Italy is a top bucket list destination for many travelers thanks to its distinct history, culture, architecture, and food. This romantic European country is surprisingly diverse, with landscapes ranging from quiet fishing villages to bustling metropolitan cities and towering mountain peaks. With so much beauty to discover, deciding what cities in Italy to visit during your trip can feel overwhelming.

Regardless of how and where you spend your time in Italy, you won’t regret experiencing this enchanting vacation spot. Let the winding streets transport you to the era of the Roman Empire, or imagine you’re an A-list celebrity escaping the paparazzi at a luxurious beach resort. Italy’s iconic major cities will exceed all expectations, leaving you with precious lifelong memories.

Bellagio

Bellagio is one of the most beautiful places in the Lake Como area. It’s incredibly picturesque, with winding cobblestone streets, elegant architecture, and stunning views of the lake and surrounding mountains.

Pretend to be a millionaire for a day by renting a boat and hitting the water to snap photos and admire the opulent homes overlooking Lake Como. Once you’ve worked up an appetite, indulge at Alle Darsene di Loppia before retiring to your accommodations at Hotel du Lac. Bellagio is easily accessible from Milan, making it the perfect day trip or weekend getaway.

Venice

You can’t miss the bucket list-worthy city of Venice during your next trip to Italy. While it can be touristy, seeing the Floating City in person is worth battling the crowds.

“If you are going to visit in summer, the high season, avoid mid-day when it can be hot and crowded and instead, take a day trip to Padua, a hidden gem about 30 minutes by train which has a lot to see and offers a welcome respite from the crowds,” suggests Daria Bachmann of The Discovery Nut. “Come back to Venice in the evening to enjoy dinner and walk around when it’s not too hot.”

Can’t-miss attractions include Doge’s Palace, St. Mark’s Square, Rialto Bridge, and San Marco Basilica. Venice also boasts many renowned restaurants — try Osteria La Bottega Ai Promessi Sposi for classic Venetian specialties or splurge at Ristorante Quadri. Meanwhile, the 5-star Hotel Danieli Venezia is a fabulous home base for your Venice adventures that will make you feel like royalty.

Palermo

Palermo is the capital of Sicily, the largest Mediterranean island off the southern Italy “boot.” Many consider it among the most beautiful cities in Italy for its miles of beaches and distant volcanic peaks. Centuries-old cathedrals and palaces line the Palermo city streets, allowing visitors to step back in time.

Pack a tote with your swimsuit, water, and other beach day essentials to take advantage of Palermo’s waterfront areas. Mondello Beach and Spiaggia Vergine Maria are top choices for sunbathing and swimming. After enjoying some fun in the sun, grab a bite to eat at Taverna Dei Canti, Nonna Dora, or Bisso Bistrot, all famous for their seafood and pasta dishes.

Rome

Every Italian trip itinerary should include a stopover in the Lazio region to see Rome. The Eternal City offers an incredible variety of things to see and do, including world-famous sights like the Colosseum and the Trevi Fountain.

“Rome is my favorite city in the world, but being able to escape the crowds is key to having an enjoyable time,” says Abby Price of Summit Skier. “My favorite tip is following the five-minute rule. This means walking five minutes from any attraction before picking any restaurant, cafe, or bar. If you can walk away from the attraction, you’ll typically find a much less touristy and expensive spot.”

You must sample the city’s pasta offerings to immerse yourself in Roman culture and cuisine. Local favorites include La Taverna dei Fori Imperiali for bucatini all’Amatriciana and Antico Forno Roscioli for pasta alla carbonara.

“My top recommendation in Rome is Ristorante Pinseria Da Massi,” Price shares. “They serve incredible steak, cacio e pepe, and tonnarelli.”

After dinner, finish your day of sightseeing with freshly scooped gelato from Giolitti or Della Palma.

Cinque Terre

Head to the Italian Riviera to experience the postcard-worthy area of Cinque Terre. This UNESCO World Heritage Site comprises five centuries-old seaside villages. Cinque Terre’s captivating waterfront views and colorful homes draw visitors from all over the world.

A boat ride is an excellent way to admire Cinque Terre and gain a new perspective on the region. Other popular activities include hiking, sunbathing on the beach, and tasting locally-made wines.

Like most areas of Italy, Cinque Terre has many mouthwatering restaurant options. Enjoy a romantic sunset dinner at La Torre Aurora in Monterosso or a fresh seafood lunch at Trattoria dal Billy in Manarola.

Florence

Art and history lovers will have fun in Florence, the ancient capital of Tuscany. Around every corner, there are countless galleries, museums, and historical sites to discover. Whether you plan to wander around at your own pace or join a guided tour, expect to be awestruck by Florence’s architecture and scenery.

The Uffizi and Accademia Galleries are essential attractions in Florence. Here, you can spend an afternoon admiring works by famous artists like Michelangelo and Leonardo da Vinci. Public city squares such as Piazza del Duomo and Piazzale Michelangelo are also fascinating to explore.

Once you’ve worked up an appetite, indulge in the province’s incredible culinary scene. Try the bistecca alla Fiorentina at Ristorante Parione, or go all out at Winter Garden by Caino, a Michelin-starred restaurant. Winter Garden is in the St. Regis Florence, a chic luxury hotel worth splurging on for your stay.

Amalfi

Summer may be the most popular time to visit Amalfi, but the city also shines during the off-season. Fall and winter offer cheaper accommodations, fewer crowds, and seasonal events. The colder months let you discover a side of Amalfi that most tourists miss when visiting in summer.

Amalfi is located among dramatic seaside cliffs, adding to its Old World aesthetic. Spend your time in the enchanting city admiring historic attractions such as the Duomo di Amalfi, Piazza del Duomo, and Museo della Carta. Once hungry, consider grabbing a bite at the well-reviewed Pizzeria Donna Stella or Da Maria.

Stay at La Bambagina, a quaint bed and breakfast in the heart of the city. Remember that you may have to navigate tight staircases and uneven cobblestone paths. While this adds to Amalfi’s charm, it can be frustrating to realize upon arrival if you haven’t planned or packed accordingly.

Milan

Italy’s premier fashion destination, Milan, is always exciting and energetic. The capital of the Lombardy region is a cultural hub famous for its luxury stores and impressive cityscape. Milan’s stunning Duomo rivals iconic cathedrals like Notre Dame in Paris. Its intricate, over-the-top design will have your jaw on the floor throughout your visit.

In Milan, you can see da Vinci’s iconic Last Supper mural in the Convent of Santa Maria Delle Grazie and browse designer brands at Galleria Vittorio Emanuele II.

Shopping in Milan is very different from in the United States — instead of chain stores like Anthropologie, you’ll find charming boutiques and rows of opulent high-end shops.

For a more unconventional afternoon activity, head to San Bernardino alle Ossa. This small church is well-known for its morbid chapel adorned with human skulls and bones.

Saturnia

Saturnia is an underrated gem where you can enjoy natural hot springs. Many go to Terme de Saturnia, an exclusive resort with artificial pools. However, Cascate del Mulino provides a more authentic hot springs experience. Skip the expensive hotels and rent a local apartment or home to save money and see a quieter side of Saturnia and its surrounding villages.

Since the hot springs stay warm year-round, Saturnia is always ideal for a day or weekend trip. Be warned that you might see tiny bugs swimming in the waters at Cascate del Mulino, depending on the season. They’re completely harmless and easy to overlook as you savor the soothing hot springs.

Cascate del Mulino is free and open 24 hours a day, seven days a week. Plan to arrive early, around sunrise, for spectacular views and minimal crowds. Otherwise, you’ll compete with fellow tourists for a spot in the springs.

Bologna

While Bologna isn’t as glamorous on the surface as other Italian cities, it provides a welcome escape from the typical tourist crowds. As the capital of the Emilia-Romagna region, Bologna is a food lovers’ paradise. Sample delicacies like prosciutto and parmigiano reggiano at the many exceptional eateries citywide.

A walking tour is ideal for familiarizing yourself with Bologna and its top sights. Dive into local history by visiting the Two Towers, Basilica di San Petronio, and the International Museum and Library of Music. Afterward, grab lunch at Mercato delle Erbe, an indoor food market, or one of the restaurants lining Piazza Maggiore.

Many companies in and around Bologna offer food tours, where you can learn how items like balsamic vinegar and prosciutto are made and taste the delicious creations. If you’re still hungry after the tour, grab dessert at Cremeria Santo Stefano and a nightcap at Ruggine, a popular cocktail bar.

Pompeii

Walk through the Pompeii ruins to fulfill a lifelong travel bucket list item. Seeing the remnants of a once-thriving city frozen in time and preserved under ash is unforgettable. You need at least half a day to wander through the sprawling UNESCO World Heritage Site.

For a seamless Pompeii visit, download offline Google Maps to identify landmarks as you encounter them throughout the ancient ruins.

An entry fee is required to explore Pompeii, and you can only purchase official tickets on-site at the entrance or TicketOne. Avoid other companies and websites claiming to sell Pompeii packages, as the prices are likely marked up, and the tickets may be fake.

If you have extra time after touring Pompeii, it’s a short and easy drive to Naples. You can enjoy waterfront views here and grab a slice at a famed local pizzeria. Popular restaurant options in Naples include L’Antica Pizzeria da Michele and Gino e Toto Sorbillo.

Positano

Consider adding the charming coastal village of Positano to your Italy itinerary. This glamorous resort destination boasts a rich cultural heritage, fine dining, excellent shopping, and picturesque scenery. It’s the ideal place to unwind and live out your dreams of living on the Amalfi Coast.

“If you’re looking for the perfect Positano experience, have lunch at Chez Black,” Jessy Hamel of Brighter Things Planning recommends. “They’re right on the beach, and the food is incredible. Enjoy a limoncello with waves crashing in the background and pretend you’re a local for a little while.”

Given its small size, Positano makes a fantastic and convenient day trip from Naples. Treat yourself to a night at Il San Pietro di Positano, an opulent 5-star hotel overlooking the coast.

Website | + posts

Elise Armitage is the founder of What The Fab, a travel + lifestyle blog based in California, founded in 2012. At the beginning of 2019, Elise left her corporate job at Google to chase her dreams: being an entrepreneur and helping women find fabulous in the everyday.

Leave a Reply