Italy is a country that truly has it all, from stunning coastlines and islands to majestic mountains perfect for skiing. Yet, as much as I love exploring the countryside, my heart always returns to its vibrant cities. They each offer something so wonderfully different, a testament to Italy’s rich history and diverse regions. I’ve had the pleasure of living in Rome for over five years now, and with every chance I get, I venture out to discover more. What I find so captivating is how a drive of just an hour or two can transport you to a place with a completely new feel. Some cities will simply leave you in awe with their ancient treasures, while others will inspire you with their modern fashion and innovative design. One thing is certain wherever you go in Italy: the food is always incredible, especially when you seek out the local specialties, which change from place to place.
It’s tempting to try and cram as many cities as possible into a single trip, especially if you have limited time. But from my experience, and with two little ones in tow, these cities each deserve at least two or three days to truly begin to appreciate them – and even then, you’ll only have scratched the surface. Whether this is your first visit or you’re a seasoned traveler, here are some of the Italian cities that I believe are absolutely essential for any itinerary.
Rome
Rome, the Eternal City, is often the gateway for many visitors to Italy, and it’s easy to see why. With its history spanning over 2,000 years, this city, which has been recognized with a World’s Best Award, offers an endless array of things to see and do. For anyone visiting for the first time, ticking off the Colosseum and the Vatican is a must. But beyond that, Rome is a place to wander, to discover hidden piazzas, and to simply soak in the atmosphere. I often encourage families to find a quiet spot near an ancient aqueduct for a picnic, or to explore the courtyards of old palaces. And of course, the food is a huge part of the experience – don’t miss out on pastas like carbonara and cacio e pepe. It truly feels like a city you could spend a lifetime exploring.
When Michael and I first brought Lily and Ethan here, we learned that navigating Rome with young children requires a bit of strategy. The key is to break up the days and not try to see everything at once. We found that visiting popular sites early in the morning, before the big crowds arrive, made a huge difference. For instance, we’d head to the Colosseum right after breakfast, and then find a park or a gelato shop to let the kids burn off some energy before our next activity. Trying to see the Vatican Museums and St. Peter’s Basilica in one go with little ones can be overwhelming. We usually split it up, perhaps doing the museums one day and St. Peter’s the next, focusing on just a few key areas within the museums to avoid sensory overload for them.
Florence
Florence, widely celebrated as the birthplace of the Renaissance, consistently ranks as one of Europe’s top cities by travelers. The sheer concentration of artistic and architectural masterpieces here is astonishing. You can marvel at Michelangelo’s David at the Galleria dell’Accademia, witness Botticelli’s “Birth of Venus” at the Uffizi Gallery, and admire the magnificent Duomo, all within a single day. Stepping across the famous Ponte Vecchio leads you to the Oltrarno district, a charming area filled with artisan workshops, vintage boutiques, and cozy cafes and restaurants. For a taste of Tuscany, be sure to sample local specialties like panzanella, pappa al pomodoro, and the renowned bistecca alla Fiorentina, perhaps paired with a glass of Chianti.
With Florence, especially around the Duomo and the Uffizi, the crowds can be substantial. I’ve learned that booking tickets well in advance is essential, particularly if you’re traveling during peak season. For families, I always recommend looking for guided tours that are specifically designed for children. These tours often make the art and history come alive in a way that engages younger minds, turning a potentially long museum visit into an adventure. We once took a “secret passages” tour near the Ponte Vecchio, and my kids were fascinated by the stories of old merchants and hidden tunnels. It’s those kinds of experiences that make the history feel so real and accessible for them.
Venice
Venice, often called La Serenissima, meaning “the most serene,” is a city that truly captivates everyone who visits. Simply wandering through its maze of canals, watching the gondolas glide by as they pass by ornate Renaissance palaces, is an experience like no other. St. Mark’s Basilica, the Doge’s Palace, and the Galleria dell’Accademia are just a few of the historical highlights. Venice also hosts vibrant events like the Venice Biennale and Carnevale. However, the sheer volume of visitors can sometimes be overwhelming, which is why I often suggest visiting during the shoulder seasons, from November through March, to enjoy a more peaceful experience.
Navigating Venice can feel a bit bewildering at first because there aren’t really “streets” in the way we’re used to. It’s all about canals and narrow alleyways. For families, this can be an adventure in itself! I always tell people to wear comfortable shoes because you’ll be doing a lot of walking, and it’s easy to get turned around. A common mistake is relying solely on maps; sometimes just embracing the labyrinthine nature of the city and allowing yourself to get a little lost can lead to the most wonderful discoveries. We once stumbled upon a tiny mask-making workshop where Ethan got to try painting his own souvenir, which was a highlight for him. Also, be mindful of the vaporetto (water bus) schedules and routes; they are your main mode of public transport and can get very crowded.
Milan
Milan, Italy’s hub for fashion and design, often gets overshadowed by the country’s more art-focused cities, but it absolutely deserves a spot on your list. As Italy’s most international and cosmopolitan city, it’s a dynamic place with an exceptional restaurant and bar scene, arguably the best in the country. Must-do experiences in Milan include admiring the stunning Duomo and the Galleria Vittorio Emanuele II, enjoying a Negroni sbagliato at the very bar where it was invented, and visiting the Prada Foundation and Villa Necchi Campiglio. Be sure to try local classics like risotto alla Milanese and cotoletta alla Milanese.
When we visited Milan, I was struck by how seamlessly high fashion and historic architecture coexisted. The energy of the city is palpable. For families, a visit to the Duomo is a must, but climbing to the rooftops for the views is an experience kids often find absolutely thrilling. The intricate details of the spires up close are incredible. One practical tip: the area around the Duomo can be very busy, so keeping a close eye on the children is important, especially when crossing the tram lines. We learned this the hard way and had a close call – always be aware of your surroundings and the movement of both pedestrians and vehicles.
Naples
Many travelers pass through Naples on their way to the stunning Amalfi Coast, Capri, or Ischia, but this vibrant city, the birthplace of pizza, is a destination in its own right. An old Italian saying, “Vedi Napoli e poi muori” (“See Naples and then die”), suggests that Naples is the ultimate experience. While the city might have a reputation for being a bit gritty and chaotic, it’s also home to a magnificent archaeological museum and breathtaking works by Caravaggio. Its tailors are also celebrated as some of the finest in Italy. Beyond indulging in authentic Neapolitan pizza, be sure to taste local specialties like sfogliatella.
Naples has a soul that’s utterly unique. It can feel intense at first, with its bustling streets and lively markets. I remember our first walk through the Spanish Quarter – it was an explosion of colors, sounds, and smells! For families, navigating these lively streets requires a good dose of patience and awareness. We found that embracing the chaos was part of the charm. One thing that surprised me was how much my kids enjoyed just watching the daily life unfold, the scooters whizzing by, the vendors calling out. It’s a very different pace than what they’re used to. A common mistake for visitors is to be put off by the initial energy; my advice is to dive in, and you’ll find an incredibly warm and welcoming city. And, of course, the pizza is an absolute must-try; finding a small, local pizzeria is always the best bet.
Bologna
Bologna is a city with three fitting nicknames: La Dotta (“The Learned”), La Grassa (“The Fat”), and La Rossa (“The Red”). “The Learned” refers to its university, the oldest in Europe, founded in the 11th century. “The Fat” alludes to the city’s incredibly rich and hearty cuisine; tagliatelle alla Bolognese, lasagna, and tortellini all originate from this culinary capital. “The Red” may reference the characteristic color of its medieval brick buildings or the city’s historical political leanings. Regardless of the interpretation, Bologna stands out as one of Italy’s most liberal, educated, and gastronomically celebrated cities.
Bologna is a food lover’s paradise, and honestly, that’s what drew me here initially. Michael and I love exploring the Mercato di Mezzo, a vibrant indoor market where you can sample so many local delicacies. With Lily and Ethan, it’s a fantastic place to introduce them to new flavors without the pressure of a formal meal. They can try different cheeses, cured meats, and of course, pasta. A common pitfall for visitors is to assume that “Bolognese sauce” is the same everywhere; in Bologna, it’s typically served with tagliatelle or other fresh pasta, and it’s a rich, slow-cooked ragù. Don’t be afraid to try the tortellini in brodo (broth), especially during cooler months; it’s a comforting and classic dish. We found that the arcades, or porticoes, that cover much of the city are a lifesaver, especially if you encounter unexpected rain or strong sun, offering covered walkways for strolling and exploring.
Palermo
Palermo, the capital of Sicily, showcases a captivating blend of Arab, Norman, Byzantine, and Baroque architectural influences, a legacy of the diverse cultures that have ruled the island. This rich history is evident in its main cathedral and the Palatine Chapel, a stunning example of mosaic artistry. When visiting Palermo, exploring the bustling outdoor markets like Ballarò and Vucciria is a must. Here, you can savor street food specialties such as arancini and cannoli. Despite its lively and sometimes chaotic atmosphere, Palermo is known for its incredibly open and hospitable people.
The energy in Palermo is infectious. It’s a city that engages all your senses. The markets are an absolute must for experiencing the local culture and, of course, the food. I remember the first time we took the kids to the Ballarò market; the sheer volume of produce, spices, and vendors calling out was an adventure in itself for them. It’s a good idea to have cash on hand for market purchases. A common mistake visitors make is to be intimidated by the lively street scenes. My advice is to embrace it, wander through the stalls, and sample the incredible street food. For families, it’s a great way to experience authentic Sicilian flavors in a casual setting. Just be aware of your surroundings, as you would in any busy market.
Lecce
Often referred to as the “Florence of the South,” Lecce is gaining recognition among discerning travelers. Situated in Puglia, the heel of Italy’s boot, this charming city is characterized by its stunning Baroque architecture, which often takes on a warm, golden hue due to the local limestone used in its construction. The historic center is a delightful maze of narrow lanes lined with boutiques, bars, and restaurants. While in Lecce, be sure to try local specialties such as caffè Leccese (an iced espresso sweetened with almond syrup) and pasticciotti (traditional oval pastries filled with a creamy custard). Lecce also serves as an ideal base for exploring the beautiful beaches of the Salento Peninsula.
Lecce’s architecture is truly breathtaking, especially the way the stone seems to glow in the sunlight. When we first arrived, I was captivated by the intricate details of the Baroque facades. For families, the compact historic center is quite walkable, making it easy to explore without constant hopping in and out of cars. A common pitfall is not allowing enough time to simply wander and admire the buildings. We found that the best experiences happened when we let ourselves get a little lost in the charming side streets. Also, finding a local pasticceria for a morning pasticciotto is a delightful ritual. Be sure to try the caffè Leccese; it’s a refreshing treat, especially on a warm day.
Turin
As the capital of Piedmont, Turin is one of Italy’s quietly elegant cities. Ruled by the French Savoy dynasty for roughly 500 years, Turin holds the distinction of being the first capital of the unified Kingdom of Italy in 1861, and the Royal Palace of Turin is a significant historical landmark worth visiting. Travelers today can still detect a distinct French influence in the city’s architecture and culinary traditions. Before departing, savor prized wines like Barolo and Barbaresco, and indulge in local specialties featuring hazelnuts and truffles. Turin is also recognized as the birthplace of Vermouth.
Turin offers a sophisticated yet relaxed atmosphere. The wide avenues and elegant piazzas give it a grand feel, reminiscent of its aristocratic past. For families, the Egyptian Museum is world-renowned and can be a fascinating experience, offering a different kind of history than what’s typically found in Italy. I always advise booking tickets for popular attractions here, as they can fill up. A common mistake is overlooking the sheer quality of the pastries and chocolates here; Turin is a UNESCO City of Chocolate for a reason! We discovered a wonderful little cafe near the Piazza San Carlo where the kids had their fill of hot chocolate and I enjoyed a perfectly crafted bicerin (a layered coffee drink). The city is also very flat in the center, making it easy for strollers and little legs to get around.
Perugia
Umbria, often called Italy’s “green heart,” is a region in central Italy nestled between Rome and Tuscany. Its capital, Perugia, is a small yet charming city that retains much of its medieval character, making it an ideal destination for history enthusiasts. Inside the Palazzo dei Priori, you can admire frescoes by Perugino in the Collegio del Cambio. For a taste of Umbrian cuisine, opt for dishes like hearty pasta with wild boar ragu or fresh pasta with shaved black truffle. Perugia is also famous for its chocolate, so be sure to visit an artisanal shop, like Augusta Perusia.
Perugia feels like stepping back in time, and the views from the city walls are simply spectacular. The historic center is perched on a hill, so prepare for some uphill walking, but it’s well worth the effort. For families, the chocolate connection is a big draw. Ethan was absolutely thrilled to visit a chocolate shop and learn about how they make different confections. Using the escalators that run through the rock to get up to the upper parts of the city is a unique experience the kids will remember. A common mistake is not wearing comfortable shoes; the cobblestones can be uneven, so good footwear is essential. Trying the local Umbrian pasta dishes is a must, and don’t forget to sample some of the region’s excellent olive oil, which is some of the best in Italy.
Parma
Located just about an hour from Bologna, Parma defies expectations, offering immense cultural and culinary significance for its size. This is the birthplace of Parmigiano Reggiano cheese and prosciutto di Parma, making it a place where food is taken with utmost seriousness. During its time as a Duchy, Parma was exceptionally wealthy and powerful, leaving behind a legacy of artistic and architectural treasures. You can explore these at the Palazzo della Pilotta complex, which houses the National Gallery, the Farnese Theater, the Palatine Library, the Archeological Museum, and the Bodoni Museum, dedicated to Italy’s oldest printing museum.
Parma is a city that truly celebrates its culinary heritage, and it’s a wonderful place to explore with children. The focus on quality ingredients is evident everywhere. We found that visiting a local producer of Parmigiano Reggiano or prosciutto was incredibly educational and delicious. For families, the Palazzo della Pilotta is a fascinating area; the Teatro Farnese, with its impressive wooden structure, always sparks imagination. A common pitfall is visiting Parma and not fully immersing oneself in the food culture. Don’t just eat; learn about the traditions. We loved visiting a local market and seeing all the regional products. It’s a compact city, so getting around is quite easy on foot, and the children appreciate the slower pace.
Ready to plan your Italian adventure? These cities are just the beginning of what this incredible country has to offer. Let these glimpses inspire your own explorations and create unforgettable memories for your family!