I’ve wandered Italy from the snowy peaks of the Alps to the sunny cliffs of the Amalfi Coast, but these seven cities hold a special place in my heart. I’ve stood on Florence’s Piazzale Michelangelo, and I’ve felt the hum of history under my feet in Rome’s Forum. Venice swept me away with its quiet back canals, Milan impressed me with its sophisticated style, and Naples challenged me in all the best ways with its raw energy and unbeatable pizza. In Verona, I found myself spending hours on the Adge river, and in Siena, I was mesmerized by the rhythm of the city’s medieval streets.
I’ve been lucky enough to visit each of these cities more than once, and every time, I see something new. Beauty in Italy isn’t just in the architecture. It’s in the way these places make you feel and remind you what it means to live the dolce vita.

How to save money flying to the most beautiful cities in Italy
Want to explore Italy’s top cities without overspending on flights? I’ve got your back. Even international airfare doesn’t have to break the bank. That’s why I trust Going.com (formerly Scott’s Cheap Flights) to score unbelievable flight deals.
Going sends curated flight alerts straight to your inbox…deals on flights to beautiful destinations like Rome, Florence, Venice, and beyond. And these aren’t just average deals: members save an average of $550 on economy tickets, sometimes getting deals slashed 40–90 % off market value.
Here’s how it works:
- Sign up on Going.com for free.
- Pick your home airport.
- Relax…Going’s team and algorithms will hunt down deals, including rare mistake fares.
- Enjoy alerts tailored to your departure airport, so you’re only seeing flights that matter to you.
Want even better perks? Upgrade to Premium or Elite. Premium is about $49/year, Elite around $199/year, and both unlock earlier alerts, mistake fares, and better-class deals. As a creator, I’ve saved thousands using Going…now it’s your turn. Use code JON25 to get 25 % off your Going membership when you upgrade.
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.
Before you book anything, don’t miss these deals 👇
- ✈️ Find cheap flights you won't see on Google - Going.com saves me $200+ per ticket
- 🏨 Book your stay – The best 2025 deals on boutique hotels and vacation homes
1. Florence
The birthplace of the Renaissance, Florence isn’t just stunning to look at – it’s probably the most intellectually stimulating city break you’ll ever take. I’ve been back here three times, and honestly, walking the same cobbled streets as Michelangelo and Leonardo da Vinci never gets old.
The Duomo is obviously the main event, and climbing Brunelleschi’s dome is absolutely worth the €30 (that’s the 2025 price for the full Brunelleschi Pass). You’ll tackle 463 steps with no elevator, but the panoramic views over those famous red-tiled rooftops are incredible. Pro tip: book your climb for 8:15 AM – fewer crowds and better photos. The pass also gets you into Giotto’s Bell Tower, the Baptistery, and the Opera del Duomo Museum, all valid for three days.
The Uffizi Gallery requires advance planning (seriously, don’t wing this one). Standard tickets are around €25-30 for skip-the-line access, but they sell out 2-3 weeks ahead during peak season. I spent four hours there last time and barely scratched the surface. Botticelli’s Birth of Venus is worth the hype, but make sure you hit the terrace on the third floor – they actually have a café up there with killer views of the Arno River.
Don’t miss the Ponte Vecchio at sunset when the jewelry shops catch the golden light. The Oltrarno district is where you’ll find authentic artisan workshops doing bookbinding and mosaic work – way cooler than the tourist stuff near the Duomo. For food, skip the overpriced spots near major attractions and head to the covered Mercato Centrale for incredible Tuscan steak and local wine.

2. Rome
Rome is basically one giant outdoor museum, and after five visits, I’m still finding hidden gems. The Colosseum now costs €18 (including Roman Forum and Palatine Hill – same ticket covers all three), but booking ahead is essential since they cap daily visitors at 3,000. I always recommend the morning slots before 10 AM to beat the crowds.
The Vatican Museums are a different beast entirely. Skip-the-line tickets run about €29-35 in 2025, and trust me, you’ll use every second of that fast-track access. The lines for regular tickets can hit three hours in summer. The Sistine Chapel is obviously the headline act, but don’t rush through the Raphael Rooms and Gallery of Maps to get there.
St. Peter’s Basilica is free to enter, but the security lines are brutal. If you’re doing a guided Vatican tour (around €50-65), many include skip-the-line access to the basilica too. The dome climb is separate – €10 by elevator or €8 if you take the stairs (still 320 steps after the elevator).
Here’s what most tourists miss: Roman pizza al taglio is completely different from Neapolitan pizza, and it’s actually better for wandering around. Grab a slice near Campo de’ Fiori or Trastevere. The Pantheon is still free (for now), and it’s genuinely mind-blowing that this 2,000-year-old building is still standing perfectly intact.
✈️ Pro Travel Tip:
I use Going.com to find crazy flight deals...($300 roundtrip to Europe kind of crazy).
It’s free, and I honestly check it more than Google Flights. For a limited time only, they are offering 25% off on Premium and Elite to readers of my website, using my special code: JON25)

3. Venice
Venice is touristy as hell, but once you get past that, it’s pure magic. I learned this the hard way – St. Mark’s Square and the Rialto Bridge are beautiful but absolutely packed. The real Venice happens in the quieter sestieri like Cannaregio and Dorsoduro.
Gondola rides are pricey but honestly worth doing once. Official rates are €80 for 30 minutes during the day, €100 after 7 PM. You can fit up to six people in one gondola, so split the cost if you’re traveling with others. The touristy stations near St. Mark’s Square are crazy busy – I prefer boarding near Campo Santa Maria Formosa or the Jewish Ghetto for a more peaceful experience.
St. Mark’s Basilica requires timed entry (it’s free but you need to book online), and the security lines move slowly. Doge’s Palace is €28 and absolutely worth it – the Bridge of Sighs views from inside are way better than from the street. Combo tickets for multiple attractions start around €35.
The Murano and Burano day trip is a must if you have time. The islands are gorgeous, and watching glassblowing in Murano is surprisingly fascinating. I spent three hours on Burano just photographing the colorful houses and eating the best seafood risotto of my life.
Skip the overpriced restaurants near major sights. Head to Osteria alle Testiere for incredible seafood or any bacaro for cicchetti (Venetian tapas). The locals eat standing up at the bar – when in Venice, do as the Venetians do.

4. Milan
Milan surprised me. I expected all fashion and business, but the Duomo is genuinely one of the most beautiful churches I’ve ever seen. The €20 full-access ticket gets you inside the cathedral plus rooftop access (definitely take the elevator for €5 extra unless you love climbing stairs). Those 135 spires and thousands of statues are insane up close.
La Scala is legendary if you’re into opera, but even the museum and theater tour (€15) is worth it. The ornate boxes and that famous auditorium are stunning. Opera tickets range from €30 for nosebleeds to €500+ for premium seats – book way ahead for big names. The 2024/25 season runs through July 2025 with classics like Aida and La Traviata.
The Galleria Vittorio Emanuele II connects the Duomo to La Scala – it’s basically a gorgeous 19th-century shopping mall with Prada and Versace. Even if you’re not buying, the mosaic floors and glass dome are incredible. The bull mosaic tradition (spinning on its testicles for good luck) is touristy but fun.
Fashion Week happens twice a year (February and September), and the city goes absolutely crazy. The Quadrilatero della Moda is where you’ll find all the flagship stores, but honestly, window shopping is just as fun as buying. Brera and Navigli have better restaurants and nightlife – I love the aperitivo culture here.
Don’t sleep on Castello Sforzesco and its museums (€10). The courtyards are beautiful, and Michelangelo’s unfinished Pietà Rondanini is housed here. Milan’s surprisingly green with Parco Sempione right behind the castle.

5. Naples
Naples is chaotic and beautiful in the most authentic way. The Centro Storico UNESCO area has narrow streets bursting with life – colorful laundry hanging between buildings, street art, and baroque churches around every corner. Spaccanapoli literally splits the old city in half and offers incredible people-watching opportunities.
Mount Vesuvius looms over everything, creating this dramatic backdrop that’s both beautiful and ominous. Day trips (€40-60) to the crater give you incredible views over the Bay of Naples with the city sprawling below. Pompeii is mind-blowing – those preserved streets and frescoes frozen in time make for incredible photos, especially in early morning light before tour groups arrive.
The waterfront along Via Caracciolo offers stunning views across to Mount Vesuvius and Capri Island. Castel dell’Ovo on its little island creates perfect postcard shots, especially at sunset when the ancient stones glow. Posillipo Hill has the best panoramic views over the entire bay.
Quartieri Spagnoli (Spanish Quarters) might look sketchy but it’s full of vibrant street life and amazing murals. The narrow alleys and washing lines create authentic urban photography opportunities. Chiaia district has elegant 19th-century buildings and tree-lined streets that feel completely different from the historic center.
Capri day trip is absolutely worth it – that Blue Grotto and dramatic coastal cliffs are legendary. Sorrento and the Amalfi Coast are reachable too, offering some of the most beautiful coastal scenery in the world.

6. Verona
Verona feels like a fairy tale with its pink-hued medieval buildings and Roman ruins perfectly preserved. The Arena isn’t just for opera – this 2,000-year-old amphitheater is stunning any time of day, especially when golden hour light hits those ancient stones. Piazza Bra surrounding it creates the perfect wide-angle shot.
Juliet’s House and balcony are touristy but surprisingly photogenic. That ivy-covered courtyard with love notes covering the walls is actually quite romantic. The Casa di Giulietta architecture itself is beautiful Gothic style. Piazza delle Erbe with its medieval market stalls and frescoed buildings looks like a Renaissance painting come to life.
The Adige River curves around the city creating beautiful reflections of the medieval architecture. Ponte Pietra Roman bridge offers great views back toward the Arena and historic center. Castel San Pietro hilltop gives you the ultimate panoramic shot of the whole city with the river winding through it.
Castelvecchio fortress with its distinctive red-brick crenellated walls is gorgeous, especially from Scaliger Bridge. The Romeo and Juliet connection aside, Verona’s authentic medieval charm is incredible – those narrow streets and hidden piazzas are perfect for wandering with a camera.
Day trips to Lake Garda (30 minutes) offer stunning lakeside scenery. Sirmione peninsula jutting into the lake with its Scaliger Castle creates magical water views. The Valpolicella wine region has rolling hills covered in vineyards that are especially beautiful during harvest season.
- Read also: The Prettiest Cities in Europe in 2025

7. Siena
Siena is medieval perfection preserved in amber. Piazza del Campo with its unique shell shape and Torre del Mangia soaring above creates one of Europe’s most beautiful squares. The €10 tower climb gives you incredible views over those distinctive red rooftops and the Tuscan countryside rolling away to the horizon. Best light is late afternoon when everything glows golden.
The Duomo complex (€15) is a Gothic masterpiece – that black and white striped marble facade is absolutely stunning, especially when morning sun hits it. Inside, the marble floor mosaics (only uncovered certain times) and Piccolomini Library with Pinturicchio’s vibrant frescoes are incredible. The cathedral facade photograph beautifully from the steps.
Even without the Palio drama, wandering these medieval streets is magical. Via di Città curves through the heart of town with beautiful Gothic and Renaissance palazzos. The narrow alleys opening onto hidden piazzas create perfect urban exploration opportunities. Contrada neighborhoods each have their own character and symbols decorating the buildings.
Fortezza Medicea offers panoramic views over the city and countryside. The Basilica of San Domenico on its hill provides another great vantage point for sunset shots over the Campo. Those rolling Tuscan hills surrounding Siena are classic countryside – cypress trees lining roads and medieval hilltop towns dotting the landscape.
San Gimignano (45 minutes) makes an incredible day trip – those medieval towers rising from the hilltop create one of Tuscany’s most iconic skylines. Monteriggioni is a perfectly preserved walled village that looks like something from a medieval movie set.
- Read also: The Most Beautiful Destinations in Tuscany

FAQs 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.
What is the most beautiful city in Italy for art lovers?
For me, it’s Florence. I have spent hours wandering the Uffizi Gallery, standing in front of Botticelli’s Birth of Venus, and exploring smaller, lesser-known art spaces that most tourists skip. Florence blends Renaissance beauty with a walkable old town, making it perfect for travelers seeking art, history, and timeless charm.
Which Italian city is best for history buffs?
Rome is unbeatable. From the Colosseum to the Roman Forum and the Vatican, history is layered in every stone. Even just walking the streets feels like stepping back in time.
What is the most romantic city in Italy?
Venice wins this one for me. Yes, it can be busy, but venture away from St. Mark’s Square and you will find quiet canals, centuries-old bridges, and sunset gondola rides that feel like a scene from a movie.

Which Italian city is best for fashion and style?
Milan is Italy’s fashion capital, home to high-end boutiques, flagship designer stores, and trend-setting street style. I love exploring the Quadrilatero della Moda and finding hidden cafés between shops.
What is the best Italian city for foodies?
Naples. The pizza here is unlike anywhere else, and the street food scene is next-level. From fried seafood cones to sfogliatella pastries, it is a city made for eating.
Which Italian city feels like stepping into a Shakespeare play?
Verona. Its romantic streets and Juliet’s famous balcony draw visitors from all over the world. I found the best time to visit is early morning before tour groups arrive.

What is the most charming medieval city in Italy?
Siena captures medieval Italy at its best. Its fan-shaped Piazza del Campo and winding stone streets feel unchanged for centuries. Visiting during the Palio horse race is an unforgettable experience.
Which Italian city is best for first-time visitors?
If it’s your first trip to Italy, I often recommend Rome. It gives you a taste of everything—ancient ruins, world-class art, vibrant neighborhoods, and food that will set the bar high for the rest of your travels.
What Italian city offers the best mix of culture and scenery?
Florence is hard to beat for this combination. The city itself is a living museum, and just outside its center you have rolling Tuscan hills, vineyards, and hilltop towns that look like they belong in a painting.
Which Italian city has the most stunning piazzas?
Siena’s Piazza del Campo is my personal favorite. It is one of the most beautiful public squares in Europe, and watching life unfold here from a café table is an experience you will not forget.

Need help planning your trip? Check out these helpful links:
- ✈️ Find cheap flights – I save $10k per year on flights thanks to this tool
- 🏨 Book accommodations – My favorite platform for boutique hotels and budget stays
- 🚗 Compare rental car prices – Great rates from trusted companies
- 🎟️ Discover affordable tours and day trips – Skip the line and explore more