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The good news?

You’ve finally found the time to go to Italy and live out your la dolce vita fantasies!

The bad news?
YOU’VE ONLY GOT FIVE DAYS TO SEE AS MUCH OF THE COUNTRY AS POSSIBLE.

Maybe it’s a short trip, or perhaps Italy is part of a larger visit to Europe, and five days is the most that you can dedicate to this land of pasta, pizza, and the Aperol spritz.

The goal, then, is to see as much of the country’s character as possible, while being economical with your time.

You’ll want to prioritize your time for only the most worthwhile experiences.

DOES THAT INVOLVE HITTING THE BEST ART MUSEUMS, OR HAVING YOUR FILL OF THE BEST PASTA AND WINE IN EACH REGION?

Only you can define which experiences will make your heart sing, but I can help you map out the best route through Italy in 5 days.

I’ll also tell you why it’s ok to leave a few places off of your itinerary, so that your trip won’t be weighed down by traveler’s FOMO (or fear of missing out).

So let’s get into it, because you don’t have a lot of time and we want to make sure that your 5 days in Italy are lived to the fullest!

The Ultimate 5 Day Italy Itinerary For Your Next Visit

Day 1 – Rome

Take a guided tour of the Colosseum and Roman Forum to kick off your trip

Wander through the historic center with stops at the Pantheon, Piazza Navona, Trevi Fountain, and the Spanish Steps

Enjoy a Wine & Food Tasting Dinner at Rimessa Roscioli, one of Rome’s best spots for regional pairings and storytelling

START YOUR ITALIAN ADVENTURE WITH A TWO NIGHT STAY IN THE ETERNAL CITY.

You’ll dedicate one entire day to Rome and then see the major sites of adjacent Vatican City (technically its own microstate) on day two.

A guided tour is the best way to experience the history and drama of the Colosseum and Roman Forum.

Other landmarks, though, like the Panteon, Piazza Navona, Trevi Fountain, and the Spanish Steps are fine for you to explore on your own.

If you like a little bit of structure to your wanderings, I’d recommend Rick Steves’ audio tour of Rome.

IN THE EVENING, I’D RECOMMEND THE WINE TASTING DINNER AT RIMESSA ROSCIOLI.

It’s a food and wine journey through Italy and its diverse gastronomic regions, and a great way to end your first night in Italy.

Day 2 – Vatican City

Start the day with an early entry tour of the Vatican Museums and Sistine Chapel
Explore St. Peter’s Basilica and climb the dome for panoramic views over Rome
Sip a rooftop aperitivo near the Vatican just before sunset
Enjoy dinner near Piazza Cavour in Rome’s Prati neighborhood, known for its local vibe and great restaurants

On your second day in Rome, head to Vatican City to see the artistic treasures of the Catholic Church and learn about the role of the church over centuries of European history.

Book early access to the Vatican Museums to avoid the worst of the crowds and really take in masterpieces like the Raphael Rooms and the Sistine Chapel ceiling.

AFTER THAT, HEAD INTO ST. PETER’S BASILICA, JAW-DROPPING IN ITS SCALE AND DETAILS.

If you’re up for it, climb to the top of the dome for unrivaled views of Rome.

In the afternoon, leave behind the busy corridors and Baroque artwork for a peaceful rooftop aperitivo with views over the city.

Terrazza Les Étoiles is my favorite rooftop spot!

Wrap up the day with dinner in the elegant Prati neighborhood, where the crowd skews more local than touristy.

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Day 3 – Florence

Visit the Duomo and climb Brunelleschi’s Cupola for stunning views
Visit the Accademia Gallery to see Michelangelo’s David in person
Explore Renaissance masterpieces at the Uffizi Gallery in the afternoon
Watch the sunset from Piazzale Michelangelo after walking across the Ponte Vecchio

The train from Rome to Florence only takes about an hour and a half, so I suggest you wake early on day 3 to depart for Tuscany.

Florence is compact, walkable, and absolutely packed with some of Italy’s best examples of Renaissance art.

Start your day at the Duomo, with its green and pink exterior and the engineering marvel of its dome.

HERE, TOO, YOU CAN CLIMB TO THE TOP OF THE DOME FOR AMAZING VIEWS OF THE CITY.

Next, head to the Accademia to see Michelangelo’s David (yes, it really is that impressive in person), followed by an afternoon at the Uffizi Gallery.

If you’re an art history lover, you’ll be in heaven — and if you’re a casual observer, you’ll see up close the great riches of Florence that were bequeathed to the city by the last Medici heir.

Make your way across the Ponte Vecchio and head up to Piazzale Michelangelo for sunset — one of the most iconic city views in all of Italy.

FOR DINNER, I RECOMMEND HEADING TO CIBRÈO CAFFÈ, THE COZY LITTLE SISTER OF CIBRÈO RISTORANTE, AND ORDERING THEIR FAMOUS TAGLIATELLE CACIO E BURRO.

THERE ARE A COUPLE WAYS TO STRUCTURE YOUR TWO LAST DAYS IN ITALY.

This mostly depends on how adventurous you are, and whether you want to reduce the number of hotel changes that require moving luggage and unpacking and repacking.

If you want to reduce the number of hotel changes, and don’t feel too adventurous ➡️ I suggest staying two nights in Florence and treating Bologna as a day trip.

You’ll need to wake early on day 5, however, to make the two hour, fifteen minute train journey to Venice.

If you want to reduce the number of hotel changes, and you don’t mind storing your luggage, or if you want to maximize the amount of time you have in Venice ➡️

I suggest checking out of your Florence hotel on the morning of day 4, taking the 40 minute train ride to Bologna, and then storing your luggage while you explore the city.

In the evening, retrieve your luggage and take the train directly to Venice, which will last about an hour and a half.

If you don’t mind hotel changes, and enjoy spending a night in each destination, then find a great hotel in Bologna and enjoy the evening there!

Day 4 – Bologna

Join a guided walking tour through Bologna to learn about its rich medieval history

Visit the Archiginnasio Palace and Anatomical Theatre
Enjoy a lunchtime food tour of Bologna’s Quadrilatero Market district
Sip on an aperitivo of natural wine before heading to dinner

BOLOGNA DOESN’T GET AS MUCH ATTENTION AS IT SHOULD, BUT IT’S AN AMAZING CITY WITH SO MUCH TO EXPLORE.

It also sits right along the path from Florence to Venice, and skipping it just seems like missing out on a quintessential Italian experience.

It’s a university town with a strong local identity, miles of ornate porticoes, and amazing food, and just the right amount of grit.

A morning walking tour is a great way to get your bearings and understand why this city is called La Dotta, La Grassa, e La Rossa (“The Learned, The Fat, and The Red”).

Swing by the Archiginnasio Palace to see both the Anatomical Theatre and the ornate 16th century library.

For lunch, dig into Bologna’s culinary heritage with a food tour through the stalls at the Quadrilatero Market.

In the early evening, stroll the porticoes and settle in for an aperitivo of natural wine — my favorite spot is Enoteca Storica.

Day 5 – Venice

Walk across the Rialto Bridge and explore St. Mark’s Square
Tour St. Mark’s Basilica and the Doge’s Palace, two of Venice's most iconic landmarks
Head to the Dorsoduro district for a cicchetti lunch and a quick visit to the Peggy Guggenheim Collection
End your Italy trip with a gondola ride at dusk followed by dinner at a hidden gem restaurant

VENICE MIGHT JUST BE THE MOST MAGICAL, SURREAL CITY IN THE WORLD.

Be sure to take a train that arrives at Venezia Santa Lucia, directly in the historic sestieri of Canneregio.

Begin your visit by walking across the Rialto Bridge toward St. Mark’s Square.

Take a tour of St. Mark’s Basilica and Doge’s Palace early, before the cruise ship crowds set in.

Then escape to Dorsoduro for a cicchetti lunch at Osteria al Squero and a peek into the bold, modern art displayed at the Peggy Guggenheim Collection.

In the evening, book a gondola ride timed for sunset.

Yes, it’s touristy, but it’s a great final experience from your Italian adventure!

FINALLY, SEEK OUT A HIDDEN GEM RESTAURANT FOR A FINAL DINNER YOU’LL BE THINKING ABOUT ON THE FLIGHT HOME.

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Places to Skip on Your 5 Day Italy Itinerary

Short on time? You can skip these spots without feeling FOMO or guilt:

Cinque Terre: A darling of the 2010s, but today it’s overtouristed and no longer a rewarding cultural stop. Unless you’re staying overnight and hiking, Cinque Terre can be skipped.
Milan: Yes, the Last Supper is here. But unless shopping is your primary vacation goal, Milan can be saved for a return visit. Do it when you have time to complement the capital with a visit to the Dolomites, Verona, or Turin.

Amalfi Coast: This is an absolutely stunning destination, so much so that it deserves its own dedicated trip. Don’t treat Amalfi like a side quest, instead, group it together with a visit to Naples.
Pisa: The Leaning Tower is fun for a photo op, but this is not a must-do for a first visit to Italy. There are better uses of your time.

Conclusion

Five days in Italy will fly by — but with a little bit of smart planning, you’ll be able to experience the country’s most iconic cities, flavors, and sights without spreading yourself too thin.

Focus on quality over quantity, and leave space in your itinerary for spontaneity.

WHETHER THAT’S A LONG LUNCH OR A LATE-NIGHT WALK, REMEMBER: YOU CAN ALWAYS COME BACK.

Italy rewards repeat visits, and if you follow this itinerary, I’m sure you’ll already start dreaming about your next visit to Italy before your plane even takes off. ✈️

Until next time,

Angela

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