How to Spend 2 Weeks in Italy: DIY Itinerary

Getting to visit Italy is a dream come true, but planning out how to see all the sights in one fortnight can be tough. After all, you can’t miss the capital city of Rome, which hosts such landmarks as the Sistine Chapel and the Colosseum, or the romantic cities of Verona and Venice, where Shakespeare’s stories and gondola rides rule.

You’ll also want to enjoy the fashion of Milan, the beauty of Tuscany, the classic pizza in Naples and the history of Pompeii. Use this 2 weeks in Italy itinerary to plan your perfect trip that hits all the highlights of Italy without missing a thing.

2 Weeks in Italy Itinerary

• Day 1: Arrive in Milan, sleep in Milan
• Day 2: Train to Venice via Verona, sleep in Venice
• Day 3: Explore Venice, sleep in Venice
• Day 4: Train to Vernazza, sleep in Vernazza
• Day 5: Explore Cinque Terre, sleep in Vernazza
• Day 6: Train to Florence via Pisa, sleep in Florence
• Day 7: Explore Florence, sleep in Florence
• Day 8: Siena/Tuscany day trip, sleep in Florence
• Day 9: Train to Naples (or Sorrento), sleep in Naples (or Sorrento)
• Day 10: Explore Naples and Pompeii day trip, sleep in Naples (or Sorrento)
• Day 11: Capri or Amalfi Coast day trip, sleep in Naples (or Sorrento)
• Day 12: Train to Rome, sleep in Rome
• Day 13: Explore Rome, sleep in Rome
• Day 14: Explore Rome, sleep in Rome
• Day 15: Fly home

Milan (1 Night)

Begin your Italian adventure in the city of Milan, a destination synonymous with finances and fashion. Milan was damaged heavily during World War II, but was rebuilt to be a grand city with plenty of history. You won’t want to miss the amazing museums, including the Pinacoteca di Brera and the Leonardo da Vinci Museum of Science and Technology.

Then, climb to the roof of the Duomo, a 14th century cathedral, and soak in views of the entire city. Don’t leave Milan without seeing a live performance at La Scale Theater, strolling through the Piazza del Duomo or shopping at the ritzy Galleria Vittorio Emanuele.

See also: Where to Stay in Milan

Verona (stopover)

On your way from Milan to Venice, spend some time in the city of Verona. This city of love was the setting for Shakespeare’s Romeo and Juliet, and you can actually tour Casa di Giulietta, which is now a symbol of romance and eternal love.

Verona also boasts a number of Roman ruins, like the amphitheater that is one of the world’s largest and was built nearly 2,000 years ago. Round out your stay with some window shopping along the Via Mazzini, a pedestrian-friendly stretch of upscale Italian boutiques.

Venice (2 nights)

As arguably one of the most scenic cities on the planet, Venice definitely deserves a spot on your Italy itinerary. Built on a lagoon, Venice is surrounded by water, which means that scenic bridges, water taxis and gondolas are all around you. The hub of the city is the Piazza San Marco, where you will also find the incredible Saint Mark’s Basilica and the Palazzo Ducale.

Be sure to soak in the sights from the Rialto Bridge, which is more than 800 years old, or the Rialto Market, which boasts everything from antiques to cheap souvenirs.

See also: Where to Stay in Venice

Vernazza (2 nights)

Cinque Terra, or five lands, is one of the most scenic destinations in all of Italy. Made up of five different villages along the coast, Cinque Terra boasts cliffs that head straight into the sea, some of the best coastal hiking in all of Europe, sand and pebble beaches ideal for swimming and a vibrant culture that almost feels removed from mainland Italy.

One of the villages, Vernazza, makes a fantastic home base for your two nights in the area. In Vernazza, be sure to hike the 90 minutes to Monterosso, try a slice of the local pesto pizza and sip the ubiquitous wine of the area, called Vino de la Cinque Terre.

Florence (3 nights)

Next up is Florence, the Renaissance city that is known the world over for its incredible architecture. For art lovers, the number one stop in Florence should be the Uffizi Gallery, which boasts an amazing collection of paintings by European masters like Titian and Botticelli. Other great museums in the city include the Pitti Palace, the Gucci Museum and the Bargello.

Stroll through the old town center to see the Duomo di Firenze, complete with a dome by Brunelleschi, the Giotto Tower, the Palazzo Vecchio and the bustling Mercato del Porcellino, a market filled with vendors from throughout the region. We recommend spending 3 nights here of your 2 weeks in Italy.

Tuscany (day trip from Florence)

While you’re staying in Florence, sneak away for a day trip to see more of what Tuscany has to offer. The province of Tuscany is well known for its incredible selection of wines and delicious food, so come hungry to make the most of it all.

You might head to Pisa to spot the famed leaning tower, you could do some wine tasting in the vineyards of Chianti or you could tour through ancient Roman ruins in the city of Lucca.

Naples (3 nights)

Naples boasts the designation of being one of the oldest cities in the Western World as well as the birthplace of pizza. While you’re there, start with a tour of the Castel dell’Ovo at Porto Santa Lucia, an unusually shaped castle that houses the Museum of Prehistory.

Then, make your way to the Duomo, the largest cathedral in Naples and the site of some Roman ruins. After some sightseeing in Naples, make your way to a pizzeria and order the classic pizza margherita, which comes topped with tomatoes, olive oil, fresh basil and mozzarella cheese.

See also: Where to Stay in Naples

Pompeii (day trip from Naples)

A great day trip from Naples is Pompeii, the ruined city that was engulfed after an explosion from nearby Mt. Vesuvius nearly 2,000 years ago. In Pompeii, you can walk through the ruins and see a number of incredible structures that are amazingly well preserved given their age. Among the landmarks include the amphitheater, which could seat more than 20,000 people, the House of the Vetti, the Basilica, the Forum Granary and several public bathhouses.

You can walk along the same streets as the residents of Pompeii did two millennia ago, and you can also visit the National Archaeological Museum to see the site’s most impressive remains and artifacts.

Amalfi Coast (day trip from Naples)

To see some of the most beautiful scenery in all of Italy, and to live the high life for a day, head to the Amalfi Coast. The area is the perfect spot for a day trip from Naples, letting you see some of the most famous beaches without paying a fortune for coastal accommodation.

You can tour a number of historic churches and landmarks in the area, but the real draw to the Amalfi Coast is the coast, the beach and the opportunities to rent yachts, sip cocktails overlooking the water and stay active in the sunshine. There are a number of beautiful villages along the Amalfi Coast, just some of which include Positano, Cetara and Amalfi itself.

Rome (3 nights)

Of course, absolutely no getaway to Italy would be complete without spending time in Rome. The Eternal City, as it is known, is the heart of Western civilization, and it boasts world-class museums like the Galleria Borghese and the Capitoline Museums.

You can also admire the Sistine Chapel in Vatican City, stroll through the ruins of the Colosseum and spot landmarks like the incredible Trevi Fountain. Rome also offers amazing shopping along streets like via del Corso and via Condotti, and the nightlife in areas like Testaccio is not to be missed.