Darby's Destinations Luxury Travel - Italy

Which Italian city should you visit next?

No two cities are the same in this small Southern Eruope nation

July 8, 2022

Italy is one of Europe’s most diverse countries with an expansive range of sights, cuisine, and landscapes. Knowing which city you should start your trip in is the first hurdle to overcome. Here is a guide to determining which Italian city is best for you for your next – or first – vacation.


Located in the glorious region of Tuscany, Florence stuns with its renaissance architecture, landscaped gardens, and art galleries. Pay a visit to Giardino di Boboli for majestic views over the surrounding hills. The Duomo di Firenze occupies the core of the city while the Ponte Vecchio is an icon and a premier spot for souvenir shopping. Art fans will want to visit the Uffizi Gallery as well as the Accademia Gallery of Florence for the opportunity to see Michelangelo's David.

Best for: Art and culture, slow pace, families


Italy’s electrifying capital city is bursting at the seams with historical attractions including the Colosseum, the Roman Forum, the Pantheon, and Vatican City with its Sistine Chapel. When you’re not busy exploring the sights, the city contains plazas and monuments such as the Spanish Steps and Trevi Fountain where you can savor a scoop of gelato and soak up the atmosphere. Foodies should spend time exploring the trattorias of Trastevere while the seaside neighborhood of Ostia will delight children and beach lovers.

Best for: History, food, nightlife  


Fashionable Milan is one of the wealthiest cities in Italy and is teeming with stylish boutiques, galleries, upscale restaurants, and deluxe hotels. Leonardo da Vinci’s Last Supper is open to the public, located in its original setting at the former Dominican convent of Santa Maria delle Grazie. Experiencing a show at La Scala Opere is an unparalleled experience.

Best for: Food and drink, shopping


Sitting in the Bay of Naples with a direct view of Mount Vesuvius, Sorrento is the perfect base to plan trips to the volcano as well as the archaeological zones of Pompeii and Herculaneum. You may also take day trips to the island of Capri – or spend the night on this luxurious isle – as well as the Amalfi Coast and explore the abundant lemon groves where limoncello is produced.

Best for: Families, beaches, romantic escapes


This truly unique city is built atop a lagoon and is distinguished by its tranquil and picturesque waterways. Piazza San Marco and Saint Mark's Basilica mark the heart of the city and you’ll not fail to feel enchanted by the city’s architecture when you take a ride on a gondola. Further afield, you’ll appreciate an entirely different perspective of Venetian culture from the Murano and Cannaregio districts.

Best for: Architecture, romantic escapes


The island of Sicily warrants a trip in its own right and this small city on the southeast coast is a great place to start your Sicilian exploration. Spend time exploring the medieval streets of the Island of Ortigia, filled with small boutiques, cafes, and taverns. The Neapolis Archaeological Park where you’ll find remains of an Ancient Greek theater as well as Roman artifacts and sculptures. Syracuse is the best place to sample cannoli – a Sicilian staple – alongside fresh seafood and artichokes.  

Best for: Off-the-beaten path, food, beaches

Italy is one of my specialist areas. Contact me and we can discuss your perfect itinerary to this country of history, culture, islands, and dramatic landscapes.

Ready to embark on your own journey to the extraordinary?