21 Prettiest Cities in Italy for Your Bucket List

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Italy often frequents the very top of most peoples’ bucket lists and it’s no wonder why. From stunning landscapes to the jaw-dropping coastlines to the mouthwatering food, Italy has it all. It’s one of those countries that you dream about returning to immediately after you leave. I teamed up with some travel bloggers who love this charming country just as much as I do to uncover some of the prettiest cities in Italy. 

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21 Prettiest Cities in Italy for Your Bucket List

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The following cities will give you a glimpse of why Italy is such a popular destination and why tourists can’t get enough of it.  You won’t be left disappointed no matter where you choose to visit. 

 

1. Siracusa

By Marta of Mama Loves Italy

Siracusa is a beautiful town on the eastern coast of Sicily, famous for a historical city center and an important archaeological park dating back to Greek and Roman times.

The center of Siracusa is called Ortygia and develops over a small island. It’s connected to the rest of the city by pedestrian bridges and with a beautiful seaside promenade.

Ortygia is a delight of meandering alleys and it is home to many of the most important landmarks in the city, namely, the cream-colored, striking Duomo, the ancient Arethusa Fountain, already known to the Greek founders of the city and the Temple of Apollo, one of the most ancient Doric temples in Sicily.

Ortygia is also the most pleasant part of the city for a meal, thanks to its many local restaurants and bakeries. 

Outside of the center, the Neapolis, Siracusa’s archaeological park, is also not to be missed. Here, you find a beautiful ancient Greek theater and the daunting Latomie, ancient quarries excavated in the flanks of an impressive mountain, now accessible via an easy path. 

Both Ortygia and the park can be visited in one day. You can learn how to best plan your time in Siracusa. 

• Recommended Places to Stay in Siracusa

2. Perugia

By Michael of The World Was Here First

One of the prettiest cities in Italy is the beautiful student city of Perugia located in the Umbria region of central Italy. Often overlooked by travelers on a short trip through the country, its location almost exactly halfway between Rome and Florence makes it a great option for people looking to get off the beaten path in Italy.

There are several interesting sites to explore in Perugia that can occupy travelers for a day or two. One of the best things to do is walk through the “Underground Perugia” which is an entire network of underground streets that are the remains of a 16th-century fortress.

Visitors to Perugia should also stop by Piazza IV Novembre, one of the central meeting points of the city, as well as enjoying the spectacular views at Giardini Carducci.

Perugia also makes for a great base to explore the Umbria region and visitors to the city can take a day trip to the town of Assisi, a famous pilgrimage site. Alternatively, head to one of the nearby local vineyards to sample some delicious wines.

• Recommended Places to Stay in Perugia

3. Pompeii 

By Pamela of The Directionally Challenged Traveler 

When you think of the prettiest cities in Italy, you tend to think of the beautiful cathedrals of Rome or the winding canals of Venice, or overlooking the Ponte Vecchio in Florence. One city that is often overlooked is the ancient city of Pompeii. 

In 79 AD, the looming Mount Vesuvius erupted. The force was so powerful that the top of the mountain blew off, sending ash and dust miles into the sky and eventually thick ash and superheated rock into the town.

About 2,000 years later, archaeologists found the town and were able to pour plaster into the body-shaped spaces in hardened ash for a glimpse into life in Pompeii before the eruption.

Visiting Pompeii is a unique experience and one that shouldn’t be missed when in Italy. While some tours only last a few hours, you can easily spend a day walking through the city.

Explore the large amphitheater and the houses to see how the people of Pompeii lived. There are some houses that are so well preserved the wall art is still visible. You can spot wall art at the House of the Vetti and the House of the Tragic Poet.

Italy is a great country to wander through history and Pompeii is a city that allows you to do so on an intimate level.

• Recommended Places to Stay in Pompeii

4. Milan

By Disha of Disha Discovers

Milan is a city that most tourists look over. But, you shouldn’t dare skip a visit to this elegant city. If you’re after world-class shopping, delicious food, stunning art, and more, you’re guaranteed to have a great time and fall in love with this city.

Milan is quieter than other Italian cities and you’ll be able to roam the streets without bumping shoulders with other tourists. Milan is home to some of the biggest brands in the fashion industry including Prada, Versace, Dolce and Gabbana, and more. Milan is also the perfect base to explore Northern Italy and Switzerland.

When in Milan, you have to explore Piazza del Duomo. Here, you’ll find the truly magnificent Milan Cathedral. You also have to visit Grand Galleria Vittorio Emanuele II. This is a beautiful shopping mall that looks like a theater or an opera house. In fact, it’s one of the oldest shopping malls in the world. If you have time, watch a show at La Scala Opera. 

• Recommended Places to Stay in Milan

5. Matera

By Claudia of My Adventures Across the World

A UNESCO World Heritage Site since 1993, Matera will capture you with its unique, breathtaking beauty. Located in Basilicata, southern Italy, its reputation was that of “shame of Italy” until the 1950s, when the Sassi di Matera – the famous cave dwellings where people have lived since the Paleolithic – were emptied of their inhabitants and completely restored.

Since then, people have moved back and the city turned into a real gem, with a magic atmosphere – so much so that it became a favorite movie set for many films, including internationally acclaimed The Passion of the Christ by Mel Gibson.

There are many things to do in Matera, and you can easily spend a couple of days wandering around without ever getting tired. The main attractions are all in the Sassi – Sasso Caveoso and Sasso Barisano, which correspond to the historic center and are divided by Civita hill.

Scattered in the Sassi you will find museums, rock-hewn churches (the most interesting one to visit is the Church of Santa Maria de Idris), the cathedral, a couple of historic homes where you can get an idea of what life used to be like in the Sassi until the 1950s, and a plethora of viewpoints.

Yet, the best views of Matera are from Parco della Murgia, where you will find more rock-hewn churches. Make sure to go there in the afternoon for a chance of admiring an unforgettable sunset.

• Recommended Places to Stay in Matera

6. Cinque Terre

By Jamie of Fly By the Seat of Our Pants 

Cinque Terre isn’t just a great city in Italy. It’s actually five quaint, coastal towns you’ll fall in love with.

No cars are allowed into Cinque Terre so you’ll have to ride the train into the heart of each town. For more adventure, hike along the coast from city to city. The only way to move through the city is on foot. So, be prepared for vertical climbs and descents as the towns are built right up the coastal hills.

You will love the colorful buildings, the narrow passageways, and the gorgeous views throughout the Cinque Terre Region. Start at the furthest city along the train path and make your way back. Wander through shops and homes up and down the coast.

Be sure to lounge on the beach and climb the giant boulder on the coast of Monterossa. Enjoy the bay and the church in Vernazza. Hike through vineyards along the Mediterranean Sea to Corniglia. Lick gelato while enjoying the architecture and landscape in the fishing village of Manarola. Admire the solid castle walls in Riomaggiore.

Cinque Terre will quickly be one of the prettiest cities in Italy that you visit!

• Recommended Places to Stay in Cinque Terre

7. Sorrento

By Chrysoula of Travel Passionate

The stunning city of Sorrento, overlooking the Bay of Naples, is the gateway to the gorgeous Amalfi Coast. Even if you don’t have time to take a full road trip around the area, the city itself is well worth a visit.

Home to dramatic hikes, pristine piazzas, meandering shopping streets filled with boutiques, and a wonderful collection of museums, Sorrento is a great place to kick back and relax while still having plenty to do if you wish.

As with every trip to Italy’s southern coast, it’s important to mention the impressive coastal views, delicious cuisine, and laid-back lifestyle that makes this city such an excellent destination for a getaway. 

Take a stroll among the boats in the pastel-hued Marina Grande, try freshly pressed olive oil at a local grove farm, sip limoncello as the sun goes down, and dine on traditional dishes in one of the many Italian trattorias located on the squares and seafront of this city.

If you are lucky enough to have a few more days to explore, why not use Sorrento as a base for discovering the ancient city of Pompeii, the island of Capri, or some of the smaller towns located along the Amalfi Coast?

• Recommended Places to Stay in Sorrento

8. Bologna

By Kate of Our Escape Clause

Not only is Bologna one of the prettiest cities in Italy, but it’s also widely considered to be one of the best food cities in all of Italy. Therefore, in the entire world, Bologna, Italy is a captivating Italian city and a must-visit destination for food lovers.

As the capital of Emilia-Romagna, Bologna has been an intellectual and culinary marvel for centuries, which you can see reflected in the city’s three nicknames: la grassa (the fat, for the food), la rossa (the red, for its beautiful architecture), and la dotta (the learned, for its impressive university).

Some of the best things to do in Bologna include climbing to the top of the (leaning) Asinelli Tower, visiting the Piazza Maggiore, seeking out the city’s hidden canals, and enjoying the view from San Petronino’s Terrace.

Plus, of course, there’s the food: touring Bologna effectively means eating your heart out, and given how delicious every bite is, you won’t complain!

Emilia-Romagna is the original source of tagliatelle al ragu (the “real” version of what the rest of the world calls spaghetti bolognese), mortadella (also known as bologna outside of this region), balsamic vinegar, and parmigiano-reggiano.

Each of these dishes is infinitely better than any of the copycats you’ve tasted outside of Emilia-Romagna, and all deserve to be enjoyed during a trip to Bologna.

• Recommended Places to Stay in Bologna

9. Cagliari 

By Claudia of Strictly Sardinia

Cagliari is one of the most underrated and prettiest cities in Italy. Pleasant year-round, thanks to good weather, Cagliari is at its best during the late spring and summer months when you can enjoy all its beautiful sights as well as its many urban beaches.

Poetto, the local’s favorite, is a long sandy beach scattered with nice kiosks, restaurants, great sand, and clear waters. Right behind it, Molentargius Nature Reserve is a great place for bird-watching. Go at sunset to admire pink flamingos as they feed in the calm waters of the lagoon. For beautiful views of the coast, head to Calamosca beach, where you’ll find an easy hiking trail that leads all the way to Sella del Diavolo, one of the most famous landmarks in town.

For more of a cultural or city scene, head to the historic center of Cagliari. The best museum is the Museum of Archeology, located in the Castello district. Walk through Porta Cristina and inside Castello you will find the two watchtowers – San Pancrazio and dell’Elefante, at the other end of the district; as well as the beautiful Cattedrale di Santa Maria.

The Roman Amphitheater and Punic Necropolis are the most important (though not the only) archeological sites in town. Castello, La Marina, Stampace, and Villanova are the four historic districts and a maze of colorful alleys and sights. There you will find many cozy coffee shops, restaurants, and wine bars.

For the best sunset in town, head back to Castello and walk to Via Santa Croce. The views over Stampace and all the way to Sette Fratelli Mountains are stunning.

The best nightlife in town is in the Stampace and La Marina districts. That’s where you will find the best selection of pizzerie, restaurants, and bars.

• Recommended Places to Stay in Cagliari

10. Rome

By Disha of Disha Discovers

Rome is hands down one of the most popular and prettiest cities in Italy to visit. You honestly don’t need much convincing to visit the Eternal City. It’s home to several historical sites, archaeological sites, paintings, museums, galleries, and more. You definitely won’t run out of things to do here!

Rome is known for its history, architecture, food, wine, fashion, street art, gelato, and more. This city honestly has it all. Every street has something new for you to explore and it’s rare to find another city in the world with so much history. 

Some must-do things in Rome include hanging out at the Spanish Steps, exploring the infamous Colosseum, taking a selfie in front of the Trevi Fountain, learning about history at the Pantheon, studying Christianity and visiting another country at Vatican City, wandering through the Sistine Chapel, and visiting the Roman Forum. These are just a handful of the many things you can do in Rome.

After a long day of sightseeing, you’ll definitely want to indulge in some delicious Italian food. Ordering a pizza at Dar Poeta is a must! In case you’re wondering, you should get your own pizza and don’t attempt to share one with your friends. Rome is brimming with amazing restaurants. Your best bet is to use TripAdvisor and see what highly rated restaurants are in your area.  

• Recommended Places to Stay in Rome

11. Siena

By Or of My Path in the World

Whether you’re taking a road trip through Italy’s Tuscany region or planning an Italian weekend getaway, Siena is one of the best and prettiest cities in Italy. With a beautiful landmark-packed historic center that is a UNESCO World Heritage Site, impressive and fascinating museums, and an exquisite culinary scene, it is one of the best cities in Italy for culture, history, and architecture lovers.

One of the top places to visit in Siena is the Duomo, a medieval church dating back to the early 13th century. It’s incredibly detailed and impressive both on the outside and inside, as it was created by Italy’s finest architects and artists. It also houses the beautiful Piccolomini Library.

Next, head to Piazza del Campo, one of Europe’s most amazing medieval squares. It’s also where you’ll find the 13th-century Palazzo Pubblico (town hall) and the 14th-century Torre del Mangia, the second-tallest non-religious tower in Italy.

Other interesting things to do in Siena include wandering the streets of the historic center and visiting the old synagogue, botanical garden, and the Pinacoteca Nazionale art museum.

• Recommended Places to Stay in Siena

12. Naples

By Pauline of Beeloved City

If you love history, Naples is the perfect destination for you!

Located in Southern Italy, Naples is known for its Greek and Roman heritage and also for its food. It is the birthplace of Italian pizza and espresso. Foodies are in for a treat! Make sure to try the local delicacies: the pizza fritta and rum baba.

This bustling city is full of hidden gems and beautiful landmarks. One of the best ways to explore it is by taking a walking tour. The local guide will tell you everything you need to know about the Royal Palace, the Greek, and Roman history, and will take you to Naples’ most famous street: Spaccanapoli.

If you can, make sure to take the funicular and visit Castel Sant’Elmo. Perched on a hill behind the Spanish quarters, the castle is an excellent viewpoint. The views over the city and Mount Vesuvius are absolutely stunning.

Finally, don’t forget to explore the surroundings. Going on a day trip from Naples to Pompeii, Herculaneum, Capri Island, or the Amalfi Coast is an amazing experience.

If you love hiking, you can also go to Mount Vesuvius. Hiking on an active volcano is an experience of a lifetime.

• Recommended Places to Stay in Naples

13. Verona

By Nichola of Family Hotel Expert

Verona is one of the most underrated destinations and prettiest cities in Italy. Visitors will often go sailing past on the way to Venice but they’re overlooking a city that is perfect for a family holiday in Italy or a city break for couples or individuals.

There is so much to see here from the Arena in the center (which is older than the Colosseum in Rome) to the beautiful Lamberti Tower.

The setting for Shakespeare’s Romeo and Juliet, there are nods to this fictional tale across Verona. Stand on Juliet’s balcony or stop at one of the many bakeries to eat delicious biscuits named after these doomed lovers.

This is a city that doesn’t have the crowds of Venice but has the sights, the history, and all the wonderful architecture. One of the best ways to see it is to take a bicycle tour and lose yourself in all the beautiful lanes crisscrossing the center. However long you come for you’ll wish you had longer.

• Recommended Places to Stay in Verona

14. Alberobello

By Alessia & Toti of Italian Trip Abroad

You might don’t know yet, but Alberobello is recognized as a World Heritage Site by Unesco for its Trulli. This white town is one of the prettiest cities in Italy. Located in Southern Italy, in the region of Puglia, Alberobello is the most recognizable place in this part of the country.

The cone-shaped houses are famous all over the world and are on the bucket list of places to visit for every curious traveler. Alberobello is famous for these weird houses, whitewashed with a stone cone as the roof.

The history behind these quirky houses is funny. In ancient times, the taxes on the land were paid for the house built on. The old Lord of the Valley tried to pay fewer taxes to the King and was ordered by the locals to build houses that could be demolished and raised quickly.

In the case of Royal Inspection, the Valley was empty. After a while, the peasants tried to demolish and build their homes. They complained to the king who then took all the land away from the Lord and then maintained those houses.

Today, the Trulli houses are a recognizable mark of the past of Alberobello. They’re spread all over the valley and have become elegant and glamorous accommodation spots and restaurants surrounded by olive trees and vineyards.

Visit the beautiful Trulli of Alberobello and discover how local life is. You can also book a room and stay in the city for a few days. The vibes, the local flavors, and the tasty food will give you memories that will last a lifetime. Visit the Trullo Church and the rooftop in the city center to enjoy the view from the top.

• Recommended Places to Stay in Alberobello

15. Fiesole

By Mel of TravelingMel

Fiesole is a little village perched on a hillside overlooking Florence. While it’s just a short bus ride from Florence these days, it used to be a getaway in the country for wealthy and royal people from the city.

Today, many tourists like a day hike near Florence in Fiesole as their own escape from the city. The Stonemasons and Leonardo Trails wind through the colorful, narrow streets of Fiesole and the cypress and olive groves in the Italian countryside. Along the way, panoramic views of Florence spread out in front of walkers. The trail passes the hillside where Leonardo da Vinci did his human-powered flying experiments.

After walking the trail, stop by the Monastery of San Francesco to visit the chapel and visitor center. The Etruscan-Roman Archaeological Area has an intact Roman amphitheater and Byzantine art. On some weekend days, you can stroll through the market in Piazzo Mino.

• Recommended Places to Stay in Fiesole

16. Venice

By Disha of Disha Discovers

Tourists usually have a love/hate relationship with Venice. The crowds can get overwhelming at times. But, hear me out – Venice is definitely worth a visit even if it’s only for a day trip. It’s one of the most visited travel destinations in the world and for good reason!

Known as the “Floating City,” Venice has been a UNESCO World Heritage Site since 1987 and it’s built on 118 islands on a lagoon. It’s known for its canals, bridges, palaces, and more. It has no roads accessible by car so the main means of transport is with boats and ferries.

Venice is oozing with Venetian Gothic architecture that originated in the 14th century. You can especially notice this style at Doge’s Palace. Venice is also a seafood lover’s heaven and you can find incredible restaurants that serve it anywhere in the city. 

One of the best things to do in Venice is to just get lost and wander around the streets. You can walk around the city in a few hours since it’s small. Take a break and enjoy some coffee at one of the many cafes as well. Then, head over to St. Mark’s Square. Don’t forget to check out the famous Rialto Bridge, Venice’s most popular bridge. Lastly, your trip to Venice won’t be complete without a gondola ride through the canals. 

Read my post about 40 things to know before visiting Venice to help you plan your trip!

• Recommended Places to Stay in Venice

17. Lecce

By Nadine of Le Long Weekend

Located at the heart of Salento, Lecce is one of the most beautiful and historical cities in Puglia – the region that encompasses the heel of Italy’s boot. Bursting with baroque architecture and impressive cultural attractions, it’s somehow remained a relatively undiscovered gem.

Wandering through the city, you’re almost transported to another time, the city’s façades wearing their stories as art. Yet the upmarket boutiques and eateries tell another story, one of a city with a vibrant and upbeat atmosphere, where the locals love to gather on the cafe terraces and talk into the small hours.

The most incredible sights can be found within the historical center, where you’ll discover a Roman amphitheater, another impressive Roman theatre, stunning baroque churches, and the 12th-Century castle of Lecce.

Due to its central position, Lecce makes a brilliant place to stay in Puglia from which you can reach both coasts, and many other brilliant towns and villages easily. 

• Recommended Places to Stay in Lecce

18. Lucca

By Linn of Brainy Backpackers

Lucca might just be one of the most underrated and prettiest cities in Italy with an intriguing history and stunning medieval architecture. Most visitors go on a Florence to Lucca day trip, but the town surely deserves more time than that.

Spend a couple of nights inside the city walls, climb the clock tower for spectacular views of the city and take a stroll on top of the city walls.

Lucca Cathedral is a unique structure dedicated to Saint Martin. Each one of the columns on the facade features different styles, and it’s said that they’re created by different artists during a competition.

Other churches worth visiting are the Basilica of San Fernando and San Michele Foro, which might just be the most photographed building in Lucca.

The Piazza del Anfiteatro is a must for lunch if not just strolling around the square knowing that under the ground are the rests of the ancient amphitheater. The houses that surround the square are built in a ring, marking the size of the original structure and they are built around some of the original arches.

• Recommended Places to Stay in Lucca

19. Florence

By Krisztina of She Wanders Abroad

Often referred to as the birthplace of the Renaissance, Florence is one of the prettiest cities in Italy you absolutely can’t miss. The capital of Tuscany offers many interesting museums for art and culture lovers, such as the Uffizi Gallery or the Galleria dell’Accademia where you can see the famous David statue.

The Cathedral of Santa Maria del Fiore is probably the most famous landmark of the city and it’s a must-visit place on every Florence itinerary. The cathedral looks breathtaking both outside and inside, so it’s definitely worth checking out. You can visit the cathedral complex with a single ticket but for going up to the dome you will need to book a timeslot in advance.

Crossing the Arno River on Ponte Vecchio is another must thing to do in Florence. The bridge is pretty unique because it’s a closed-spandrel segmental arch bridge that is home to many shops selling artworks, jewelry, and souvenirs. If you like shopping, it’s worth visiting the famous outdoor leather market called Mercato San Lorenzo in the heart of the city.

There is no better way to end your day in Florence than seeing the sunset from Piazzale Michelangelo, from where you can get an incredible panoramic view of the city.

• Recommended Places to Stay in Florence

20. Positano

By Heleen of The Global Wizards

The beautiful and unique town of Positano is situated along the world-famous Amalfi Coast. Its colorful houses climb the steep cliffs, making this place most known for its breathtaking views, narrow streets, and stunning beaches.

Getting to Positano is an adventure in itself. The winding, busy and small road up to Amalfi passes the town. You could reach it by driving yourself on a scooter or motorbike. However, if you want to go by car you better decide to take a bus from Sorrento or Salerno.

A fantastic alternative is taking the boat, which means you will be treated to the most famous view of Positano when you enter its harbor.

Take your time to explore this unique place. Climb the many steps, shop in its beautiful stores, stay in one of the rustic Italian hotels admiring the views, or spend a day on the beach as the real Italians do.

You could choose to go to the main beach, but if you take a little walk, you’ll discover many secluded beaches around town. End your day with a drink during sunset and discover its vibrant nightlife. You won’t be bored in Positano.

• Recommended Places to Stay in Positano

21. Pisa

By Lyndsay of The Purposely Lost

Although most people only go for a few hours, Pisa is one of the best and prettiest cities in Italy. Although most people only visit the Leaning Tower, there is so much more to do in this historic city.

Originally constructed as a bell tower to the adjacent cathedral, the Leaning Tower of Pisa began to tilt when the second floor was built in the 1300s. But once you’re visiting the Tower, make it a point to discover the rest of Piazza dei Miracoli, including the Cathedral, the Baptistry, and the Cemetery.

Also, take a stroll along the Arno River, which divides the city into two sections. There are many restaurants and shops all along the river, and you might get lost exploring various stores for hours. You can easily spend more than one day in Pisa.

Another favorite section of the city is Marina di Pisa. Just 20 minutes west of the center of the city, you’ll be at the beautiful coastline. The sandy beaches are lovely, and you could rent a lounge chair or lay a towel right beside the water, or enjoy any of the restaurants and nightclubs along the coast.

• Recommended Places to Stay in Pisa

Which one of these prettiest cities in Italy are you most excited to visit? Let us know in the comments below! 

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