How to Spend Two Weeks in Italy

Visit Trevi, a medieval town in the Umbria region, in the spring and catch a glimpse of the poppy fields
Visit Trevi, a medieval town in the Umbria region, in the spring and catch a glimpse of the poppy fields | © Valerio Mei / Alamy Stock Photo
Francesca Masotti

A road trip in Italy is the best journey you can do. From north to south, the country is plenty full of spectacular places that every traveler dreams to see at least once in their lifetime. Be prepared to fall in love with Italy, and, after two weeks spent wandering through the country, it will be hard to say goodbye and head back home.

Day 1 – Venice

Every Italian trip should start with a visit to Venice, the famous lagoon town home to some of the most spectacular landmarks in the country. The best thing you can do here is to wander through the old center and be amazed by old palaces, churches, lovely piazzas, picturesque neighborhoods and magnificent places, such as Saint Mark Basilica, Fenice Theatre, Grand Canal, San Giorgio Maggiore Island, and so on. If you are an art enthusiast, then you can’t miss to visit the Peppy Guggenheim Museum with priceless artworks by the greatest artists.

Day 2 – Milan

Continue your tour and spend some of your time shopping. Which town is the best place for it if not Milan? In the Italian capital city of fashion, it will be very hard not to buy shoes, clothes, bags and other accessories. By the way, beside the fashion, Milan has so much to offer: Don’t forget to see the Gothic Cathedral, The Last Supper by Leonardo da Vinci in Pinacoteca di Brera and Castello Sforzesco. You can visit Milan and enjoy a guided foodie walking tour as part of Culture Trip’s specially curated small-group Northern Italy adventure, led by our local insider.

Day 3 – Turin

Turin is one of the most elegant Italian towns. Located in Piedmont region, it is a true hidden gem that worth a look not only for its historical city center but also for the Egyptian Museum, the second largest in the world behind the Cairo Museum. If you are a history enthusiast, this museum is a must-see once in town. It has also been declared one the most beautiful museums in Europe.

Day 4 – Cinque Terre

Especially on sunny days, there is nothing better to do than go to the beach. One of the prettiest beach locations in Italy is undoubtedly Cinque Terre. These lovely hamlets look like they are straight out of a fairytale. Colored façades, small piazzas, narrow streets and heartbreaking views over the Tyrrenean Sea. With Culture Trip, you can hike along this spectacular coastline on our 10-day Northern Italy adventure.

Day 5 – Tuscany

Finally it’s time to visit Tuscany. This charming region is on the top of this list of destinations to visit in Italy. When you think of green hills, cypress trees, medieval villages, you immediately think of Tuscany. This central Italian region is like a postcard. So take your time, rent a car and get lost in the Tuscan countryside.

Day 6 – Florence

If you want to combine nature and art, then you need to go to Florence. The Tuscan capital city is surrounded by spectacular countryside that can be reached in a few minutes from the city centre. Once here, you can’t avoid the historical center of Florence, no matter if you hate the crowds. To admire the beauty of the town climb, to the top of the dome’s cathedral and be prepared to be amazed by stunning views.

Day 7 – Umbria

After the crowds of Florence, there is nothing better than head into Umbria, a beautiful region often avoided by tourists, who are more attracted by the famous Tuscany. But Umbria worth a visit for its nice hamlets, such as Gubbio, Norcia, Spoleto, and for its lively capital city, Perugia.

Day 8 – Assisi

The sacred city dedicated to Saint Francis, the saint patron of Italy and Europe. Be prepared to fall in love with this ancient city and also to fight with a lot of tourists from all over the world, here to admire the spectacular cathedral.

Day 9 – Le Marche

Another hidden gem of Italy, Le Marche region really worth a visit. Nobody knows that Le Marche is home to fabulous sandy beaches and lovely ancient hamlets away from the crowds and tourists. If you are looking for quiet and peace, there is no best place to visit than this region. If you only have one day, just go to Monti Sibillini, a natural area near Umbria.

Day 10 – Rome

Rome sweet Rome! Be prepared to visit one of the most spectacular cities in the world, the one and only Rome. Colosseum, Castel Sant’Angelo, Vatican City, Trastevere, Imperial Forum and so on. Finally you’ll see with your eyes all these amazing landmarks famous worldwide.

Day 11 – Naples

It’s pizza time! Naples is the best destination in Italy for food. If you think you already know what pizza is, well, trust us, you’ll change your mind. But Naples is not only a pizza spot, it is also an amazing town with unique buildings, such as Castel Nuovo and Teatro San Carlo, and wonderful sea views.

Day 12 – Caserta

Had you ever dreamed you’d live like a prince or a princess? Well, if yes is the answer, you have to visit the stunning Reggia of Caserta, this palace is one of the most beautiful architectural structures of the south of Italy and worth a visit.

Day 13 – Palermo

The last stop of your Italian tour is Palermo. The capital city of Sicily is a perfect mix of Arabic, Baroque and Normand architecture. Once in town, don’t forget to spend some of your time in the Ballarò market, the most famous food market of Italy, and taste some of the typical Sicilian delicacies, such as arancino and pani ca’ meusa (a special panini made with milt). Enjoy a guided walking tour and Sicilian cooking class in Palermo on our action-packed 10-day Sicily adventure.

Day 14 – It’s time to say Goodbye

It’s never easy to say goodbye to Italy, but don’t be sad, you can always buy a ticket and go back another time: Italy welcomes you with open arms every time.

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

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