Italy, a country renowned for its rich history, stunning landscapes, and world-class cuisine, offers a plethora of experiences for travelers. From the bustling streets of Milan, known for its fashion and design, to the tranquil beauty of Lake Como, Italy's northern regions are a blend of modernity and tradition. As you journey south, the ancient ruins of Rome, the Renaissance art of Florence, and the medieval charm of Siena await. The Amalfi Coast and Positano offer breathtaking coastal views, while Naples is a gateway to the vibrant culture of southern Italy. Finally, the sun-drenched region of Apulia, with its unique trulli houses and olive groves, provides a perfect conclusion to this Italian adventure.

This 16-day itinerary is designed to give you a taste of Italy's diverse regions, with a mix of cultural, historical, and culinary experiences. Whether you're exploring the art galleries of Florence, savoring a Neapolitan pizza in Naples, or relaxing on the beaches of the Amalfi Coast, each destination offers something unique.

Milan, Lombardy, Italy

Days 1-2

Arrive in Milan, Italy's fashion capital, known for its high-end shopping, stunning architecture, and vibrant cultural scene. Spend your first afternoon settling into your accommodation. For the best places to stay, consider using VRBO or Hotels.com.

On your first full day, explore the iconic Duomo di Milano and the Galleria Vittorio Emanuele II. Don't miss the chance to see Leonardo da Vinci's "The Last Supper" with a guided tour. Consider booking the Last Supper and S. Maria delle Grazie skip the line Tickets and Tour for an unforgettable experience.

For dinner, indulge in traditional Milanese cuisine at Trattoria Milanese or Ristorante Cracco. In the evening, explore the vibrant nightlife in the Brera district.

Como, Lombardy, Italy

Days 3-4

Travel to Como, a picturesque town on the shores of Lake Como, known for its stunning villas and serene landscapes. The best way to travel is by train, which takes about an hour from Milan. Use Omio for train bookings.

Spend your days exploring the charming town of Como, taking a boat tour on the lake, and visiting the beautiful Villa del Balbianello. For accommodations, check out VRBO or Hotels.com.

For dining, try Osteria del Gallo for authentic Italian dishes. In the evening, enjoy a leisurely stroll along the lakefront promenade.

Rome, Lazio, Italy

Days 5-7

Head to Rome, the Eternal City, where ancient history and modern life coexist. The train from Como to Rome takes approximately 3.5 hours. Book your tickets through Omio.

In Rome, visit iconic landmarks such as the Colosseum, Roman Forum, and Vatican City. Consider a guided tour of the Vatican Museums and Sistine Chapel, such as the Vatican Museums, Sistine Chapel & St Peter’s Basilica Guided Tour.

Stay in the historic center for easy access to attractions. Use VRBO or Hotels.com for accommodations.

For dining, try Trattoria da Enzo al 29 for traditional Roman cuisine. In the evenings, explore the lively Trastevere neighborhood for bars and nightlife.

Florence, Tuscany, Italy

Days 8-10

Travel to Florence, the cradle of the Renaissance, known for its art, architecture, and vibrant culture. The train from Rome to Florence takes about 1.5 hours. Book your tickets through Omio.

Visit the Uffizi Gallery, Accademia Gallery, and the iconic Florence Cathedral. Consider a guided tour like the Skip the line: Uffizi and Accademia Small Group Walking Tour.

Stay in the city center for easy access to attractions. Use VRBO or Hotels.com for accommodations.

For dining, try Osteria Vini e Vecchi Sapori for authentic Tuscan dishes. In the evenings, enjoy a sunset walk along the Arno River.

Siena, Tuscany, Italy

Days 11-12

Travel to Siena, a charming medieval city known for its historic center and the Palio horse race. The best way to travel is by bus or train from Florence, taking about 1.5 hours. Use Omio for bookings.

Explore the Piazza del Campo, Siena Cathedral, and the Torre del Mangia. Consider a wine-tasting tour in the surrounding Chianti region, such as the Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena.

Stay in the historic center for easy access to attractions. Use VRBO or Hotels.com for accommodations.

For dining, try Osteria Le Logge for traditional Sienese cuisine. In the evenings, enjoy a leisurely stroll through the medieval streets.

Positano and Amalfi Coast

Days 13-14

Travel to Positano, a picturesque village on the Amalfi Coast, known for its colorful buildings and stunning views. The best way to travel is by train to Salerno and then a ferry to Positano. Use Omio for bookings.

Spend your days exploring the Amalfi Coast, visiting nearby towns like Amalfi and Ravello. Consider a boat tour, such as the Small-Group Amalfi Coast Day Cruise from Positano.

Stay in Positano for easy access to the coast. Use VRBO or Hotels.com for accommodations.

For dining, try Ristorante La Sponda for a romantic dinner with a view. In the evenings, enjoy the vibrant nightlife along the coast.

Naples, Campania, Italy

Days 15-16

Travel to Naples, a city known for its rich history, vibrant culture, and delicious cuisine. The best way to travel is by ferry from Positano to Naples. Use Omio for bookings.

Explore the historic center, visit the Naples National Archaeological Museum, and indulge in authentic Neapolitan pizza. Consider a day trip to Pompeii, such as the Pompeii Vesuvius Day Trip from Naples & Italian Light Lunch.

Stay in the city center for easy access to attractions. Use VRBO or Hotels.com for accommodations.

For dining, try Pizzeria Da Michele for a classic Margherita pizza. In the evenings, explore the lively streets of the Spanish Quarter.

Apulia, Italy

Days 17-18

Conclude your journey in Apulia, a region known for its stunning coastline, historic towns, and delicious cuisine. The best way to travel is by train from Naples to Bari. Use Omio for bookings.

Explore the charming towns of Alberobello, known for its trulli houses, and Matera, a UNESCO World Heritage site. Consider a guided tour of the region, such as the Vatican Museums, Sistine Chapel & St Peter’s Basilica Guided Tour.

Stay in a traditional trullo for a unique experience. Use VRBO or Hotels.com for accommodations.

For dining, try Ristorante Grotta Palazzese for a unique dining experience in a cave overlooking the sea. In the evenings, enjoy the relaxed atmosphere of the coastal towns.

This 16-day itinerary offers a comprehensive exploration of Italy's diverse regions, from the fashion-forward streets of Milan to the sun-drenched shores of Apulia. Each destination provides a unique blend of history, culture, and cuisine, ensuring an unforgettable Italian adventure.