The Ultimate 2-Week Italy Itinerary: Sights, Pasta, and Plenty of Gelato

Well, two weeks in Italy! That’s just enough time to leave you utterly obsessed and already planning your return. Italy is like a buffet where everything looks so good, you don’t know where to start—but I’ve got you covered. Here’s a witty, delicious itinerary that ensures you see Italy’s greatest hits (while making time for la dolce far niente, of course).

Day 1-3: Rome – The Eternal City

Where better to kick things off than Rome, where ancient history and modern life collide in the most spectacular fashion? Rome is like that one friend who can’t stop telling you about their glory days—and honestly, they’ve earned it.

Colosseum: Start your trip with the big guns. Stand in awe of the sheer size and imagine gladiators fighting while you wonder how people lived without Wi-Fi.
Roman Forum: It’s like wandering through the set of a history movie, but it’s real. The ruins of ancient government buildings will make your daily commute feel pretty insignificant.
Vatican City: Pop over to the world’s smallest country (yes, it’s its own country!). The Sistine Chapel ceiling will give you a permanent crick in your neck, but Michelangelo’s genius is worth it. Bonus: wave at the Pope!
Trevi Fountain: Throw a coin in (with your right hand over your left shoulder, don’t mess this up) to ensure you return to Rome. Because you’ll want to.

Pro tip: After all that walking, treat yourself to the best gelato in town at Gelateria del Teatro. You earned it.

Day 4-5: Florence – Art, Culture, and More Gelato

Next, hop on a train to Florence. The birthplace of the Renaissance is all about art, food, and climbing things to get incredible views. Prepare to have your mind blown by more masterpieces than you can count.

The Duomo: Climb to the top for stunning views of the city (and to burn off that extra gelato from Rome). The dome is as impressive from the inside as it is outside.
Uffizi Gallery: Art nerds, rejoice. From Botticelli’s “The Birth of Venus” to da Vinci’s works, it’s like walking through art history 101—but way cooler.
Ponte Vecchio: Stroll across this iconic bridge that’s lined with shops, and maybe splurge on some jewelry (or just a postcard if you blew all your money in Rome).
Piazzale Michelangelo: For a panoramic view of Florence at sunset, this spot is unbeatable. You’ll feel like you’re in a postcard—minus the cheesy writing.

Pro tip: Head to All’Antico Vinaio for a sandwich that’s bigger than your head and probably tastier than anything you’ve ever had.

Day 6-8: Tuscany – Rolling Hills and Wine (Lots of Wine)

After Florence, you deserve some time in the Tuscan countryside. Rent a car (or book a tour if you’d rather not navigate Italy’s creative driving style) and head out to the rolling hills, vineyards, and charming towns that feel straight out of a movie.

Siena: A medieval gem with a stunning piazza (Piazza del Campo) and a gorgeous cathedral (yes, another one—but it’s worth it).
San Gimignano: The town of towers. Wander through the cobblestone streets, eat more gelato (Gelateria Dondoli is world-famous), and climb one of the towers for views that stretch forever.
Chianti Wine Region: Tuscany is synonymous with wine, so it’s practically your duty to visit a vineyard. Sample the local Chianti, learn about the winemaking process, and maybe buy a few bottles to “take home” (or drink later that night—no judgment).

Pro tip: Stay in an agriturismo (a farm stay) to experience true Tuscan hospitality, complete with home-cooked meals and views to die for.

Day 9-11: Venice – Romance, Canals, and Getting Lost

Next stop: the magical, sinking city of Venice. You won’t need a car here—just your feet, a map, and maybe a boat. Venice is the ultimate “get lost and love it” city.

St. Mark’s Basilica: Prepare to be dazzled by gold mosaics and architecture that’s over-the-top in the best possible way.
Rialto Bridge: Take a selfie on this iconic bridge, then spend some time browsing the markets nearby.
Gondola Ride: Yes, it’s touristy. Yes, it’s expensive. But come on, it’s Venice! You can’t leave without drifting down the canals while your gondolier serenades you (or tries, at least).
Doge’s Palace: A deep dive into Venice’s political history with a side of jaw-dropping artwork.

Pro tip: Get up early (like, before the crowds early) to experience St. Mark’s Square in peaceful, golden morning light. It’s magical.

Day 12-14: Amalfi Coast – Sun, Sea, and La Dolce Vita

End your Italian adventure on the Amalfi Coast, where the cliffs meet the sea in the most spectacular way. This is Italy at its most dramatic—both in scenery and in price tags. But it’s worth it.

Positano: The postcard town. Pastel buildings cling to the cliffs, and the beach is the perfect spot to relax and soak in the Mediterranean vibes.
Ravello: Perched high above the coast, Ravello offers stunning views and beautiful gardens (Villa Cimbrone is a must-see).
Amalfi: Take a stroll through the charming town, visit the cathedral, and enjoy some lemon sorbet made from the region’s famous limoni.
Capri: If you’re feeling fancy (and who isn’t after two weeks in Italy?), take a boat to the island of Capri. The Blue Grotto is the big draw, but exploring the island and sipping limoncello with a view isn’t a bad way to spend a day.

Pro tip: Travel light on the Amalfi Coast—those picturesque stairs are beautiful but unforgiving if you’re lugging around too much stuff!

The Bottom Line

This two-week itinerary gives you the perfect mix of history, art, food, wine, and pure relaxation. You’ll experience the chaos of Rome, the beauty of Florence, the tranquility of Tuscany, the romance of Venice, and the stunning drama of the Amalfi Coast—all while consuming more carbs than you ever thought possible.

By the end, you’ll wonder why anyone ever leaves Italy—and let’s be honest, you’ll probably start planning your next trip before you even board your flight home.