Few places on Earth are as romanticized as Italy. It is the land of “la dolce vita,” the sweet life, an idyllic blend of cultural heritage, mouthwatering cuisine, and history that runs deep into the seams of the Old Country. Its cities combine ancient ruins with modern luxuries while boasting an array of unique experiences. In this list, I’ve compiled my picks for the seven most beautiful cities in Italy. If you’re planning a trip to everyone’s favorite country shaped like a boot, you can’t go wrong with these Italian vacation destinations.
The prettiest cities in Italy are as diverse as they are picturesque. From the centuries-old canals of Venice to the fashion-forward streets of Milan, there’s no end of things to look forward to when flying to Italy. Whether you’re looking to tour magnificent European churches or simply want to unwind in your own Italian rental villa, the possibilities are endless. Then again, with how popular the local cuisine is with tourists, maybe I should say “the pasta-bilities are endless.”
Jokes aside, I have to confess: I had a hard time narrowing this list down to just seven cities. Italy is home to many of the most beautiful cities in Europe, as well as the whole world. There are countless wonders here, both natural and man-made. Ultimately, the true beauty of Italy is in its rich diversity, culture, and rich historical heritage. Let the spirit of exploration whisk you away to the seven most beautiful cities in Italy… and beyond!
How to save money flying to the most beautiful cities in Italy
Looking to visit the best cities in Italy? Then you’ll want to heed these insider tips on how to save BIG on airfare.
International travel is often expensive, but it doesn’t have to be. As a serial traveler, I know how important it is to make every penny count. That’s why I always use Scott’s Cheap Flights (now called Going) when buying airline tickets.
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Most beautiful cities in Italy: 7 must-see Italian vacation spots
Few countries on Earth can compete with Italy in terms of sheer gorgeousness. It’s a place where natural landscapes, centuries-old monuments, and elegant modern villas come together in a way that is truly special. Here are my picks for the seven most beautiful cities in Italy.
1. Florence
The birthplace of the Renaissance, Florence isn’t just one of the most beautiful cities in Italy. It’s also one of the most as intellectually stimulating. Known as Firenze in the native tongue, it’s a symphony of red-tiled rooftops, majestic cathedrals, and world-renowned art. To say it’s humbling to walk the same cobbled streets as Michelangelo, Dante, and Leonardo da Vinci is an understatement.
Florence is home to a treasure trove of iconic landmarks. Arguably none are more famous than the Duomo, a masterpiece of Gothic and Renaissance architecture. Its adjacent bell tower, designed by Giotto, offers breathtaking panoramic views of the city. The Uffizi Gallery, another must-visit, houses an impressive collection of Renaissance art, including works by Botticelli, Caravaggio, and Da Vinci.
Beyond the sights, visitors can delve deeper into Florentine culture. Take a leisurely stroll across the Ponte Vecchio, the oldest bridge in the city filled with glittering jewelry shops. Sample the hearty Tuscan cuisine, a true testament to the Italian love for fine food. Try the famous Florentine steak, sip on a glass of Chianti, and treat yourself to a scoop of gelato from one of the city’s numerous gelaterias.
Interested in souvenirs? You can explore traditional workshops in the Oltrarno district where skilled artisans continue centuries-old crafts like bookbinding and mosaic-making. The beauty of Florence lies not just in its architectural grandeur or its priceless art, but in its spirit. A few days in the city, and you’ll definitely want to bring that spirit home with you.
2. Rome
The “Eternal City” of Rome is a fascinating mélange of the ancient and the modern. This vibrant metropolis carries the weight of over two millennia of history. It’s a tale told via colossal monuments, enduring traditions, and lively piazzas. Rome is a city that effortlessly merges its centuries-old legacy with a bustling contemporary culture.
Few places in the world can compete with Rome’s historical significance. The city was the heart of one of the world’s greatest civilizations, the Roman Empire. The indelible mark of that history can be witnessed everywhere. From the mighty Colosseum, where gladiators once fought, to the stately Roman Forum, the whole city is one big open-air museum.
Within Rome is Vatican City, the world’s smallest independent state. Here you’ll find awe-inspiring religious sites like Saint Peter’s Basilica and the Sistine Chapel. The sight of Michelangelo’s painted ceiling is a spectacle that needs to be seen to be believed. Afterward, delve into the heart of the city to experience la dolce vita. Engage in the lively atmosphere of Piazza Navona and the Spanish Steps.
To cap the evening, you can indulge in a late-night dinner of traditional Roman fare, like carbonara or suppli. For discerning foodies, Rome offers an exquisite culinary scene that ranges from traditional trattorias to contemporary fine dining. Sample a slice of pizza bianca, delight in a scoop of tiramisu, or wander the markets in search of fresh, local produce and homemade specialties. In addition to being one of the most beautiful cities in Italy, Rome is also one of the tastiest!
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3. Venice
To the people of Italy, Venice is more than just a beautiful Italian vacation spot. It’s La Serenissima, the “Most Serene.” This city of water, as it is often called, is a labyrinth of canals, bridges, and islands that combine to form an urban landscape that seems more like a dream than reality. Comprising more than 100 small islands in a lagoon in the Adriatic Sea, Venice is a testament to the ingenuity of the past and the romantic allure of the Old Country.
Imagine navigating through a maze of narrow waterways in a traditional gondola. As the city’s historic buildings rise from the water’s edge, their majestic facades are reflected in the shimmering canals. Picture the grandeur of St. Mark’s Square, dominated by the awe-inspiring, soaring Campanile. All the while, hundreds of years of commerce reverberate through the historic Rialto Market.
Visit the iconic Doge’s Palace, a stunning example of Venetian Gothic architecture. Marvel at the masterpieces housed in Gallerie dell’Accademia, offering a comprehensive collection of Venetian art from the 14th to the 18th centuries. Experience the centuries-old tradition of Murano glassmaking, witnessing how molten glass transforms into intricate works of art.
Venice isn’t just about the past, mind you. It’s a living, breathing city with a vibrant culture and an enduring spirit. Travelers can taste the freshness of the sea in classic Venetian cicchetti, a local style of tapas. Depending on the time of year, you may also wish to take part in one of the city’s many festivals. Most famous is the annual Carnevale, when the city transforms into a spectacle of masks and merriment. It’s truly a unique experience, one that engages all your senses and leaves an unforgettable impression.
4. Milan
The second-largest city in Italy (and also one of the most beautiful cities in Italy) is Milan. A powerhouse of fashion, design, and contemporary culture, it is a city that thrives on innovation and glamour. As such, the allure of Milan is different from the antiquated charm of Rome or the romantic appeal of Venice. This is a city where the past and future collide, creating an atmosphere that’s distinctly cosmopolitan and quintessentially Italian.
A symbol of Milan’s rich past and present is the Duomo di Milano. This gorgeous cathedral, one of the largest in the world, boasts an intricate Gothic façade and a panoramic view from its rooftop. Not far from the Duomo, the Galleria Vittorio Emanuele II, one of the oldest shopping malls in the world, exemplifies the luxurious side of Milan.
Milan’s soul lies in its trend-setting modernity. As a global capital of fashion and design, the city is home to leading designer stores, avant-garde boutiques, and the influential Milan Fashion Week. In the trendy Brera district and the vibrant Navigli area, you’ll find an array of chic restaurants and bars. Here you can indulge in Milanese specialties like risotto alla Milanese or the traditional aperitivo.
To delve deeper into Milan’s contemporary culture, visit the ultra-modern district of Porta Nuova, characterized by sleek skyscrapers and green spaces. For art lovers, the Fondazione Prada, a modern art institution, offers innovative exhibitions in a former gin distillery transformed into a stunning contemporary space. A visit to Milan offers an intoxicating taste of Italy’s stylish side. Indeed, in Milan, you’ll find that style is not just about fashion, but a way of life.
5. Naples
The city of Naples (or Napoli, as the locals call it), sits against the stunning backdrop of Mount Vesuvius, overlooking the azure waters of the Tyrrhenian Sea. No wonder, then, that Naples has inspired artists, writers, and dreamers for centuries. This dynamic city is full of life, color, and character, making it one of the most beautiful cities in Italy, bar none.
The spirit of Naples lies in its teeming streets, its bustling markets, and its vibrant neighborhoods, each with its distinct character. Wander around the historic center, a UNESCO World Heritage site, with its narrow alleyways packed with baroque churches, ancient chapels, and bustling piazzas. Visit the grand Piazza del Plebiscito, surrounded by the Royal Palace and the Basilica of San Francesco di Paola, reflecting the city’s centuries-old glory.
History buffs will be thrilled by Naples’ wealth of archaeological sites. The National Archaeological Museum hosts an extensive collection of Greco-Roman artifacts, including mosaics, sculptures, and treasures from Pompeii and Herculaneum, two ancient cities preserved under volcanic ash from the eruption of nearby Mount Vesuvius.
Of course, no tour of Naples would be complete without sampling culinary delights. Naples is the birthplace of pizza, after all. Try a traditional Neapolitan pizza, enjoy a sfogliatella pastry, or savor a creamy gelato. Visit the bustling fish markets in the morning, enjoy an espresso at a sidewalk café, or join the lively crowds at a local trattoria in the evening. The city’s beauty is as fiery as Mount Vesuvius and as flavorful as the city’s famed pizza. It’s a slice of heaven here on Earth!
6. Verona
Widely known as the setting for Shakespeare’s “Romeo and Juliet,” Verona is a city that exudes culture and sensuality. Nestled along the Adige River, Verona is one of the most beautiful cities in Italy with its medieval pink-hued buildings, Roman ruins, and Renaissance palaces. Its well-preserved architecture and the lyrical quality of its streets and squares make Verona a city that both enchants and inspires.
Verona’s historic heart is its Arena, a Roman amphitheater remarkably well-preserved and still used today for operatic performances. Indeed, walking through Verona is like stepping into a different era. Piazza delle Erbe, the city’s bustling marketplace, is ringed with medieval buildings and lively cafés.
Not far from here is Juliet’s House, where the famous balcony scene from Shakespeare’s tragedy is set. Although Juliet was a fictional character, the house is a real place that inspires lovers from around the world who inscribe their names on its walls as a testament to their affection.
Don’t miss the opportunity to explore the city’s artistic side at the Verona City Museum, located in a fortified castle, Castelvecchio. The museum houses a valuable collection of medieval and Renaissance art and offers stunning views of the city from the castle’s ramparts. Beyond the city, the rolling vineyards of the Valpolicella wine region and the shimmering waters of Lake Garda are perfect for day trips. Like a star-crossed Montague courting a forbidden Capulet, you’re sure to fall in love with the city of Verona
7. Siena
An epitome of medieval grace, Siena is a city where time stands still. Located deep in the heart of Tuscany, Siena is known for its stunning architecture and storied traditions. Siena’s narrow winding streets and grand palaces exude a timeless wonder that makes it easily one of the most beautiful cities in Italy.
Siena locals often gather in the shell-shaped Piazza del Campo, widely regarded as one of Europe’s greatest medieval squares. The square, with its distinctive nine segments, symbolizes the Nine Guilds that governed the city in the Middle Ages. It is in this very square that the historic Palio horse race takes place twice a year, an event that infuses the city with infectious enthusiasm and pulse-pounding excitement.
Towering over the square is the imposing Palazzo Pubblico and its graceful bell tower, Torre del Mangia. Climb to the top of the tower for an unparalleled view of Siena’s red-tiled rooftops and the surrounding Tuscan countryside. The Palazzo also houses the Civic Museum, showcasing stunning frescoes that portray profound allegories of good and evil.
Just a short walk away is the majestic Siena Cathedral, a stunning example of Italian Romanesque-Gothic architecture. Step inside to discover the intricate floor mosaics, the striking pulpit, and the Piccolomini Library adorned with vibrant frescoes. Afterward, take a leisurely stroll along the medieval streets. Or, dine in traditional trattorias and savor the flavors of the region’s cuisine, paired with exceptional Tuscan wines. The only thing more intoxicating than the vino is the charm of the city itself.
Frequently asked questions (FAQ) about the most beautiful cities in Italy
Italy is a big country with lots to see and do. It helps to be prepared. To help you plan ahead, I’ve compiled some of the most frequently asked questions I’ve received about Italy’s most beautiful cities, along with their answers. With the information here, there’s no reason you’re Italian getaway can’t be one for the ages.
What city is the prettiest in Italy?
While beauty is subjective and every city in Italy possesses its own charm, one city stands out as the prettiest: Florence.
Known as the birthplace of the Renaissance, Florence exudes elegance, artistry, and architectural marvels at every turn. From the iconic Duomo with its magnificent dome to the enchanting Ponte Vecchio, a bridge adorned with jewelry shops, Florence offers a breathtaking showcase of artistic heritage.
Stroll through the cobblestone streets, soak in the ambiance of Piazza della Signoria, and immerse yourself in the beauty of masterpieces at the Uffizi Gallery. While Italy’s beauty knows no bounds, Florence’s timeless allure and captivating aesthetics make it the prettiest Italian city.
How can I save money visiting the most beautiful cities in Italy?
Italy is a country known for its stylishness and luxury. That doesn’t mean Italy’s most beautiful cities have to be its most expensive cities, though. There’s no reason you can make every penny count with a little planning. Here are some travel hacks for saving money on trips to Italy:
- Look for budget-friendly accommodations like hostels, guesthouses, or vacation rentals. Consider staying in less touristy areas or booking in advance for better rates.
- Use public transportation, such as trains or buses, which are often cheaper than taxis. Consider purchasing regional or city-specific transportation passes for discounted fares.
- Opt to dine at local eateries and trattorias instead of overpriced touristy restaurants. Take advantage of fixed-price lunch menus and indulge in street food to save money on meals.
- Research free or discounted attractions, museums, or tours available. Many of the most beautiful Italian cities offer tourist cards that include free or discounted entry to multiple attractions.
- Explore local markets for affordable souvenirs and fresh produce. Avoid touristy shops near popular landmarks, as they tend to be pricier.
- Avoid currency exchange services at airports or tourist areas, as they often have high fees. Instead, withdraw money from ATMs or use credit cards with low foreign transaction fees.
- When booking a flight, be flexible with your travel dates and consider alternate airports to find the best airfare deals. Most importantly, remember to sign up for free email alerts from Going (formerly Scott’s Cheap Flights). This will ensure the best travel deals to Italy are sent right to your inbox. If you travel often, you can save even more money by upgrading to the Premium version or the Elite version for a small annual fee. Use my coupon code JON20 to save 20% when you join.
What is the best time to travel to Italy’s most beautiful cities?
The best time to visit Italy is during the spring (April to June) or fall (September and October) when the weather is pleasant, and tourist crowds are smaller. However, Italy’s beauty can be appreciated year-round.
Keep in mind that certain cities can be particularly busy during specific events, like Venice during Carnevale. If possible, try to avoid going during the peak season (July through August). Summer tourism leads to larger crowds and higher prices.
How do I travel between the most beautiful Italian cities?
Italy’s extensive rail network makes it easy to travel between these cities. High-speed trains connect major cities like Rome, Florence, and Milan. For cities like Venice and Siena, regular trains are available. Rental cars are also an option if you prefer driving, and they allow more flexibility to visit the countryside and smaller towns.
What is the best walkable city in Italy?
When it comes to walkability, the city that takes the crown in Italy is none other than Florence. Known for its compact size and pedestrian-friendly streets, Florence invites visitors to explore its historic center on foot.
The Italian city’s treasures, from the iconic Duomo and Uffizi Gallery to the charming Ponte Vecchio and bustling Piazza della Signoria, are easily accessible within a leisurely stroll.
Immerse yourself in the enchanting atmosphere, wander through the winding cobblestone lanes, and uncover hidden gems around every corner. With its walkable layout and abundance of architectural and artistic wonders, Florence offers a truly immersive and cool experience for those seeking to explore Italy on foot.
Is English widely spoken in Italy’s most beautiful cities?
Yes, English is commonly spoken in most tourist areas, hotels, and restaurants. However, learning a few basic Italian phrases is appreciated and can enrich your travel experience.
I recommend using a language education service like Duolingo. In addition to being one the best travel apps for iPhone and Android right now, it’s a convenient and easy-to-use tool that you can take with you everywhere you go.
Are the most beautiful cities in Italy suitable for families?
Absolutely. Every city mentioned in this post offers a range of attractions and activities suitable for families with children. These include historical sites, parks, gelato shops, and pizza places. Italian culture has a distinctly positive and inclusive view of children. This means that families are always welcome and most businesses are happy to accommodate them.
That said, if you are concerned about whether a particular activity or attraction is appropriate for your child, it helps to plan ahead. Consider calling before you go. Most proprietors will be happy to inform you of any age restrictions or sensitive content you’re likely to encounter. Don’t be afraid to ask!
What are the best cities to go to in Italy?
Italy offers a myriad of incredible cities to explore. Among the best, three stand out as must-visit destinations.
Rome, the Eternal City, captures the essence of Italy with its awe-inspiring ancient ruins. This includes the Colosseum and Roman Forum, as well as the grandeur of St. Peter’s Basilica and the Vatican City.
Venice, a floating masterpiece, enchants visitors with its romantic canals, exquisite palaces, and the iconic St. Mark’s Square. Getting lost in the labyrinthine streets and sailing along the picturesque canals on a gondola is an unforgettable experience.
Lastly, Florence, the birthplace of the Renaissance, beckons art enthusiasts with its world-class museums and galleries, showcasing masterpieces like Michelangelo’s David and Botticelli’s Birth of Venus. The city’s architectural wonders, such as the Duomo and Ponte Vecchio, add to its allure.
These three cities of Italy represent the country’s rich history, artistic heritage, and architectural splendor. As such, it makes them among the best Italian cities to visit in 2023.
