday!

My last sight to see in Rome and all of Italy was the Pantheon. I would say I saved one of the best things for last! The dome ceiling of the ancient Roman structure was massive and I loved having 360 degree views of the room. Floor to ceiling was masterfully planned out in this altar to all gods.

There are so many incredible places to visit in Italy and this itinerary covers some of the very best. If you are visiting for the first time, feel free to copy this itinerary and enjoy all the sights, sounds, and tastes the beautiful country has to offer!

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