Italy is a dream destination, offering everything from historical landmarks to coastal paradise and world-class cuisine. This 9-day itinerary takes you through Cinque Terre, Milan, Florence & Tuscany, Rome, and the Amalfi Coast, with a delicious stop in Naples for authentic pizza. With efficient train and flight connections, you’ll maximize your time while immersing yourself in the best Italy has to offer.
Day 1-2: Milan & Lake Como
For Arrival & Transportation, Fly into Milan Malpensa Airport (MXP) or Linate Airport (LIN) and take the Malpensa Express train (50 min) to Milan Centrale station.
Things to do in Milan:
Visit the Duomo di Milano and climb to the rooftop. Admire Galleria Vittorio Emanuele II for luxury shopping and architecture. See Leonardo da Vinci’s Last Supper (book tickets in advance). Stroll through Sforza Castle and Parco Sempione.
Optional Day Trip: Lake Como
Take a 40-minute train from Milan Centrale to Varenna. Explore Bellagio, the famous town along the lake, by ferry. Return to Milan in the evening.
Day 3: Cinque Terre
To get there, Take a 3-hour train from Milan to Monterosso al Mare (via La Spezia). Cinque Terre is best explored by train; get the Cinque Terre Train Card.
Top Things to Do
Hike between the villages (Monterosso → Vernazza → Corniglia). Relax on the beaches of Monterosso. Catch sunset views in Manarola with a glass of local Sciacchetrà wine. Enjoy seafood pasta in Riomaggiore. Stay overnight in Monterosso or Vernazza.
Day 4-5: Florence & Tuscany
To get there, take a 2.5-hour train from La Spezia to Florence.
Day 4: Florence Highlights
Visit Piazza del Duomo and climb Brunelleschi’s Dome. See Michelangelo’s David at the Accademia Gallery. Walk across Ponte Vecchio and explore the Uffizi Gallery. Sunset at Piazzale Michelangelo.
Day 5: Tuscany Day Trip
Book a tour to visit San Gimignano (medieval town with stunning towers), Chianti wine region (wine tasting at a vineyard), and Siena (beautiful Piazza del Campo). Return to Florence for the evening and stay overnight.
Day 6: Rome
To get there, take a 1.5-hour high-speed train from Florence to Rome.
Rome Highlights
Visit the Colosseum & Roman Forum. Walk around Piazza Venezia & Trevi Fountain. Explore the Pantheon and Piazza Navona. Dinner in Trastevere, one of Rome’s most charming neighborhoods. Stay overnight in Rome.
Day 7: Vatican City & Naples Pizza Stop
Morning: Vatican City
Visit St. Peter’s Basilica (climb the dome for views). Explore the Vatican Museums & Sistine Chapel (book skip-the-line tickets).
Afternoon: Naples Pizza Stop
Take a 1-hour high-speed train from Rome to Naples. Eat authentic Neapolitan pizza at L’Antica Pizzeria da Michele or Sorbillo. Walk along Spaccanapoli before heading to the Amalfi Coast.
Evening: Travel to Positano
Take the Circumvesuviana train (1 hour) to Sorrento, then a ferry or bus to Positano. Stay overnight in Positano. You can also book a private transfer as well.
Day 8: Positano & Capri
Morning: Explore Positano
Walk down the iconic cliffside streets. Relax on Spiaggia Grande beach. Enjoy breakfast at Casa e Bottega.
Afternoon: Capri Day Trip
Take a 30-minute ferry from Positano to Capri. Visit Blue Grotto (if the sea conditions allow). Take the chairlift up to Monte Solaro for panoramic views. Explore Piazzetta di Capri and Anacapri. Return to Positano in the evening by ferry. (book tickets ahead of time) Stay overnight in Positano.
Day 9: Return to Rome & Fly Home
Getting Back
Take a ferry or bus to Naples. From Naples, take a 1-hour high-speed train to Rome Termini. Fly out of Rome Fiumicino Airport (FCO).
Bonus Option: Venice (If You Have Extra Time!)
How to Add Venice (Before it Sinks)
Instead of going straight to Milan on Day 1, take a 2.5-hour train from Milan to Venice. Spend 1-2 days in Venice, then take a 3-hour train to Milan to continue the itinerary.
Top Things to Do in Venice
Ride a gondola along the Grand Canal. Explore St. Mark’s Basilica & Piazza San Marco. Visit the Doge’s Palace & Bridge of Sighs. Take a boat trip to Burano & Murano islands. After Venice, take a train to Milan and continue the original itinerary.
Final Tips for This Italy Itinerary
Best Time to Visit: Spring (April-June) or Fall (September-October) for great weather and fewer crowds.
Trains & Flights: Use Trenitalia or Italo for high-speed trains. Book in advance for the best prices.
Packing: Bring comfortable shoes—Italy involves a lot of walking!
This 9-day itinerary balances history, culture, breathtaking landscapes, and, of course, amazing Italian food. Are you ready for the trip of a lifetime?
