Milan to Naples: Italy's Most Iconic Cities by Train

Your Italian adventure begins in Milan, Italy’s fashion capital and gateway to the north. Arrive at Milano Malpensa Airport and enjoy a smooth check-in at your hotel, conveniently located nearby.

Take time to rest and recover from your travels, because tomorrow, la dolce vita officially begins.

Accommodation: Sheraton Milan Malpensa Airport Hotel (or comparable lodging).

After a warm welcome and morning briefing from one of our friendly, English-speaking local guides, head straight into Milan’s historic core.

Start your guided tour in Milan with a visit to the Duomo di Milano rooftop, where spires soar above the skyline, then stroll through the stunning Galleria Vittorio Emanuele II — a 19th-century marvel of iron and glass. We continue to the Castello Sforzesco, once the stronghold of the powerful Sforza family and a symbol of Milanese pride.

In the evening, see Milan from a different angle during a Navigli canal cruise, gliding past art studios and wine bars as locals gather for aperitivo.

Maybe sip on a Negroni or chilled Franciacorta while sampling bite-sized local delights.

Treat yourself to dinner and savor Risotto alla Milanese infused with saffron, the tender richness of Ossobuco, or a golden Cotoletta alla Milanese, a beloved veal cutlet that defines Milanese tradition.


Meals Included: Breakfast.

Accommodation: Hotel dei Cavalieri (or comparable lodging).

Today, board a scenic regional train to the postcard-perfect town of Como. Explore the charming old town and its stunning Duomo, a masterwork of Gothic and Renaissance design.

Then, embark on a leisurely Lake Como cruise, drifting past stately villas and alpine scenery. Disembark in Bellagio, the “Pearl of the Lake,” where cobbled lanes and floral balconies await.

Sip espresso on a terrace or browse silk boutiques as church bells echo through the hills.

Return to Milan by boat and train.

Meals included: Breakfast.

Accommodation: Hotel dei Cavalieri (or comparable lodging).

Hop aboard the Frecciarossa high-speed train to Verona, the city of star-crossed lovers. Follow your Guide through Piazza delle Erbe, see the ancient Roman Arena, and pause beneath Juliet’s Balcony, where Shakespearean legend lingers.

Maybe stop for lunch and perhaps taste bigoli pasta with duck ragù or Verona’s own risotto all’Amarone.

In the afternoon, continue the journey to Venice, with its hidden corners and sunlit canals. As the city glows golden, enjoy the atmosphere of Venice’s maritime soul.


Meals included: Breakfast.

Accommodation: Hotel Palazzo Odoni (or comparable lodging).

After breakfast, your half-day guided tour in Venice starts. Step back in time at the Doge’s Palace, where the rulers of Venice held court, and visit the majestic St. Mark’s Basilica, shimmering with golden mosaics.

Cross the lagoon to Murano for a glass-blowing demonstration, where artisans shape molten beauty using centuries-old techniques.

In the afternoon, maybe take a gondola ride, stop at a café with Spritz and cicchetti (Venetian tapas), or shop for Murano glass and Carnival masks.

Looking for dinner suggestions? Think spaghetti al nero di seppia (squid ink pasta), fried mozzarella in carrozza, or fresh Adriatic seafood — paired, of course, with a crisp local Prosecco.


Meals included: Breakfast.

Accommodation: Hotel Palazzo Odoni (or comparable lodging).

This morning, travel by train to Florence, the cradle of the Renaissance. After checking in, take a moment to soak in the city’s charm — from sun-dappled piazzas to artisan boutiques and elegant cafés.

Treat yourself to a relaxed Tuscan lunch, perhaps a fresh pappardelle al cinghiale or a glass of Chianti, and enjoy the vibrant atmosphere of Florence’s historic center.

In the afternoon, meet your expert local guide for a private walking tour through Florence’s timeless treasures. Admire the majestic Duomo, cross the storied Ponte Vecchio, and visit Santa Croce, the final resting place of Michelangelo and Galileo.

You must end the day with a classic Bistecca alla Fiorentina — a flame-grilled T-bone steak — in a cozy, historic trattoria.


Meals included: Breakfast.

Accommodation: Grand Hotel Baglioni (or comparable lodging).

Today, head into Tuscany’s rolling hills on a day trip to Siena. Walk through the stunning Piazza del Campo, home of the famous Palio horse race, and admire the striped marble Cathedral — a Gothic marvel.

In this region of earthy elegance, food is simple and sublime: pici pasta with wild boar ragù, wedges of pecorino cheese, and rustic bread soaked in rich olive oil.

The journey continues with a wine tasting at a countryside vineyard. Sample Chianti Classico, Brunello di Montalcino, and soak in the slow life.

Return to Florence for a beautiful evening and a delicious dinner that leaves us full, happy, and steeped in Tuscan charm.

Meals included: Breakfast.

Accommodation: Grand Hotel Baglioni (or comparable lodging).

This morning, board the high-speed train to Rome, where past and present blend seamlessly. Take time to enjoy lunch al fresco, perhaps a plate of cacio e pepe or a slice of Roman pizza, and soak in your first impressions of the Eternal City.

In the afternoon, meet your local English-speaking guide for an immersive walking tour through Ancient Rome. Step onto the Colosseum’s arena floor, retracing the footsteps of gladiators, then wander through the timeworn stones of the Roman Forum, the heart of the empire where orators, emperors once gathered.

Feel the heartbeat of history as you stand where Caesar walked.

Then, unwind with dinner, maybe near Piazza Navona, dining under glowing lanterns.

Dishes like carbonara, amatriciana, supplì, or carciofi alla romana bring Rome’s soul to our plates.

Meals included: Breakfast.

Accommodation: Hotel Lunetta (or comparable lodging).

Enter the spiritual and artistic heart of Italy with a visit to the Vatican Museums, Sistine Chapel, and St. Peter’s Basilica. Stand in awe beneath Michelangelo’s frescoes, marvel at Bernini’s grand altar, and feel the sacred hush of centuries.

As evening sets in, discover Trastevere, Rome’s bohemian neighborhood of cobblestone alleys and trattorias. Share laughter and stories over saltimbocca alla romana, gnocchi, and a bottle of local red, as timeless and heartfelt as the Eternal City itself.

Meals included: Breakfast.

Accommodation: Hotel Lunetta (or comparable lodging).

Your final rail journey brings you south to Naples, birthplace of pizza and gateway to the Mediterranean. Meet your guide for a street food tour — featuring pizza margherita, sfogliatella, and espresso so strong it sings — or a visit to Castel dell’Ovo, the city’s oldest castle set against a sparkling sea.

Afterward, explore the Pietrarsa Railway Museum, where steam engines and history converge by the Bay of Naples — a hidden gem for culture and train lovers alike.

Return to Rome for your final evening in Italy, full of flavors and stories to last a lifetime.
After dinner, head to your hotel, nicely located at Rome Fiumicino Airport. 

Meals included: Breakfast.

Accommodation: Hilton Garden Inn Rome Fiumicino (or comparable lodging).

After breakfast, without any stress, head to the airport, reachable in 10 minutes with a free shuttle, for your journey home.

But don’t be surprised if Italy has left a permanent mark on your heart — in the taste of fresh pasta, the echo of church bells, the scent of coffee, or the warmth of la dolce vita.


As Italians say, torna presto — come back soon.

Meals included: Breakfast.