How to Spend 2 Weeks in Italy: 5 Itinerary Ideas

Not Sure How to Spend 2 Weeks in Italy?

Italy is one of the top three most visited countries in Europe and consistently one of the top 5 visited countries in the entire world! If you are planning a trip to Italy, you are not alone. Many people love exploring Italy’s culture and cuisine, both of which are specific to the region or city within Italy you are visiting.

Italy’s Regions Are All Unique

Over the past three years, my husband and I have spent over 7 weeks traveling in Italy and indulging in all the Italians have to offer! If you’ve been to more than one city in Italy, then you may have noticed subtle differences in the menu offerings, drinks of choice, and people’s sense of urgency.

Rome, the capital of Italy, is home to some of Italy most famous dishes, landmarks, and historical events. On the cuisine side of things, deciding between carbonara, amatriciana, cacio e pepe, and alla gricia may prove to be one of most difficult decisions you’ll have to make while in Rome. On the culture side, you’ll feel the warmth radiating from people as you chat with them over a morning cappuccino or observe locals socializing in the piazzas around town.

Generally, the farther south you go in Italy, the livelier and merrier the people are. All the way down south in Sicily, people chatting in the streets resembles a cheery song. You’ll also find that the meals are simpler and sweets are a bigger part of a standard day of eating. Head the opposite way, up north to Milan, and you’ll notice people are more career driven and well dressed. Restaurants will offer heartier menu options consisting of meats and risottos to combat the colder weather.

5 Different Ideas for How to Spend Your 2 Weeks in Italy

All of these itineraries are structured in a way that makes traveling from place to place a simple a quick experience, so make sure to follow the order from either top to bottom or in reverse.

After you decide which itinerary is for you, make sure to check out all the travel guides below! They’re great for inspiration on where to stay, what to eat, and what to do in each of these towns.

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If you love watching sunsets over the ocean and indulging on seafood while relaxing near the water, than Italy’s coasts are for you! Visiting all five of these places in Italy will ensure your trip is full of sunsets and clear blue waters. Not to mention all the delightful seafood dinners and gorgeous views you’ll experience while following this schedule.

Highlights for this Route –

• Sicily is home of the cannoli, try a freshly filled cannoli and granita too
• Stay in Sorrento as your affordable base camp for the Amalfi Coast
• Eat everything you can in Naples – margherita pizza, spaghetti alle vongole, sfogliatella, and of course cappucinos
• Manarola is a nice town to stay in at Cinque Terre and Nessum Dorma is perfect place for pesto with an ocean view

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Italy is home to some of the most ancient history in the world. If you’re visiting to learn about Julius Caesar’s time in Rome or about how parts of Italy were once under Spanish and Arab rule, then these three cities are perfect for you! Not only will you spend your days walking around open-air museums and observing historic places you may have read about, but you will also get to go in churches, old markets, and museums that showcase the art and culture during the different time periods.

Highlights for this Route –

• Rome has preserved historic architecture amazingly, explore the Colosseum and Roman Forum
• Florence is a beautiful city and tells the story of the renaissance as you walk through the town
• Sicily was once under Arab rule and as a result was the first part of Italy to gain access to sugar

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Italy is known for being a fashionable country. Poorly dressed tourists easily stand out from the crowds of well-dressed Italians going about their daily lives. Northern Italy especially is home to several designer brands such as Prada, Giorgio Armani, Versace, and more. Visiting these cities is the perfect trip if you love luxury shopping and expressing yourself through elevated fashion!

Highlights for this Route –

• Milan Fashion Week occurs twice a year, in February and September
• Celebrities like George Clooney and Madonna have vacation homes on Lake Como
• Florence showcases haute couture fashion and is a perfect place to buy custom fit clothing
• In Rome you’ll find boutique shopping and luxury brands all over town

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If you travel for food, then you need to go to Italy! This is the perfect route to showcases the regionality of Italy cuisine and how fresh, simple ingredients come together to create the most delightful dishes. You’ll get to try pasta, pizza, pesto, risotto, steak, cannoli, and so much more when visiting these cities.

Highlights for this Route –

• Milan is known for their creamy risotto dishes showcasing seafood and vegetables
• Florence has a heartier cuisine full of soups and beans, but don’t forget to try the famous Florentine steak
• Rome is famous for four pasta dishes: carbonara, amatriciana, cacio e pepe, and alla gricia
• Naples is home of the Neapolitan pizza and fresh seafood pastas like spaghetti alle vongole
• Sicily has many sweets to try like cannoli, cassata, granita and more

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The Italian culture is one of the best cultures in the world. Italians are friendly and lively, more concerned with enjoying the little moments of life than stressing over things they can’t control. That being said, Italian culture, like their cuisine, is also very regional. You’ll find southern Italy has a very different culture than central or northern Italy and this route is great to see it all!

Highlights for this Route –

• Sicily is the most laid-back city on this list, some people say their accent is louds like they are singing
• Neapolitans tend to be a bit louder and more chaotic, but their big hearts are always at the center of it
• Rome tends to be a mix of southern and northern cultures
• Lake Como showcases a very sophisticated and regal culture
• Milan may have the most disciplined, work-focused culture of these Italian cities

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This bonus itinerary highlights all the cities I would like to revisit in Italy. I’ve spent several weeks in Italy, but I would love the chance to spend even more time exploring these few areas to indulge in the food again and take in all the beautiful architectures and stunning views.

Highlights for this Route –

• Florence has the “quaint” town feel and boasts amazing dining options and the most beautiful architecture
• Roman pasta is so simple but flavorful at the same time and not to mention the ancient Roman ruins everywhere
• Neapolitan pizza is the best pizza in all of Italy, the soft dough, fresh tomatoes, and mozzarella are chefs kiss
• The views of the Amalfi Coast are unlike any other, the small towns steeped upon ocean cliffs stunning

Pick the Best Route for You!

Italy is my favorite country to visit. Hands-down. And I know it could be yours too! Take some time to reflect on why you love to travel before picking the cities you want to stop at on your Italian vacation to make sure you maximize whatever it is you love about traveling!

Do you like to travel to lounge by the sea and soak up the sun? Then the Italian Coast would be perfect for you! Maybe you are the traveler who plans where they want to eat and not what museums they want to go to? The foodie itinerary would be best for you! Whatever brings you joy in traveling, pick a route that will showcase that for you so you can live out the best Italian weeks of your life!

If you need help deciding which cities are your must-travel-to cities, then check out my travel guides for of the cities! They’re perfect for helping you see what each city has to offer and deciding where you want to spend your vacation.

Click on the cities below to see my travel guide for each place!