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Italy needs no introduction at all. For centuries, this stunning Mediterranean country has captured the hearts of travellers all over the globe, including mine. Italy is known for many things, including its rich history, love for food and wine, and groundbreaking architecture, to name just a few. 

There’s a lot to love about Italy. When I’m asked about my favourite country, I often mention Italy. I’ve been there more times than I can count, and it’s safe to say that it has a special place in my heart. 

With so much to look forward to, it can be incredibly overwhelming to decide what to include and sadly leave out in your Italy itinerary. So, I’ve broken down some of my favourite highlights about this much-loved country.

Italian Cities 

There are 20 regions in Italy so, as you can imagine, there are countless beautiful cities in Italy. I’m sure we’d love to visit them all, but here’s a quick round-up of some of the best ones worth visiting. 


They say that all roads lead to Rome, and once you’re there, it’s easy to see why. “The Eternal City” stands as a testament to one of the most powerful empires in the world and has impressed millions of people throughout the centuries. 

Nested along the River Tiber, Italy’s vibrant capital is as romantic as it is charismatic. While it might seem cliche, if you’re visiting Rome for the first time, then I’d suggest visiting its top sights like the majestic Colosseum, Trevi Fountain, and the Pantheon. 

There are also loads of facts about Rome and its many monuments that are sure to impress you, like the fact the city has over 2,000 fountains. 


Many people might consider Milan a very structured and less charming city because of its business-minded approach. To be fair, it’s not easy being the hub of the Italian economy. 

Still, apart from its seriousness, Milan is a beautiful city with touches of architectural brilliance displayed in buildings like the Piazza del Duomo.   

Let’s remember that it’s also the fashion capital of Italy and one of the most fashion-forward cities in the world. It might not come as a surprise to you then that Milan is home to the oldest shopping mall in the world, the Galleria Vittorio Emanuele II. 

This gem of a building houses some of Italy’s most iconic brands, such as Prada, Versace, Gucci, and Armani, so it’s worth checking out even if you don’t buy anything.


Florence – the beating heart of Italy’s beloved Tuscany region. Nicknamed “The Renaissance City,” I think hard not to fall in love with Florence. 

Home to iconic galleries such as the Uffizi Gallery, masterpieces from Michelangelo, and countless museums, there’s a lot to enjoy in Florence. And for all food and wine lovers, I’m happy to tell you that this is one of the best places where you can enjoy Tuscan cuisine, wine, and gelato. 

As you explore the beauty of the city, you’ll find that Florence is a great place to do some shopping. There are so many markets where you can bargain on handmade leather items and other mementos. 


Sitting in “the Heel” of Italy’s boot, Lecce is not only one of the most stunning cities in the Puglia region but also in the whole of Italy. Nicknamed the “Florence of the South,” Lecce is a unique city with Baroque-style buildings. 

This place will transport you back in time, with stunning cobblestone streets, plazas, quarters, and buildings with intricate limestone designs. If you make your way to Lecce, explore its idyllic Old Town, along the coast and Roman Amphitheater.


Naples is the birthplace of a food that so many of us love – pizza. Nestled between Mount Vesuvius and the Bay of Naples, this is one of the most beautiful seaside cities. 

Its waterfront area displays a row of colorful houses, and with the backdrop of the blue waters of the Med, it’s not hard not to fall in love with Naples. 

With sweeping visas across the Bay, Naples is a gateway to the gorgeous Capri Island and Pompeii. 


Venice is just one of those cities that immediately pop into your mind when you think about Italy. Like many other Italian cities, Venice has been capturing the hearts of its visitors for centuries. 

A fact about Venice that some people might not know is that it’s much more than just one island. It’s made up of over 100 smaller islands in a lagoon and interconnected by canals.

Its majestic grand palaces (yes, there’s more than just Doge’s Palace), iconic Grand Canal, squares, and stunning buildings all give a glimpse as to why the city continues to tug at the heartstrings of many. 


The city of Orvieto, in Umbria, is not as big and as flashy as some of the other Italian cities, but that doesn’t make it any less special. This small walled city sits on top of a towering hill and has some of the most breathtaking views in the country. 

Olive groves, vineyards, and cypress trees are just some of the features surrounding the city, making it super scenic. This lovely city is less than a two-hour drive from Rome, so it’s the perfect place to escape for a day trip and enjoy the region’s best wine. 

While wine tasting is one of the main things to do in Orvieto, the city is extremely explorable by foot, with lots of hidden gems to discover. 


Italy’s stunning “White City,” Ostuni, is one of the best places to visit in Puglia and all of Italy because there’s simply no place quite like it.

Its iconic whitewashed buildings sit on a hilltop that overlooks the incredible Valle d’Itria countryside and the wonderful Adriatic Sea. It’s a really laid-back city, and everyone does things at their own pace. 


Tucked away in the Tuscan countryside, Montepulciano is any wine lovers heaven. There are many wineries in Montepulciano that mainly produce the region’s star export, Vino Nobile di Montepulciano.

The city is renowned not only for its wine but its gorgeous scenery and historic old town. It’s only 90 minutes away from Florence, so if you’re looking for a sweet escape, Montepulciano should be on your list. 


Positano will no doubt be on your list if you travel down to the gorgeous Amalfi Coast. There are a lot of things to do in Positano, apart from swimming in the stunning blue waters, and my guide takes you through them. 

Italian Landmarks Not to Miss 

There are 20 administrative regions in Italy, with countless cities and towns. So, that means that there’s an overwhelming amount of landmarks. There are a few, though, that stand out, so here are a few famous landmarks in Italy to add to your bucket list. 

Trevi Fountain

There are many fountains in Rome, but the one you’ve probably heard the most about is the Trevi Fountain. This Baroque masterpiece was created in the late 17th century and has stood the test of time. 

According to legend, if you drop some coins into the fountain, you’ll receive good luck. While I don’t know how true this is, it’s worth a try. 

The Colosseum

Built around 70 AD, the Colosseum was built to impress. And even though it’s sustained some damage over the centuries, it continues to amaze all who catch a glimpse of it. Sitting in Rome’s city center, the Colosseum remains the largest amphitheater ever built and serves as a symbol of ancient Rome’s power and might. 

The Pantheon

The Pantheon is one of the oldest structures and top monuments in Rome, first built in 25 BC for Roman gods. After surviving a devastating fire, it was rebuilt by Emperor Hadrian around 126–128 AD. 

It’s one of the best-preserved monuments in Italy and has served as the inspiration for many builts across the globe. 

Leaning Tower of Pisa

We’ve all heard of the Leaning Tower of Pisa, mainly because it’s one of the most unusual structures in the world. This building, made from limestone, marble, and stone, stands at a staggering 56 metres, tilted at an angle of about four degrees. 

Despite a design and construction flaw, it still stands as a testament to the ancient Romans’ skill and ingenuity and is one of the most well-preserved buildings in the world. 

Mark’s Basilica

St. Mark’s Basilica is one of Venice’s star landmarks. Built to house the remains of the patron Saint Mark, this church has survived a fire and shown extreme resilience. 

Today, you’ll see incredible Byzantine architecture on the exterior and immaculate paintings and other ornate details on the interior. 

Italy Itineraries 

As I’ve mentioned before, it can be really hard trying to decide what to do when you’re planning a trip to Italy. Especially for a first-time traveller. If you’re looking for some inspiration to get going, here are some of my itineraries to help you. 

Ultimate 10-Day Itinerary 

Spending 10 days is an ideal amount of time to see most of what you need to see. My 10-day Italian itinerary includes the major cities and stops like Rome, Venice, and Naples, along with some handy tips to make your journey as stress-free as possible.

7-Day Sicily Itinerary 

If you’ve got your heart set on visiting one place specifically, then have a look at this 7-day Sicily itinerary. If you’re sold, have a look at the best boutique hotels in Sicily to book your stay. 

Other Things to Do in Italy 

Many people don’t always think of Italy as a place where you can go on a skiing holiday right away. However, the Italian Alps and the Dolomites have some of the best ski resorts in Italy and in Europe, which can make for an epic winter holiday.