Italy trip: Authentic city experiences

Arrive in Milan and settle into your hotel. Start your Italy travel with a short stroll to the Duomo to admire its soaring Gothic façade and rooftop panoramas. Explore the interior and snap photos of the piazza.

Pause for a relaxing coffee at a nearby café, then savor dinner at a family-run trattoria serving regional specialties.

Start the day with a tailored visit to the historic Sforza Castle to explore impressive art collections. See Leonardo da Vinci’s The Last Supper at Santa Maria delle Grazie with reserved access and expert commentary. For travelers looking to extend their journey beyond Milan, an Italian lakes trip offers a scenic complement to the city experience.

In the afternoon, wander the refined Brera district to browse galleries and cozy cafés, then discover Milan’s renowned fashion scene in the Quadrilatero della Moda for exclusive shopping and style insights.

Catch a high speed train from Milan to Venice, arriving in about two and a half hours. Relax in modern comfort and watch the Lombardy countryside unfold as your tailor-made Italy trip moves to the iconic lagoon city.

Explore St. Mark's Square, wander hidden sestieri with a local guide, glide on a gondola at sunset, and taste Venetian cicchetti at family run bacari.

Wander Venice's winding alleyways, discover hidden squares and lively markets with a local guide for an authentic, tailor-made Italy trip experience.

In the afternoon, glide on a vaporetto along the Grand Canal to admire palaces and bridges from the water, then finish with a relaxed dinner by the canals curated to your tastes.

Step into Venice's history at the Doge's Palace, cross the Bridge of Sighs, and glide along serene canals on a private gondola for an unforgettable perspective.

Next, wander Cannaregio's narrow lanes and local markets, then end the Venice part of your trip with dinner at a traditional Venetian osteria, savoring seafood risotto and authentic regional flavors.

Catch a high-speed train from Venice to Bologna, enjoying scenic lagoon and countryside views. Arrive in Bologna and check into your hotel. Spend the afternoon wandering historic streets, admiring medieval towers and Piazza Maggiore, and exploring porticoes, hidden courtyards, and lively markets.

In the evening, savor traditional Bolognese dishes like tagliatelle al ragù at a family-run trattoria in the city center, paired with local wine and warm hospitality.

Begin your day in the Quadrilatero district, tasting fresh local produce, cured meats, and cheeses, then visit the Basilica di San Petronio and climb the Asinelli Tower for sweeping city views.

In the afternoon, stroll along the Portico di San Luca, soaking in Bologna's graceful architecture and lively atmosphere.

Arrive in Florence by train from Bologna and check into your accommodation. After a short rest, enjoy a guided or self-paced stroll to Piazza del Duomo to admire the Cathedral and Baptistry up close and capture timeless views.

In the evening, dine at a family-run trattoria to savor Tuscan specialties like ribollita and bistecca alla Fiorentina, with local wine pairings and insider recommendations for your next days.

Visit the Uffizi Gallery to admire Botticelli, Da Vinci, and Raphael, then wander Piazza della Signoria and Palazzo Vecchio to experience authentic Florence, a perfect introduction for anyone planning a trip to Florence.

Climb to Piazzale Michelangelo for sweeping views, enjoy a creamy gelato, and stroll along the Arno River.

Take the train to Pisa for a half-day trip. Visit the Leaning Tower of Pisa, capture iconic photos, and admire medieval architecture in Piazza dei Miracoli, including the Pisa Cathedral and Baptistry.

In the afternoon, stroll along the Arno River, taste authentic gelato, and soak up local atmosphere before returning to Florence for the night.

Board a high-speed train from Florence to Rome, gliding past rolling Tuscan hills on a smooth, efficient transfer that saves time and showcases the landscape. Upon arrival, dive straight into ancient Rome.

Step inside the Colosseum, walk the ruins of the Roman Forum, and climb Palatine Hill for sweeping views over the Eternal City. Then refuel with authentic Roman pizza at a local trattoria: simple, crisp, and just the way the locals like it.

Spend the day in Vatican City. Marvel at St. Peter's Basilica and climb the dome for sweeping views. Explore the Vatican Museums and end in the Sistine Chapel to admire Michelangelo's frescoes.

As dusk falls, wander Trastevere's cobbled streets and savor classic Roman cuisine in intimate trattorias.

Visit the Pantheon and toss a coin into the Trevi Fountain to promise a return. Stroll lively Piazza Navona and savor a classic gelato at Giolitti.

Pause on the Spanish Steps for a final peaceful moment and reflect on handcrafted experiences from your Italy itinerary.

Today, your journey through Italy comes to a close. From Venice’s canals to Florence’s art-filled streets and the charm of Tuscany’s hills, you’ve uncovered the rich layers of Italy’s most iconic cities.

After breakfast, a private transfer will take you to the airport for your flight home, bringing with you unforgettable moments, countless stories, and a lasting taste of la dolce vita.