Since living in Florence in 2016, I've been back to visit twice. There's so much to love about the city, which is the capital of the Tuscany region. For those visiting for the first time, I recommend staying a minimum of four full days to explore the city's museums and local markets.

For example, I love visiting the farmers market in Santo Spirito for fresh-baked goodies, local produce, and vintage finds.

I've also enjoyed grabbing gelato and trekking up to Piazzale Michelangelo to watch the sunset. On cooler evenings, St. Mark's Church is a great place to watch affordable live opera.

Outside the city, I suggest horseback riding through the Tuscan hills, attending a pasta making class, and taking a wine tour.

I immediately fell in love with how enchanting, quaint, and walkable Verona felt during my first visit in 2016.

Home to Shakespeare's beloved "Romeo and Juliet," visitors commonly visit Juliet's house, calling down to those below from the balcony.

During my time in Verona, I stumbled upon Club di Giulietta, a volunteer group that calls themselves the secretaries of Juliet. They receive thousands of letters addressed to Juliet from around the world, and volunteers sort letters by language before handwriting a response.

I got to spend a few hours reading and writing replies myself, which became the highlight of my trip to Verona.

Overall, the city's walkability, history, and quaint feel make it perfect for a day trip for time-restricted itineraries.

If Sicily is on your itinerary, a trip to Catania is a must. The city is at the foot of Mount Etna, the highest active volcano in Europe.

In fact, the volcano is integral to local tourism, architecture, and wine production. Guides offer hiking tours during dormancy, allowing visitors to walk the crater rim. The volcanic stone is also used to build local churches, plazas, and roadways.

Sicily's food and wine scene is also reason enough to visit this part of Italy. The volcanic ash can help enrich the soil, providing nutrients for vineyards that produce incredible wine.

Cinque Terre is a string of five seaside villages on the northwestern coast of Italy.

Although all five villages are accessible by train, hiking between them is a popular activity. I'd recommend starting in the southernmost town, Riomaggiore, and hiking north for stunning views.

Cinque Terre is perfect for anyone looking to relax in a vibrant environment, enjoy traditional Italian culture, or explore five seaside villages in one day.

Fellow travelers warned me that Naples fell short of their expectations, but I wanted to experience the city for myself. So, I visited twice during a solo trip last year, staying on opposite sides of the city each time.

Although the Neapolitan pizza did not disappoint, navigating the sprawling, hilly city on foot was challenging.

The local metro system was convenient for getting around, but it turned out to be a persistent target for pickpockets. After witnessing a few such instances firsthand, I made the choice to avoid taking the trains at night. However, that meant my taxi fares added up quickly after evenings spent out.

Overall, if I'm going to be in Southern Italy I'd much rather pop over to the Amalfi Coast or other nearby destinations.

There's a lot to love about Venice, from the unique architecture to the outstanding glasswork.

Unfortunately, though, I was underwhelmed by the food and noticed some things like souvenirs, meals, and experiences were more expensive than they were in other Italian cities I'd visited.

Although the architecture is stunning, the narrow, winding streets also made it difficult to navigate the city and added to the feeling of overcrowding.

Additional planning is now needed to visit, as the city requires tourism permits on certain days. Considering the expense, challenges with walkability, and additional planning required, I likely won't return to Venice for another visit.

This story was originally published on May 3, 2025, and most recently updated on October 16, 2025.