No, you can’t just visit Italy in five days and six nights.
You go. And then you go again.
And then again.
And still—you haven’t even begun.
Italy isn’t just a place; it’s a feeling, a way of life, an addiction. Every region tells a different story—the pasta in the north is not the pasta in the south, tiramisu belongs to one place, focaccia to another, and the islands serve lemon sorbet so fresh it feels like the sea itself.
So where do you start?
Maybe the Italy that everyone sees.
Maybe the Italy that few do.Either way, you’re going to fall in love.
The More Traveled Path 🏛🍷🚆
Milan → Florence → Bologna → Verona → Venice → Rome
Milan: The Start of the Affair
Milan doesn’t beg for attention. It doesn’t need to. You step into the city, and it simply lets you discover it on your own.
Walk. Get on a tram. Walk some more. This city was made for movement, and you feel its pulse as you wander.
Climb to the rooftop of the Milan Duomo. From up here, the city stretches out before you, rooftops blending into the horizon. It feels endless. Then come back down, grab a cone, and drown yourself in gelato.
If you have time, learn about the hidden Peter Pan stories of Milan. Every street holds a secret. This city rewards the curious.
When you’ve had enough of Milan’s energy, Florence will slow you down.
Florence: The City That Feels Like Art 🎨🏛
Florence is not just a city—it’s a masterpiece. It looks sculpted, not built.
Walk past the dome of the cathedral, past stone bridges, past hidden courtyards. Michelangelo’s David stands in quiet perfection, and you will stand there longer than you expected.
In the evening, climb up to Piazzale Michelangelo and watch as the sun sinks behind the terracotta rooftops. It is the kind of view that stays with you forever.
For dinner, find a tiny osteria tucked away from the main streets. Order the mushroom pasta at Vini e Vecchi Sapori. No tourist menu. No pizza. No nonsense. Just real, comforting Italian food.
Before you leave, learn about Dante. His love, his poetry, his obsession with Florence. Walk the streets he once walked. See the city through his words.
The next morning, it’s time for Bologna.
Bologna: The City of Gelato & Porticoes 🍦🏛
Bologna wraps you in warmth. The endless porticoes, the deep orange walls, the smell of fresh pasta in the air—it’s a city that feels like a hug.
And the gelato? The best I’ve ever had. Creamy, smooth, perfect.
Walk under the porticoes. Bologna has over 40 kilometers of covered walkways, a city where you can walk for hours without ever getting wet in the rain.
If you have time, take a detour to the University of Bologna—the oldest in the world. This is a city that has seen centuries of knowledge, and you can feel it in the air.
When you’re ready, head to Verona—the home of Romeo and Juliet.
Verona: Where Tiramisu Was Born 🎭🍰
Verona is pure poetry. It doesn’t matter if you believe in the story of Romeo and Juliet—just walk the city, and you’ll feel the romance anyway.
Yes, the balcony is touristy, but why not stand under it? Why not leave a note on the wall? Why not pretend, just for a moment?
Then, go find the best tiramisu of your life. Because this is where it was born.When you’re done, take the train to Venice.
Venice: The Floating Dream 🚤🏠
Venice isn’t real. It’s a dream that somehow exists.
The city rises from the water, its streets made of canals, its buildings reflections of centuries gone by.
Stay inside the city, not outside. If you don’t, you won’t really experience Venice.
Walk without a map. The best way to see Venice is to get lost.
Take a boat to Burano, the island of colors. A town so photogenic, it feels like stepping into a painting.
Then go to Murano. Watch artisans shape glass with fire, turning it into something almost magical.
Finally, take a train to Rome.
Rome: The Eternal City ⏳🏛
Rome isn’t just a city—it’s an era, still alive.
Walk through the Forum Romanum, where ruins stand frozen in time. Stand in front of the Colosseum, and feel the weight of history.
📸 Pro tip: Take a photo from Forum Romanum—this gives you the best Colosseum shot.
🏛 Get the Membership Card for Parco Archeologico del Colosseo.
- Unlimited access.
- Skip the lines.
- Best, least crowded views of the Colosseum.
Go to the Vatican early. If you want a photo of the Sistine Chapel without people, you need to rush there first.
Look out for orchestra events in the churches. If you hear Elgar’s violin, just sit, close your eyes, and let it carry you.
🌅 Catch the sunset at Ponte Sant’Angelo. Rome looks best bathed in golden light.
Book all your tickets early. In Italy, nothing is convenient on the spot.
And if you want fewer crowds, go in late April, early May, or September.
The Less Traveled Path 🚗🌊🧀
Rome → Matera → Polignano a Mare → Altamura → Ostuni → Alberobello → St. Lucia
Welcome to Puglia.
Home of:
🧀 Burrata.
🧀 Mozzarella.
🧀 Stracciatella.
🍞 DOP Focaccia.
Matera: The City of Stones 🏡
🚗 Rent a car. Drive. Live the Italian dream.
🏡 Stay in a cave house. Matera is 9,000 years old. The homes are carved into the cliffs.
Polignano a Mare: Cliff Diving & Blue Waters 🌊
Stop wherever the road calls you. Jump into the water whenever you feel like it.
🏊 Cliff dive. The best waters are the ones you don’t plan to swim in.
Altamura: The Bread & Cheese Pilgrimage 🧀
🥖 Try the DOP focaccia. Best bread. Period.
🧀 Take a cheese-making tour with Dicecca. Learn how to make burrata, mozzarella, stracciatella.
Italy: The Country You Keep Coming Back To
You won’t see everything.
You can’t.
But you don’t need to.
Because Italy isn’t meant to be checked off a list.
It’s meant to be felt.
And once you go?
You’ll go again. And again. And again.
Because Italy never really lets you go.