Ah Italy. I always say that it is impossible to have a bad time in Italy. Not only are there so many beautiful cities in Italy, but you can also almost guarantee that they will all offer fantastic food, wine, and coffee.
As a travel blogger I am lucky enough to travel more frequently than the average person. I have actually now lost track of how many times I have visited Italy – it must be at least 20. And I don’t plan on stopping there – Italy will be one of my favourite travel destinations for the rest of my life.
1. Syracuse
I loved Syracuse – it was a highlight of Sicily where to stay. It is such a cute and atmospheric city. The old town of Ortygia is the place to stay, eat and wander. It is at its most magic as the sunsets. Ortygia is the perfect Italian old town. It is full of little streets that are perfect for wandering. The best time to go is early evening – kick-off about 30 minutes before the sunset.
2. Montepulciano
Montepulciano is quite frankly heaven for wine lovers. This stunning hilltop Tuscan town is ridiculously beautiful and it is just filled with wine. Wineries, red wine, white wine, wine cellars, oak casks, wine shops, wine bars – it really is just wine-tastic! There are so many wineries in Montepulciano.
3. Ostuni
This gorgeous white city is set on a hilltop only 8km from the sea and one of the key Puglia destinations. It was raining when I visited but still very cute. It is not easy to find your way around the narrow streets – apparently, the town was built without a plan which makes perfect sense after you have visited.
4. Rome
Yes it is a little dull to have Rome in a list of the most beautiful cities in Italy but the reality is that Rome is an incredibly beautiful city. Italy’s capital sits on the Tiber river and often has more tourist attractions in two streets than entire cities.
It is, of course, mandatory to visit the Colosseum, the Vatican, Trevi Fountain, the Pantheon, etc but for me, the best of Rome is just walking through its beautiful streets and being in Rome.
5. Ravenna
Lovely Ravenna was the capital of the Western Roman Empire from 402 until 476. As such it has some stunning architecture which has been very well preserved and is home to several UNESCO sites.
6. Rimini
Rimini has long been famous for its long stretches of golden sands and location on the Adriatic Sea. However, the big surprise for me in Rimini was its absolutely charming old town.
7. Venice
A bit like Rome, it isn’t possible to speak about beautiful cities in Italy without mentioning Venice. Sure it is usually full of tourists but it doesn’t stop it being a special moment when you first visit this famous city.
8. Parma
One of the largest cities in Italy’s breadbasket region of Emilia Romagna, Parma is best known for its famous cheese and prosciutto. Personally, I feel that a Parmesan tasting is mandatory for any visit to Parma.
9. San Marino
San Marino is the oldest republic in the world and no one has ever taken it over. This small country of just 61 square kilometers sits atop a hill and overlooks the Italian countryside.
10. Alberobello
There are so many things to do in Puglia – and lovely UNESCO World Heritage Site Alberobello – which is also very fun to say – is one of Puglia’s Trulli towns. A Trulli is basically a white stone cottage with a cone-shaped roof. They are a cross between something from early Star Wars and the kind of place you would expect to find in a desert in the Middle East.
11. Lucca
Lovely Lucca is the quintessentially beautiful Tuscan town. This walled city is filled with atmospheric back streets and cobblestones. It is known as the city of 100 churches so there are loads to visit if that’s your thing.
12. Taormina
Taormina is a ridiculously gorgeous town in Sicily. The town itself is pedestrianized and filled with cute backstreets and lovely architecture. Taormina is full of great restaurants, cafes and fantastic shops.
Taormina is definitely the place to go shopping in Sicily. It has a fantastic mix of classic Italian names you know like Furla and Coccinelle and super cute local stores filled with handmade shoes and handbags.
The Taormina main street is really the best place to go – I didn’t find as many good stores in the back streets. Handbags and purses are the things to buy here.
There are also many places to stock up on tasty Sicilian food products such as olive oil and balsamic vinegar plus lovely streets for strolling and some fantastic restaurants.
13. Bologna
Bologna, Italy is popular as a holiday destination for a variety of reasons. The city has historical appeal, housing the oldest university in the western world.
It also features charming architecture, with over 20 towers dotted throughout the area. As well as numerous grand churches and cathedrals. And some of these historic buildings are home to the loveliest boutique hotels in Bologna.
Although Bologna has a well-preserved historical centre, it still exudes a trendy cosmopolitan character owing to its large student population. Its trendy atmosphere is perfectly complemented by its culinary reputation.
As the capital city of Emilia-Romagna, it forms part of a region with a food history just as old as its celebrated university.
14. Urbino
Urbino is a lesser-known walled city on a hilltop in central Italy. The Palazzo Ducale is the city’s main tourist attraction. The slope opposite the Palazzo offers some of the best views over Urbino.
Urbino is the tiniest Italian town in this post and that is part of its charm. This walled city has many small backstreets that are filled with Italian charm and character.
15. Verona
Home of Opera and Romeo and Juliet lovely Verona also has bags of Italian charm. It is a very walkable city and easy to get around.
The Arena di Verona is a highlight of any trip to this beautiful city in Italy. Visit during the day to get some great photos. I highly encourage you to book opera tickets before you head to Verona.
I am not the biggest opera fan but attending the opera in Verona in this beautiful amphitheater was a very memorable experience.
Climb to the top of Torre dei Lamberti for some fantastic views over Verona and enjoy the square where it is located, Piazza Delle Erbe.
Casa di Giulietta is Juliet’s house. The courtyard area is free to visit but you’ll need to pay if you want to step onto the balcony. Sure it’s a bit cheesy but seeing Juliet’s balcony is a must-do in Verona.
16. San Gimignano
This little town in Tuscany is best known for its nickname of “Medieval Manhattan”. San Gimignano was once home to 72 towers. Today only 15 remain and the highest, Torre Grossa, rises 54 metres. No other tower was allowed to be taller than Torre Grossa in San Gimignano.
17. Trento
Trento is located in the Dolomite mountains in the Trentino-Alto Adige region of Northern Italy. Trento is less frequently visited than many of the other cities in this article but just as beautiful. So you’ll be able to enjoy its sites like Piazza Duomo, the Fountain of Neptune, Casa Cazuffi-Rell and Buonconsiglio Castle without the crowds. The best views of this beautiful city in Italy are from the top of Sardegna – take the short funicular trip to get there.
18. Lecce
Lecce is located down in the heel of Italy in the Puglia region. It is home to a stunning Roman ampitheatre that dates back to 2 AD as well as a 16th century castle. And of course, there is a stunning Piazza del Duomo. Lecce has been nicknamed “the Florence of the South”.
19. Bergamo
Bergamo is close to Milan in Italy’s Lombardy region in the country’s north. The upper part of the city is a UNESCO World Heritage Site and the lower half is a modern city. The Dolomite Alps make for a stunning backdrop. Use the funicular to move back and forth between the upper and lower parts of Bergamo.
20. Pisa
Pisa is of course best known for its Leaning Tower. The Leaning Tower of Pisa sits on the beautiful square Piazza Dei Miracoli in the center of the city.
21. Perugia
This university city is located on the Tiber river in the central Umbria region. Only two hours from Rome, a visit here can be a big day trip or even better spend the night so as to enjoy the old quarter, cobbled streets and don’t miss the public gardens.
22. Siena
Beautiful Siena is one of the highlights of any visit to Tuscany and its medieval heart is a UNESCO World Heritage Site. Its Piazza Del Campo must be one of the most beautiful squares in the world with its golden red-bricked buildings. Piazza Del Campo is also home to the famous 4 day Palio horse race.
23. Cefalu
This medieval town is on the northern coast of Sicily about 70 kilometres east of Palermo. Uniquely its old city lies under a high cliff and is extremely well preserved. Don’t miss Duomo di Cefalu, Tempio di Diana and the beach that is in the town’s centre.
24. Bari
Bari sits on the Adriatic sea and is the capital of the Puglia region in Italy’s south. This vibrant port city is filled with cute cobblestone streets and the lovely Bari Vecchia is its atmospheric old quarter. Enjoy Piazza del Ferrarese, Basilica di San Nicola, Palazzo Mincuzzi and much more.
25. Milan
This beautiful city in Italy’s north is known as the fashion capital of Italy. It is also home to the stunning Piazza del Duomo and the fifth largest Christian church in the world. And don’t miss a visit to Santa Maria dell Grazie to see Leonardo Da Vinci’s The Last Supper painting.
Amanda O’Brien is the creator and editor of The Boutique Adventurer. She has visited 80 countries and is a member of the British Guild of Travel Writers as well as the IFTWTA. She is passionate about wine had has just completed Level 3 of the WSET. Born in Australia, she lives in London.