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12+ Prettiest Cities in Italy | Best Places to Visit in Italy

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Looking for the prettiest cities in Italy? Keep reading!

Italy is one of the most charming and magical countries on Earth. The whole country is full of beautiful cities, towns, and villages, and choosing the prettiest cities in Italy is indeed a challenge.

With so much history, unique architecture, and breathtaking landscapes, it is no wonder why Italy is one of the most sought-after travel destinations in Europe and a personal favorite of mine! In fact I have visited Italy over 10x in the last 5 years exploring all the different towns and cities to find the best of the best.

Now, it’s time for you to see the top 12 prettiest cities in Italy and make your wanderlust for this stunning country even greater.

12+ Prettiest Cities in Italy

Short on time? Here are the 5 Prettiest Cities in Italy
🇮🇹 Matera, Italy
🇮🇹 Polignano a Mare, Italy
🇮🇹 Venice, Italy
🇮🇹 Positano, Italy
🇮🇹 Alberobello, Italy

Matera, Italy

Matera is easily one of Italy’s prettiest cities and is even one of the most beautiful cities in the world. Located just beyond the magical region of Puglia this inland gem is one of my favorite places in Italy that absolutely blew me away.

The most distinctive feature of Matera is its ancient cave dwellings, known as Sassi. These UNESCO World Heritage-listed caves have been carved into the limestone over millennia, creating a maze of narrow streets, hidden courtyards, and panoramic viewpoints that offer stunning views.

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Beyond its beauty, a visit to Matera is like stepping back in time. It is a place of lengthy history and tradition that only adds to the magic of it.

💡 IN FACT: Matera is the oldest continuously lived settlement in the world

Matera is a must-visit to immerse yourself in one of the prettiest cities in Italy where timeless beauty blends with a rich history.

Where to stay in Matera

💡 Riscatto 1514
💡 Hotel La Casa Di Lucio
💡 Sextantio Le Grotte Della Civita

Polignano a Mare, Italy

Polignano a Mare, situated on the stunning coastline of Puglia in southern Italy, is one of the country’s most picturesque cities. Located atop jagged limestone cliffs that drop into the clear blue waters of the Adriatic Sea, Polignano a Mare is an absolutely stunning destination.

Its historic center is characterized by whitewashed buildings complete with flowers, exuding an irresistible Mediterranean charm.

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What makes Polignano a Mare truly special is its blend of natural beauty, cultural heritage, and laid-back ambiance. A visit here is the perfect place to experience the magic of Italy’s Adriatic coast in a truly unforgettable setting.

Where to Stay in Polignano a Mare

🌞 Dimora Anderì
🌞 POSEA – Polignano Sea Suites

Venice, Italy

Venice is one of those classic Italian cities that everyone needs to visit at least once in their life. Characterized by its hundreds of canals, pastel-colored buildings, authentic gondolas, and ornate churches, Venice is a romantic and historic city with architecture that will awe you.

Venice does not have any cars or buses, which makes it all the more beautiful. The main mode of transportation is by water along the hundreds of beautiful canals.

In fact, the best way to see the city is with a Gondola which will take you down the little side canals and along the stunning Grand Canal.

Visit Venice at any time of the year. All seasons offer something unique and lovely to see and all have their own specialties. This is also one of the best places to visit on an Italy road trip.

Read More: How to spend one day in Venice, Italy

Where to stay in Venice

🍷 Hotel Metropole Venezia
🍷 The St. Regis Venice
🍷 Carnival Palace

San Gimignano

San Gimignano is a stunning medieval hilltop town in the heart of Tuscany. Celebrated for its remarkable skyline with ancient towers, earning it the nickname “the Manhattan of the Middle Ages.”

Located atop a picturesque hill overlooking the rolling vineyards and olive groves of the Tuscan countryside, San Gimignano captivates with its timeless beauty and rich history.

It’s well-preserved medieval atmosphere and its ability to transport you back in time is just one of the reasons this is considered one of the prettiest cities in Italy.

Where to Stay in San Gimignano

🇮🇹 Hotel Bel Soggiorno
🇮🇹 Hotel & Restaurant Casolare Le Terre Rosse

Saturnia, Italy

Blue hued waterfalls in Saturnia

Saturnia is a small ancient town located in Tuscany, Italy. The town itself is old and is full of history and well worth exploring, but the main draw to the city is the thermal hot springs. The hot springs are called Cascate di Mulino and are a unique and stunning place to visit in Italy.

Beyond its obvious beauty, the water in the hot springs is said to have healing and therapeutic properties. Many tourists and locals flock to them to help with skin conditions and heal their bodies in the cascading waterfalls and pools.

People swimming in the hot springs

The water stays at 37°C year-round and is open 24/7 365 days a year. More so, as of now, these pools are free to enter, and since they are not very well known they are not as busy as other thermal baths.

However, in the on-season, you will find quite a few people soaking up the water’s beneficial minerals.

Where to Stay in Saturnia

🌊 Saturnia Tuscany Hotel
🌊 Terme di Saturnia Natural Spa & Golf Resort

Positano, Italy

Colourful houses built vertically up the mountain in Positano

Positano is a dreamy Italian village that will enchant you from start to finish. From the houses built into the rugged mountains to the pastel-colored homes, to the colorful beach and beyond, Positano is a travel destination like no other.

In addition to the beautiful architecture, Positano is lined by a beautiful beach with vivid blue waters. From the beach, you can look back and see the whole city built vertically and the huge towering mountains in the distance. It truly is something from a fairytale.

Year-round Positano boasts stunning views and lovely sites to see and visiting any month of the year is suitable. However, the summer months can get extremely crowded, so if you value fewer crowds while you travel the offseason is a better time to visit.

Read More: 20 Things to do in Positano, Italy

Where to stay in Positano

☀️ Il San Pietro di Positano
☀️ Le Sirenuse

Florence, Italy

Florence is often regarded as one of the prettiest cities in Italy due to its unique architecture, cobblestone streets, and ornate detailing.

The city is well known for its buildings such as the Cathedral of Santa Maria del Fiore and Palazzo Vecchio which you could easily stare at for hours.

These buildings are impressive not only from the outside by also from the inside. The Duomo holds artwork from renowned artists such as Michael Angelo, Leonardo da Vinci, Raphael, Titian, and much more!

Be prepared to feast your eyes while visiting Florence and take in all the beauty that radiates from the architecture.

Beyond the famous buildings, Florence has a ton of other beautiful little streets and squares waiting to be explored. It is a city that keeps on giving, and you will not be disappointed. It is also the perfect stop during a Northern Italy road trip!

Where to Stay in Florence

⭐️ Borgo Signature Rooms
⭐️ Portrait Firenze

Alberobello, Italy

Alberobello is located in the heart of Puglia and is famous for its unique Trulli houses! These unique whitewashed buildings with their conical roofs create a fairytale-like atmosphere that is incredibly different from anywhere else in the world.

The historic center of Alberobello, a UNESCO World Heritage site, is a maze of winding streets and alleys lined with hundreds of Trulli, each with traditional symbols and intricate stone carvings.

What sets Alberobello apart is its timeless charm and sense of wonder. Whether admiring the Trulli, sampling local food or simply soaking up the atmosphere in the town’s lively piazzas, Alberobello promises an unforgettable journey through the magical landscapes of Apulia.

Where to Stay in Alberobello

🍝 Trullidea
🍝Trulli Antichi Mestieri

Bellagio, Italy

Bellagio is a stunning town located in Lake Como. It is famous for its breathtaking beauty and old-world charm, making it one of the prettiest cities in Italy.

Read More: 10 Best Things to do in Bellagio, Italy

I love Bellagio for its waterfront promenade, lined with colorful pastel-hued buildings, local cafes, and boutique shops. This paired with the town’s historic cobblestone streets and lush garden villas make it utterly AMAZING!

Where to Stay in Bellagio

➡️ Hotel Florence
➡️ La Terrazza Cavour

Sorrento, Italy

Tall pink houses built into the cliffs in Sorrento

Sorrento is a hidden gem of the Amalfi Coast that offers more than meets the eye. This beautiful city sits high along the cliffs and dangles dangerously close to the edges.

The city is full of charm and once you get up the steep cliffs you are welcomed to colorful buildings, cobblestone streets and charming restaurants. From the city, you are able to overlook the whole Bay of Naples and admire the water and beaches below.

Sorrento is also home to some unique beaches made on platforms instead of on sandy beaches. The waters surrounding them are turquoise blue and offer a vibrant beach day experience.

Where to Stay in Sorrento

🍋 Hotel Rivoli Sorrento
🍋 Grand Hotel Royal

Rome, Italy

Rome is a historian’s dream travel destination! This city is full of excitement, ancient history, and beauty. Rome’s deep-rooted history is evident in the Forum Roman and the Colosseum, which is the largest amphitheater that has ever been built and one of the New Seven Wonders of the World.

In addition to Rome’s interesting and profound history, it is also one of the prettiest cities in Italy. The streets are all full of color and around every corner, you will find a new beautiful square and stunning building to admire.

Read More: A Guide to Rome in January

Where to Stay in Rome

➡️ Baglioni Hotel Regina
➡️ The St. Regis Rome

Cinque Terre, Italy

Colourful houses of Cinque Terre

Cinque Terre is a colorful and vibrant seaside village located along the Italian Riveria coastline. Photos of this stunning location have made waves on social media with everyone drooling over the bright colored buildings and blue water surroundings.

There are actually a few different villages within the Cinque Terre strip all just as beautiful. The houses here are built onto the steep rugged cliffs resulting in a very unique city view. The best way to see the city is by going on one of the many hikes that take you along the coast.

Visiting Cinque Terre in the summer can become quite crowded as tourism here has exploded in recent years. However, this does not take away from the fact that it is one of the prettiest cities in Italy.

Where to Stay in Cinque Terre

🌊 La Linea D’Acqua

Siena, Italy

Siena is a beautiful Italian city that is full of unique medieval architecture and authentic Italian streets. The buildings here look quite different from the pastel-colored, vibrant ones in most Italian cities, which is a welcome difference when traveling around Italy.

Siena has even earned itself a UNESCO title as the embodiment of a medieval city.

More so, the city is built on three hills and its high elevation offers some very unique perspectives and vantage points. Everything combined shows a different side to Italy that most cities do not have.

Where to Stay in Siena

🍕 Grand Hotel Continental Siena
🍕 Hotel Certosa Di Maggiano

Stintino, Sardinia

Stintino, a charming coastal town on the northwest tip of Sardinia, is renowned for its beautiful beaches, clear waters, and rugged beauty. The town’s highlight is La Pelosa Beach, known for its powdery white sands, crystal-clear waters, and iconic Spanish watchtower. This beach is as postcard-perfect as it gets!

Beyond its stunning beaches, Stintino offers a wealth of outdoor activities such as hikes, boat tours, snorkeling and more!

What makes Stintino truly special is its unspoiled natural beauty, secluded beaches, and authentic charm, offering visitors a tranquil retreat and a glimpse into the idyllic lifestyle of coastal Sardinia.

Where to Stay in Stintino

🌞 Park Hotel Asinara

Italy is one of the magical countries that you can visit time and time again and there is always something new and beautiful to discover. This list only holds 12 of the prettiest cities in Italy, but I know there are about 50 more that could be added.

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