Italy has long been the dream destination for travelers who crave history, culture, food, and breathtaking landscapes. With its charming cities, art-filled streets, and stunning coastlines, it’s easy to see why Italy remains a top choice for international travelers (there’s a reason it’s the 5^th most visited country in the world by tourists). If you’re planning to visit Italy and want to make the most of your two-week vacation, this itinerary will take you on an unforgettable journey through five of the country’s most iconic destinations: Naples, Rome, Florence, Venice, and Milan.

Now this itinerary covers almost exactly what I did on my first solo trip abroad back in 2019 and takes you through some of the most famous spots of Italy. It gives you a great overview of the country, but it by no means shows you everything there is to see in Italy. Italy is such a fantastic place where I feel as though you could go back to numerous times and still discover something new. If you have more time to spend there than I did you should check out these other destinations within Italy, or feel free to swap them for anything in this itinerary if it fits your style. I’d recommend checking out Cinque Terre, Lake Como, Turin, Sicily and Sardinia if you want to see even more of what this beautiful country has to offer. 

Here is a quick overview of the itinerary:

• Days 1-4: Naples
• Days 4-7: Rome
• Days 7-10: Florence
• Days 10-12: Venice
• Days 12-14: Milan

With that said, let us begin our 2-week itinerary in the beautiful country of Italy. 

Days 1-4: Naples – The Heart of Southern Italy

Your Italian adventure begins in Naples, a vibrant city that serves as the gateway to some of the country’s most famous historical and natural sites. While it may not always get the same attention as Rome or Florence, Naples has an undeniable charm that captivates visitors. From its bustling streets to its proximity to Pompeii and the Amalfi Coast, Naples offers a perfect mix of authentic Italian culture, history, and cuisine. People often associate Naples with the mafia and everywhere I look online people always mention that Naples is less safe than the other places on this list, but I did not experience this. That’s not to say that you shouldn’t be smart and always be aware of your surroundings, but if you use common sense as you should anywhere you travel, then you will love this city. 

I am not sure if it was just because Naples was my first Italian city I had ever been to and the adrenaline of solo travel was still fresh, but Naples was by far my favourite city on this list. Yes, it’s a little grungy, but the food and the hospitality here are unmatched by any other Italian city that I visited.

Day 1: Arrival and Explore Naples

Arriving in Naples, take the afternoon to stroll through its lively streets, experiencing the juxtaposition of chaotic energy and ancient beauty. Start with a visit to Piazza del Plebiscito, the city’s grand central square, surrounded by landmarks like Royal Palace of Naples and San Francesco di Paola Church.

From there, wander through the Spaccanapoli, the narrow and bustling street that cuts through the heart of the historic center. This area is brimming with churches, local shops, and pizzerias—don’t miss trying a slice of authentic Neapolitan pizza at one of the many pizzerias, like Sorbillo.

Day 2: Pompeii and Mount Vesuvius

Take a day trip to the world-renowned ruins of Pompeii, the ancient city frozen in time after the eruption of Mount Vesuvius in 79 AD. 

Pompeii is easily accessible by train and only takes about an hour to get there. Spend a few hours exploring the remarkably well-preserved remains of homes, streets, and public buildings, and learn about life during the Roman Empire. I booked a small group tour through Air bnb with a local guide who was studying to get her PhD in history. I highly recommend prebooking a tour guide as they can thoroughly explain what you are looking at and help to bring the magic of Pompeii to life. There are plenty of tour guides that wait out front of the entrance to Pompeii, but they are often much busier and much more expensive than some of the prebooked ones. After Pompeii, take a hike up to Mount Vesuvius for sweeping views of the Bay of Naples or if you’re still on a quest for more history, head towards Herculaneum to see even more well preserved ruins but with less tourist crowds and better-preserved frescos. 

Day 3: Amalfi Coast and Sorrento

Dedicate this day to one of Italy’s most stunning coastal areas, the Amalfi Coast. You can either rent a car or take a local bus to visit picturesque towns like Positano, Amalfi, and Ravello.

Each town offers dramatic views, charming streets, and delicious seafood. If you have time, make a stop in Sorrento, a town famous for its lemon groves and picturesque cliffs overlooking the Tyrrhenian Sea.

Day 4: Naples Museums and Departure to Rome

Before you head to Rome, spend your last morning in Naples visiting the National Archaeological Museum, which houses one of the best collections of Roman antiquities in the world, including many items from Pompeii and Herculaneum. You can also take a leisurely stroll along the Lungomare, the city’s seaside promenade, for a relaxed farewell to Naples.

In the afternoon, take the train to Rome—roughly a 1-2 hourjourney by high-speed train.

Days 4-7: Rome – The Eternal City

Next, head to Rome, the eternal city where ancient history and modern life converge. Whether you’re exploring ancient ruins, admiring Renaissance art, or enjoying a leisurely meal at a traditional trattoria, Rome never fails to impress. Fair warning, Rome is extremely crowded, but for good reason. It has some of the most famous sites in the world and they are not to miss but also do not be afraid to venture away from the tourist sites and get lost forging your own path through the ancient streets of Rome. You never know what you may come across. 

Day 4: Arrival and Ancient Rome

After settling into your hotel, start your Roman journey by heading to the iconic Colosseum, the ancient amphitheater where gladiators once fought. It is an extremely impressive historical monument one of the seven wonders of the world. There is the ability to go inside of it as well, it is extremely impressive though the lines to get in can take and hours. Plus, Rome gets very hot so if you want to see the inside, bring lots of water. I opted to go in and I really enjoyed it, though I do not think I would’ve felt as though I’d missed out if I just saw the outside of this ancient structure. Just a short walk away, you’ll find the Roman Forum and Palatine Hill, two of the most important archaeological sites in Rome. Don’t miss a visit to Capitoline Hill, which offers stunning views of the Forum. 

Try and venture away from this area to find some delicious Roman food as everything near the Colosseum will be significantly more expensive and touristy. 

Day 5: Vatican City and Baroque Rome

Start the day early at Vatican City, where you can visit St. Peter’s Basilica and marvel at the architecture and artwork inside. If you’re a fan of art, don’t miss the Vatican Museums, where you’ll find the famous Sistine Chapel, painted by Michelangelo. 

Again, be prepared for more long lines. These museums are the most impressive museums I have ever been to and well worth venturing inside if you have the time. In the afternoon, explore Piazza Navona, one of Rome’s most beautiful squares, known for its baroque fountains and cafes. From here, wander through the Pantheon, a well-preserved temple dedicated to the Roman gods.

Day 6: Piazza di Spagna and Villa Borghese

Spend the day visiting Rome’s more fashionable districts. Start at Piazza di Spagna (Spanish Steps), and then make your way to Villa Borghese, Rome’s central park, which houses the famous Galleria Borghese. The gallery has an impressive collection of sculptures and paintings, including works by Caravaggio and Bernini. By this point of my journey in Rome, I was getting sick of the crowds and wanted to escape, so I spent a few hours sitting in the park, enjoying the solitude and reading book. Villa Borghese is a massive park so it is easy to find a quiet corner for some alone time. 

In the afternoon, visit the Trevi Fountain and throw a coin in to ensure your return to Rome! End the day with a delicious dinner in the Trastevere neighborhood, one of Rome’s most vibrant districts.

Day 7: Final Morning in Rome and Train to Florence

On your final morning in Rome, spend time in Campo de’ Fioriand Piazza del Popolo for a leisurely breakfast and some last-minute shopping. In the afternoon, hop on a high-speed train to Florence (approximately 1.5 hours).

Days 7-10: Florence – The Cradle of the Renaissance

Florence, the birthplace of the Renaissance, is a city brimming with world-class art, architecture, and history. It’s the place to immerse yourself in Italian culture, from the iconic Duomo to the stunning masterpieces housed in the Uffizi Gallery.Florence, although still full of tourists, feels like a nice peaceful retreat after the hustle and bustle or Rome. It is a stunning city with so many beautiful sights and lots of beautiful parks. 

Day 7: Arrival and Historic Center

Upon arrival, take a leisurely walk around the Piazza del Duomo to admire the magnificent Florence Cathedral and Giotto’s Campanile. Don’t miss the Baptistery of St. John, known for its stunning bronze doors, also called the “Gates of Paradise.”

Day 8: Day Trip to Siena, San Gimignano and Pisa

Today’s adventure takes us to three of Tuscany’s most iconic spots: Siena, San Gimignano, and Pisa, all within a few hours’ drive of Florence.

I highly recommend getting outside of Florence for a day and seeing what else Tuscany has to offer. It is a beautiful region and one of the most famous wine regions in the world. I found a day trip that took me to Siena, San Gimignano and Pisa by bus with lunch at a winery included, but if you rented a car, it’s just as easy to mimic. It was an incredible day and if you can find something similar, I would suggest you do it.

First up, we head to Siena, a beautiful medieval city known for its Piazza del Campo, where the famous Palio horse race takes place. Be sure to visit the Siena Cathedral (Duomo), a gothic masterpiece with impressive artwork and an ornate interior. Wander the narrow streets and enjoy the city’s timeless atmosphere.

Next, we visit San Gimignano, a charming hilltop town with a skyline of medieval towers. It’s the perfect place to explore on foot, with cobblestone streets, local shops, and stunning views of the surrounding countryside. Don’t forget to try the famous gelato, often considered the best in the world!

Finally, we reach Pisa, home to the iconic Leaning Tower. Besides snapping the classic photo with the tower, explore the Piazza dei Miracoli, the Pisa Cathedral, and the Baptistry. If time permits, take a stroll along the Arno River or grab some gelato next to the Leaning Tower. 

By the time you return to Florence in the evening, you’ll have experienced the best of Tuscany, from Siena’s medieval streets to the unforgettable Leaning Tower of Pisa.

Day 9: Florence Museums and Ponte Vecchio

Today, visit the Galleria dell’Accademia to see Michelangelo’s iconic David. The Uffizi gallery is also an extremely famous gallery and popular amongst tourists, but I opted not to do this one as one art gallery was enough for me. The line and cost were lower for the Galleria dell’Accademia, plus I really wanted to see the David statue, so I opted for that one over the Uffizi. Feel free to choose whichever you prefer, or do both if you really love art. In the afternoon, head to the Boboli Gardens, a lush park filled with sculptures and fountains. The gardens offer a serene escape from the city and a stunning view of Florence.Afterward, wander along the Arno River and cross the famous Ponte Vecchio, the historic bridge lined with shops. In the evening, climb to the Piazzale Michelangelo for panoramic views of Florence. This is such a picturesque lookout. I tried to make the most of my time up here by grabbing a beer from a local merchant and drinking it while overlooking the incredible view while the sound of a busking violinist filled my ears with serene works from various classical composers. 

Day 10: Head to Venice

On your final morning in Florence, walk through the charming streets one last time and then make your way to the train station for another train ride, this time to Venice. 

Days 10-12: Venice – The City of Canals

Next, make your way to Venice, one of the most unique cities in the world. With its winding canals, historic palaces, and gondola rides, Venice is a magical place to explore. Seriously, there is nowhere else in the world like Venice. Venice deals heavily with overtourism, so expect extremely crowded streets, but if you are travelling offseason or somehow manage to find some quiet canals, slow down, take a deep breath and enjoy the beauty that is Venice. 

Day 10: Arrival and Grand Canal

Arrive in Venice and take your first walk along the Grand Canal, the city’s main waterway. A gondola ride or vaporetto (water bus) ride is a must to get a unique view of the city. Explore Piazza San Marco, home to the Basilica di San Marcoand the Doge’s Palace. I highly recommend heading to a grocery store and picking up an inexpensive bottle of wine and drinking it in a quiet spot along a canal with a bowl of Gelato as the sun sets over the canals. 

Day 11: Exploring Venice’s Islands

Take a day trip to the nearby islands of Murano, famous for its glassmaking, Burano, known for its colorful houses, and Torcello, a peaceful island with ancient ruins. Many people opt not to do this but I think its well worth the time. Taking the water taxi is a unique and exciting experience and the islands are much quieter than Venice is so it can be a very nice break from the noise. In the afternoon, return to Venice and visit the Rialto Bridge and the Market, then take a moment to relax at a café along the Grand Canal. Find a local restaurant for a romantic seafood dinner by the canal.

Day 12: Final Day in Venice, Verona and Departure to Milan

Leaving Venice marks one of my favourite days of my Italy trip, not because I disliked Venice, I absolutely loved it, but what was yet to come I would love even more. 

Start the day early with a short train ride from Venice to Verona, a city rich in history and romance. First stop: the iconic Arena di Verona, a Roman amphitheater that’s still used for performances today. Wander through Piazza delle Erbe, a vibrant square surrounded by medieval buildings, and don’t miss the Casa di Giulietta, where you can see Juliet’s balcony—a must for any Romeo and Juliet fan. Take a leisurely stroll along the Adige River or head to the Piazza dei Signori, where you’ll find beautiful sculptures and historic palaces. Enjoy lunch at a café with views of Verona’s charming piazzas or riverside. I spent the afternoon just reading a book along the Adige River in a quiet spot and enjoying the romance that filled the air of charming Verona. After soaking in Verona’s romantic charm, catch a train to Milan, just a 1.5-hour ride away. 

Day 12-14: Milan – The Fashion City

Milan, Italy’s fashion capital, offers a sharp contrast to the historic cities you’ve visited. With its sleek boutiques, cutting-edge architecture, and vibrant art scene, Milan is a modern and stylish city. Many people love Milan, but it was my least favorite spot along the trip. There are still plenty of things to see and do, but it lacked the charm of the other cities and felt like a big city that could be anywhere in the world. Maybe you’ll love it more than I will though.

Day 12: Arrival and Duomo di Milano

Arrive in Milan in the afternoon or evening, giving you a relaxed end to your stay. Depending on the time, you might have just enough energy to stroll over to the Duomo di Milano and marvel at its stunning Gothic architecture.

If you’re feeling up to it, take the elevator or climb the steps to the rooftop for amazing views of the city. Afterward, wander through the Galleria Vittorio Emanuele II, one of the world’s oldest shopping malls. It’s a great spot to people-watch and enjoy the Milanese atmosphere.

Day 13: Art and Fashion

Spend the day immersing yourself in Milan’s vibrant art and fashion culture. Begin with a visit to the Pinacoteca di Brera, where you can see works by Caravaggio, Raphael, and other renowned artists. For a more contemporary experience, head to the Fondazione Prada or Museo del Novecento to explore cutting-edge art.

Fashion lovers can’t miss the Quadrilatero della Moda, Milan’s famous fashion district. Here, you’ll find high-end boutiques and flagship stores from the world’s top designers. Whether you’re window-shopping or indulging in some retail therapy, this area showcases Milan’s fashion-forward flair.

Day 14: Time to Head Home

Take the last morning to unwind and explore Milan at a slower pace before heading to the airport and making your way home, wherever that may be.